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Due to the harmful effects of chlorinated combustion products and strontium in currently used red-burning pyrotechnics on human health and the environment, new substitutes have to be found. A promising alternative could be using lithium-salts. While it is a literature-known problem that the generation of a lithium-based red flame color is a challenging task due to the diverse requirements of the Li(0) color species, a promising alternative could be using lithium-heterocycle salts. In this context, nitrogen-rich lithium tetrazole and bistetrazole salts, namely, lithium tetrazolate, lithium 5-aminotetrazolate, dilithium 5,5’-bistetrazolate dihydrate and dilithium 5,5’-bis(tetrazolate-1-oxide) have been investigated as potential replacements. To evaluate the performance of the salts a variety of mixtures were prepared and their pyrotechnic parameters were analyzed. Furthermore, application-specific pyrotechnic clusters and parachute flares were produced and these were also tested for burning time, dominant wavelength, spectral purity and luminous intensity. Observations on the use of lithiated nitrogen-rich salts in pyrotechnic mixtures showed a red color impression, indicating the potential of these mixtures. Further research opportunities can be pursued by refining nitrogen-rich compounds. [ABSTRACT FROM AUTHOR]

The rational design of a high surface area heterogeneous nanocomposite catalyst with well‐defined surface acidic sites and structural porosity is a promising approach with potential application in expeditious synthesis of biologically active molecules/scaffolds. In this work, mesoporous zirconium phosphate (m‐ZrP) was synthesized through a hydrothermal process and used as a porous matrix for dispersion of cesium‐exchanged phosphotungstic acid (CsxH3‐xPW12O40) nanoparticles to prepare CsxH3‐xPW12O40‐mZrP nanocomposite systems. Various characterization techniques, including XRD, UV–vis‐DRS, FTIR, FESEM, HRTEM, TGA‐DTA, BET, and TPD, were used to understand the structural, morphological, and surface properties of the composites. XRD analysis revealed the presence of m‐ZrP and cubic CsxH3‐xPW12O40 crystalline phases in the nanocomposite materials. A microscopic study indicated the existence of rod‐shaped morphology that was formed by the coalescence of a large number of spherical nanoparticles with diameters between 150 and 200 nm. The dispersion of CsxH3‐xPW12O40 over the m‐ZrP surface results in significant enhancement of medium and strong acidic sites, with the maximum number of acidic sites observed for the Cs0.5‐PTA‐mZrP composite (0.406 mmol g−1). The catalytic activity of the CsxH3‐xPW12O40‐mZrP nanocomposites was evaluated for rapid synthesis of tetrazole derivatives through [3 + 2] cycloaddition reactions of substituted nitrile and NaN3 under mild conditions. The detailed optimization study revealed that the use of Cs0.5‐PTA‐mZrP catalyst in DMF media afforded 90% yield of the tetrazole at 120 °C. Reaction kinetics study suggested that the optimal Cs0.5‐PTA‐mZrP catalyst exhibited the highest reaction rate of 2.06 × 10−3 mmol h−1m−2 towards tetrazole formation. Structurally diverse tetrazole derivatives in high yield and purity were synthesized under mild conditions using CsxH3‐xPW12O40‐mZrP nanocomposite as catalyst. [ABSTRACT FROM AUTHOR]

Azoxy coupling of 5‐amino‐1‐methyl‐tetrazole, 5‐amino‐2‐methyl‐tetrazole, and 5‐amino‐1‐methoxy‐tetrazole was performed by reacting each with various oxidants. These reactions revealed aqueous Oxone to be the most facile system for yielding the azoxy couple for the previously mentioned tetrazoles. Chemical and structural characterization of each novel azoxy‐coupled tetrazole was conducted with 1H NMR, 13C NMR, HRMS, and single‐crystal x‐ray diffraction. Energetic characterization was evaluated by analysis of each compounds' single crystal x‐ray diffraction density, impact sensitivity, friction sensitivity, and decomposition temperature. All compounds were found to be very sensitive to impact and friction stimuli. [ABSTRACT FROM AUTHOR]

Recently, tumor-targeted radionuclide therapy has gained much recognition for the treatment of metastasized cancer. There is a growing interest in using the theranostic radionuclide 47Sc, owing to its excellent chemical and nuclear properties. However, the available chelating agents require a relatively high temperature for their radiolabeling, which could denature biomolecules. The aim of the present study is to synthesize a dipeptide agent that forms a thermodynamically more stable complex with 47Sc at room temperature. A novel α-amino acid ester derivative attached to pyrazine and tetrazole heterocyclic rings has been prepared by the azide coupling method. Different spectroscopic methods (FT-IR, 1H NMR, and mass spectra) were used for characterization of the target compound. The newly synthesized dipeptide was radiolabeled with 47Sc, and a high radiochemical yield of 98.5 ± 1.5 % and in vitro serum stability up to 72 h were attained at room temperature within 20 min. The quantum chemical calculations at B3PW91/6-31G(d) level were employed to establish the molecular structure of the dipeptide and its complexation with 47Sc. The selectivity of 47Sc-dipeptide toward localization in tumor cells was performed by molecular docking on different receptors in addition to in vivo biodistribution on solid tumor-bearing mice. A high T/NT ratio of 8.16 was obtained after 4 h p.i, suggesting that this complex could be used as a potential cancer theranostic agent. [ABSTRACT FROM AUTHOR]

ABSTRACT Schiff‐base materials are known ligands for the coordination of metal ions and the synthesis of various stable and useful complexes. Therefore, herein, a novel Schiff‐base compound {2,2′‐((1E,11E)‐2,5,8,11‐tetra azadodeca‐1,11‐diene‐1,12‐diyl) bis (4‐bromophenol)} was introduced that formed from condensation of triethylenetetramine (TETA) and 5‐bromo‐2‐hydroxybenzaldehyde (5B2HB). This Schiff‐base ligand was labeled as TADDbBP. Besides, mesoporous MCM‐41 was synthesized using tetraethyl orthosilicate (TEOS), hydrolyzing cetyltrimethylammonium bromide (CTAB) and NaOH solution (2 M), followed by calcination at 550 °C, and further, the silanol sites on the MCM‐41's surface were modified by 3‐chloropropyltriethoxysilane (3Cl‐PTES), which modified MCM‐41 was labeled as 3‐Cl‐Pr@MCM‐41. In the next step, the synthesized TADDbBP (as Schiff‐base ligand) was grafted on 3‐Cl‐Pr@MCM‐41, which was labeled as TADDbBP@MCM‐41, and further, it was coordinated with samarium ions (which was labeled as Sm‐TADDbBP@MCM‐41 nanocatalyst) using Sm (CH3COO)3. This is the first report on the production of Sm‐TADDbBP@MCM‐41 nanocatalyst, this nanocatalyst was characterized by TEM, SEM, EDX, elemental mapping, BET method, ICP, XRD, and TGA techniques. In the final step, the catalytic performance of Sm‐TADDbBP@MCM‐41 nanocatalyst has been checked in the homo‐selective producing of tetrazoles through [2 + 3] cycloaddition of benzonitriles and sodium azide (NaN3) in PEG‐400 as available, nontoxic, green, and safe solvent. This nanocatalyst provides excellent selectivity in the synthesis of tetrazoles. In addition, Sm‐TADDbBP@MCM‐41 nanocatalyst can be separated and recycled for several cycles without significant reactivation or metal leaching. [ABSTRACT FROM AUTHOR]

Three cheap DESs comprising of N-methyldiethanolamine (MDEA) and imidazole (Im), 1,2,4-triazole, and tetrazole were investigated for capturing SO2 at low concentrations. Surprisingly, with the addition of Im, the SO2 absorption capacity and desorption efficiency were improved. Spectroscopic analysis and quantum chemical calculations confirmed that MDEA–Im effectively and reversibly captured SO2 through the hydrogen bond network and synergistic action between MDEA and Im. [ABSTRACT FROM AUTHOR]

By exploiting the chemistry of bifunctional isocyanides, straightforward, rapid, and scalable Ugi-tetrazole-based multicomponent reaction heteroannulations were developed. Our synthetic approach provides a series of diverse fused tetrazolo piperazinones and 1,4-diazepanones in just one step. [ABSTRACT FROM AUTHOR]

The magnetically recoverable heterogeneous Fe2O3@cellulose@Mn nanocomposite was synthesized by a stepwise fabrication of Mn nanoparticles on cellulose-modified magnetic Fe2O3 nanocomposites, and the morphology of the nanocomposite was characterized through advanced spectroscopic techniques. This nanocomposite was investigated as a heterogeneous catalyst for the synthesis of medicinally important tetrazole derivatives through Knoevenagel condensation between aromatic/heteroaromatic aldehyde and malononitrile followed by [3+2] cycloaddition reaction with sodium azide. Thirteen potent (E)-1-aryl-2-(1H-tetrazol-5-yl)acrylonitrile derivatives are reported in this paper with very high yields (up to 98%) and with excellent purity (as crystals) in a very short period (3 min @ 120 W) using microwave irradiation. The present procedure offers several advantages over recent protocols, including minimal catalyst loading, quick reaction time, and the utilization of an eco-friendly solvent. Furthermore, the synthesized (E)-1-aryl-2-(1H-tetrazol-5-yl)acrylonitrile derivatives (4b, 4c, and 4m) are shown to have excellent resistance against various fungal strains over bacterial strains as compared to the standard drugs Cefixime (4 μg/mL) and Fluconazole (2 μg/mL). [ABSTRACT FROM AUTHOR]

The development of efficient, and environmentally friendly catalytic systems for synthesis of 5-substituted 1H-tetrazoles is an important challenge in organic synthesis because tetrazole derivatives are well known in medicinal chemistry with many biological activities such as anti-bacterial, anti-fungal, anti-allergic, anti-viral, anti-cancer, reducing blood pressure, and so on. In this research, we fabricated a palladium(0) complex stabilized on magnetic Fe3O4 nanoparticles modified with dopamine and benzo[d]thiazole-2-carbonyl chloride [Fe3O4@SiO2-Dop/Amide-BTA-Pd(0)] (1) and evaluated its catalytic behavior in the synthesis of 5-substituted 1H-tetrazoles through one-pot tandem reactions of aryl halides with K4[Fe(CN)6] and sodium azide under eco-friendly conditions. One-pot tandem reactions of aryl halides with K4[Fe(CN)6] and sodium azide were conducted using a catalytic amount of 1 in the presence of potassium carbonate in water at 100 °C for 2 h the 5-substituted 1H-tetrazole products were obtained in high to excellent yields. At the end of the reaction, 1 can be easily recycled and the products obtained had high purity. [ABSTRACT FROM AUTHOR]

A simple method was developed for the synthesis of a new heterocyclic ensemble composed of the consecutively connected 1,2,5-oxadiazole, tetrazole, and hydroxytetrazole rings. The structure of ammonium salt of this ensemble was studied by X-ray diffraction. [ABSTRACT FROM AUTHOR]

In search for new molecules of diterpene origin with promising anticancer activity, two amino‐derivatives (methyl maleopimarate aminoimide and methyl 1β,13‐epoxydihydroquinopimarate C4‐hydrazone) were involved in the 4‐component Ugi reaction (Ugi‐4CR) and pseudo‐7‐component azido‐Ugi condensation (azido‐Ugi‐7CR) to afford a series of adducts holding α‐aminoacylamide and bis‐1,5‐disubstituted tetrazole substituents. The NCI‐60 cancer cell panel screening revealed diterpene‐type Ugi adducts 2, 5, and 6 with strong antiproliferative potency with GI50 in range of 1.2–15.4 μM. The high positive correlations with standard anticancer drugs suggest microtubules or progesterone and androgen receptors as possible targets of the synthesized compounds. [ABSTRACT FROM AUTHOR]

An intriguing trend in the synthesis of heterocyclic compounds is green chemistry, which involves using environmentally friendly reagents and efficient reactions to suit the demands of the pharmaceutical sector. This study is a part of continuous endeavour to advance novel synthetic approaches for the synthesis of heterocyclic molecules. With lanthanum nitrate hexahydrate as a catalyst, a procedure for the synthesis of tetrazoles was described in this work. The ideal 10% mole ratio of La(NO3)3·6H2O catalyst with DMF solvent produced good yields of the intended products, ranging from 85 to 98%, according to the results. High product yields, cost effectiveness, and operational simplicity are just a few benefits of using La(NO3)3·6H2O as a catalyst in this condensation reaction. The chemical structures of the synthesized tetrazoles were analyzed and characterized using 1HNMR, 13C-NMR, and mass spectra (HRMS). [ABSTRACT FROM AUTHOR]

During the last decade, research on the preparation of nano-catalysts, especially magnetic nano-catalysts, and their application in chemical reactions has become an attractive topic in organic synthesis. Nitriles are valuable compounds that are important in industrial, biological, and pharmaceutical processes. On the other hand, tetrazoles are heterocyclic compounds that have valuable pharmacological and biological properties. Therefore, developing new, environmentally friendly, and efficient catalytic systems for synthesizing nitriles and tetrazoles is needed. In this research work, we successfully fabricated Pd (0) complex immobilized on Fe3O4 nanoparticles modified with 3-amino-2-(aminomethyl)propanoic acid and imidazole [Fe3O4@SiO2-AAPA/Imid-Pd(0)] and investigated its catalytic activity in the preparation of aryl nitriles and 5-substituted-1H-tetrazoles from aryl iodides. In this attractive methodology, we first prepared different aryl nitrile derivatives from the cyanation of aryl halides and then prepared a broad range of 5-substituted-1H-tetrazoles through the condensation of the as-prepared aryl nitriles with sodium azide. The experimental results revealed that this catalyst could be reused for more than 8 consecutive runs without losing activity. Among the outstanding features of this method for the synthesis of aryl nitriles and tetrazoles, the following can be mentioned: the synthesis of products with high yields in suitable times, performing the reactions in an environmentally friendly solvent, the applicability of the method for a wide range from the substrates, easy separation of the Fe3O4@SiO2-AAPA/Imid-Pd(0) catalyst from the reaction mixture and high reusability of the catalyst. [ABSTRACT FROM AUTHOR]

A regiospecific synthesis of N9‐alkylated purines as novel acyclic nucleosides was developed. This approach is based on reconstructive methodology involving the construction of a target heterocyclic scaffold on a readily available 5‐aminotetrazole moiety, which is subsequently cleaved under reductive conditions due to azido‐tetrazole tautomerism. It appeared that the rate of reduction for the azide fragment in 6‐nitro‐7‐alkylaminotetrazolo[1,5‐a]pyrimidines is much greater than the rate of nitro group reduction. Treatment of these heterocycles with hydrogen over a palladium catalyst resulted in the formation of triaminopyrimidines in excellent yields through the reduction of both the azide and nitro group. Triaminopyrimidines were transformed into the desired N9‐alkylated purines, and an analog of the marketed drug penciclovir was synthesized by the developed method. [ABSTRACT FROM AUTHOR]

The triazole antifungals posaconazole and itraconazole can cause pseudohyperaldosteronism with hypertension and hypokalemia, edema, and gynecomastia by inhibiting steroid synthesis and metabolism. Mechanisms underlying pseudohyperaldosteronism include inhibition of adrenal 11β-hydroxylase cytochrome-P450 (CYP) 11B1 and 17α-hydroxylase (CYP17A1) as well as peripherally expressed 11β-hydroxysteroid dehydrogenase type 2 (11β-HSD2). To enhance specificity for fungal CYP51, tetrazoles have been developed. This study employed H295R adrenocortical cells and enzyme activity assays to assess the potential risk of oteseconazole and two other tetrazoles, VT-1598 and quilseconazole, to inhibit adrenal steroidogenesis or 11β-HSD2. Steroidomic footprint analyses of H295R cell supernatants using untargeted liquid-chromatography-high-resolution mass-spectrometry (LC-HRMS) indicated overall patterns common to oteseconazole, quilseconazole and itraconazole, as well as similarities between VT-1598 and isavuconazole. Additionally, more specific features of the steroid signatures were observed. Targeted quantification of nine adrenal steroids in supernatants from treated H295R cells revealed an overall inhibition of adrenal steroidogenesis by the three tetrazoles, itraconazole and isavuconazole, providing an explanation for their similar steroidomic pattern. Applying recombinant enzymes indicated that this effect is not due to direct inhibition of steroidogenic enzymes because no or only weak inhibition could be observed. Moreover, oteseconazole and the two other tetrazoles did not inhibit 11β-HSD2, suggesting that they do not pose a risk of pseudohyperaldosteronism. Furthermore, oteseconazole did not alter steroid concentrations in a recent clinical study. Nevertheless, follow-up studies should assess the mechanism underlying the observed overall steroidogenesis inhibition by tetrazoles, itraconazole and isavuconazole, and whether concentrations achievable in a subgroup of susceptible patients might cause adrenal insufficiency and hyperplasia. [ABSTRACT FROM AUTHOR]

A new composite was synthesized by modifying CoFe2O4/MCM-41 particles with N-phenyl anthranilic acid (PA) followed by treatment with Ni (II) particles. The prepared material was denoted as CoFe2O4/MCM-41/PA/Ni. This composite has fantastic properties like high stability, excellent magnetic performance, and remarkable catalytic activity. The catalyst was characterized by different analyses This MCM-41 silica is like a protective layer around the magnetite particles. This coating process gives the particles some interesting properties. This composite consisted of a mesoporous structure with a surface area of 342.9 m2/g, mean pore size of 5.57 nm, and pore volume of 0.4772 cm3 /g. This unique combination of CoFe2O4 nanoparticles with MCM-41 and PA supports, decorated with Ni creates some outstanding reaction that leads to exceptional performance in synthesizing 5-substituted 1H tetrazoles. This catalyst was recovered and reused several times without significantly decreasing efficiency and stability. [ABSTRACT FROM AUTHOR]

The reactivity of imidazole, pyrazole, 1,2,4‐triazole, 1,2,3‐triazole, and tetrazole with acetone (propan‐2‐one) has been studied by 1H and 13C NMR using acetone‐d6 as solvent at temperatures ranging from 173 to 300 K at 10 K intervals. Simultaneously, the reaction has been theoretically calculated at the B3LYP/6‐311++G(d,p) level, and experimental and theoretical results have been compared. The equilibrium constants between azoles and adducts α,α‐dimethyl‐azole‐methanol were analyzed, assuming that the straight part of the plots –R ln Ke vs. 1/T can be used to determine ΔH and ΔS. Calculated and experimental data are related, but the theoretical values are proportionally higher. The tautomerism of triazoles and tetrazole has been considered in order to discuss the reactions. [ABSTRACT FROM AUTHOR]

Objective: The synthesis, antibacterial, and antioxidant assessment of novel tetrazole derivatives with the 2-amino-5-(4-nitrophenyl)-1,3,4-thiadiazole moiety are the main objectives of this work. Methods: A multi-step procedure was used to synthesis the desired compounds, beginning with the creation of the thiadiazole core and ending with the functionalization of tetrazole rings. Results and Discussion: 2-Amino-5-(p-nitro phenyl)-1,3,4thiadiazole (I) was prepared by reacting p-nitro benzoic acid with thiosemicarbazide in the presence of POCl3. Compound (I) then underwent a reaction with 2-chloroacetohydrazide to produce 2-(5-(4-nitrophenyl)-1,3,4thiadiazol-2-yl)acetohydrazide (II). Several new Schiff bases (IIIa–IIId) were synthesized by reacting compound (I) with different aromatic aldehydes. In contrast, tetrazole derivatives (IVa–IVd) were produced by reacting Schiff bases derivatives (IIIa–IIId) with sodium azide. NMR and infrared spectroscopy were among the spectroscopic methods used to confirm the structures of the produced compounds. Using standard disc diffusion and broth dilution techniques, the antibacterial activity of these derivatives was evaluated against a panel of Gram-positive and Gram-negative bacteria. Additionally, radical scavenging assays was used to assess the antioxidant potential. The results showed that a number of the produced tetrazole derivatives have notable antioxidant and antibacterial properties. Conclusions: These results imply that 2-amino-5-(4-nitrophenyl)-1,3,4-thiadiazole scaffold-containing tetrazole derivatives may be good candidates for the synthesis of novel medicinal medicines with combined antioxidant and antibacterial capabilities. [ABSTRACT FROM AUTHOR]

The chemistry of condensed heterocyclic molecules in terms of their diverse biological properties and role in drug development has been the subject of numerous publications. Tetrazole is a naturally occurring chemical that has been used to create several commercially available drugs and as a result, plays an important role in pharmaceutical chemistry. The current study aimed to create and synthesize seven new 2,5-disubstituted-tetrazole-acetamide derivatives 3a-3g via an N-alkylation reaction of 5-(4-bromophenyl)-2H-tetrazole or 5-(4-chlorophenyl)-2H-tetrazole 1a,1b, and N-acetamide derivatives 2a-2f, and 2g in CH3CN using potassium carbonate as a base in good yields. New molecules were assigned based on nuclear magnetic resonance results (¹H, 13C NMR, and two-dimensional-NMR [heteronuclear single quantum coherence spectroscopy [HSQC]), along with mass spectrometry (EI-MS) techniques. The products' biological activities were confirmed using the tetrazolium (MTT) assay against MCF-7 (breast cancer) and PC3 (prostate cancer) cells and their effects on the normal hepatic cell line, WRL68. Results showed that compounds 3e-3g inhibited PC3 cells with average IC50 values of 32.59, 54.99, and 55.53 μM, respectively. Compounds 3a and 3b demonstrated cytotoxicity against the MCF-7 cell line, with average IC50 values of 94.25 and 68.16 μM, respectively. Compounds 3a, 3c, and 3e-3g on the 3ERT and 3ZK6 receptors demonstrated strong binding capabilities and improved protein interactions according to molecular docking experiments. [ABSTRACT FROM AUTHOR]

The tetrazole moiety remains one of the most interesting scaffolds in the development of new high-energy density materials (HEDMs) because of its desired characteristics, such as high nitrogen content and heat of formation (HOF). The combination of several heterocycles with high HOF seems to be a promising strategy for obtaining energetic materials with superior properties. Herein, we report the synthesis and characterization of a tetrazole polymer, polymethylenetetrazole (PMT), as a potential HEDM. The compound was characterized using NMR, IR, and Raman spectroscopy. Its weight average molecular mass was obtained by static light scattering (SLS), and its physical properties by powder XRD analysis. The density, sensitivity to friction (FS), and impact (IS) of the compound were determined as well. The results of the thermal and energetic properties of PMT suggest that this polymer could be an insensitive explosive. [ABSTRACT FROM AUTHOR]

An efficient palladium‐catalyzed three‐component reaction for the synthesis of tricyclic fused 1,2,3‐triazole derivatives from amino‐NH‐1,2,3‐triazoles, isocyanide and iodoarenes has been developed, involving three new bonds formation by one manipulation in moderate to good yields with excellent functional group tolerance. Moreover, it is also suitable for other N‐heterocyclic substrates including pyrazole, imidazole, indole, tetrazole and its derivatives. [ABSTRACT FROM AUTHOR]

Starting from two different cyano‐functionalized organoboranes, we demonstrate that 1,3‐dipolar [3+2] azide‐nitrile cycloaddition can serve to generate libraries of alkyl‐tetrazole‐functionalized compounds capable of intramolecular N→B‐Lewis adduct formation. Due to the relatively low basicity of tetrazoles, structures can be generated that exhibit weak and labile N→B‐coordination. The reaction furnishes 1‐ and 2‐alkylated regio‐isomers that exhibit different effective Lewis‐acidities at the boron centers, and vary in their optical absorption and fluorescence properties. Indeed, we identified derivatives capable of selectively binding cyanide over fluoride, as confirmed by 11B NMR. This finding demonstrates the potentialities of this synthetic strategy to systematically fine‐tune the properties of lead structures that are of interest as chemical sensors. [ABSTRACT FROM AUTHOR]

This study focused on the synthesis of a variety of Schiff bases and their corresponding tetrazole derivatives. The Schiff bases were prepared by reacting quinaldic acid hydrazide with different aromatic aldehydes, followed by cyclization with sodium azide to form tetrazoles. The structures of the synthesized compounds were confirmed using spectroscopic techniques including FT-IR, XRD, FESEM, and ¹H and 13C-NMR. Thinlayer chromatography (TLC) was utilized to verify the purity of the compounds. The biological properties of the synthesized compounds were investigated against two bacterial species (Staphylococcus epidermidis and Escherichia coli) and a fungal species (Candida albicans). Furthermore, blind molecular docking studies were performed to identify potential binding sites of these compounds within bacterial and fungal receptors. The antioxidant properties of several compounds were also examined, demonstrating antioxidant activity in some of the selected compounds. The results indicated that the synthesized tetrazole derivatives have significant biological and antioxidant activities, making them potential candidates for further pharmaceutical development. [ABSTRACT FROM AUTHOR]

In the context of ongoing research, an efficient single-step multicomponent reaction synthesis for new tetrazole scaffolds has been developed. The Ugi multicomponent process is one of the most promising approaches for the connection of four separate components in a single phase and finds immense application in drug discovery. In this study, tetrazoles were synthesized using the Ugi-Multi Component technique, which involved the condensation of isocyanides, TMS-N3, different aryl amines, aromatic aldehydes with active pharmacophores. Final products were characterized by various spectroscopic techniques viz. IR, NMR, and Mass spectrometry. Tetrazole derivatives were screened for their anticancer activity against the NCI-60 cell lines grouped in 9 different subpanels among which compounds 5b and 5e have been found to be more potent against different cell lines. In order to get mechanistic insights into this antitumor activity, molecular docking analysis against critical target CDK2 was performed. The results of binding affinity were in harmony with the anticancer activity and could provide valuable insights into the various thermodynamic interactions governing the binding affinity. [ABSTRACT FROM AUTHOR]

The present work concentrates on synthesizing and adsorption surface investigation of polytetrazole polymer (P-T) created from polyimine (P-S) grafted with sulfadiazine drug. The prepared polymer is synthesized by mechanochemical polycondensation reaction between dialdehyde aromatic compound and diamine aromatic compound by applying appropriate polar solvent and glacial acetic acid at (78 °C) as dependent on the polymerization reaction. The synthetic route to prepare tetrazole polymer (P-T) consists off multi chemical reaction process, firstly the synthesis of polyimine backbone (P-S) (4-(((4'-amino-3,3'-dimethyl-[1,1'-biphenyl]-4- yl)imino)methyl)benzaldehyde) by Schiff base reaction between monomers diamine (o-tolidine) and dialdehyde (terephthalaldehyde). Secondly, is the sulfadiazine azid formation, since the conversion of sulfadiazine drug to sulfadiazine azid (4-azido-N-(pyrimidin-2-yl)benzenesulfonamide) occurred by diazonium salt formation of sulfadiazine at very low temperature (0–5 °C) and then reaction with sodium azide (NaN3) under cool conditions to convert amine group (NH2) to azide group (N3), after that sulfadiazine azide was grafted onto the polyimine backbone (P-S) by cyclization reaction process to form polytetrazole (P-T). All prepared products: sulfadiazine azide, polyimine (P-S) and polytetrazole (P-T) were characterized by FT-IR spectroscopy. Finally, the adsorption surface investigations of the prepared polymers (P-S) and (P-T) were studied for adsorption of Brilliant cresyl blue (BCB) dye. All adsorption results were recorded by using an UV-Vis spectrophotometer. Since the polytetrazole (P-T) gave very good adsorption results when applied to (BCB) dye adsorption, there can be suggestion on the polytertazole polymer applicability in many various environmental and medical applications. [ABSTRACT FROM AUTHOR]

[Display omitted] A series of new 1 'H -tetrazolo[1 ' ,5 ' - c ]-fused 3-aza-A- homosteroids were synthesized by azidation of progesterone, testosterone and hydrocortisone acetate in the presence of silicon tetrachloride. According to NMR spectroscopy and X-ray analysis, two double bond positional isomers (double bond in ring A or in ring B) are formed in various ratios; according to quantum chemical calculations, their energies are close within 0.4 kcal mol-1. Only low cytotoxic activity against Hep-2, MCF-7, HepG2, and Hek293 cell lines was determined in vitro for the compounds obtained. [ABSTRACT FROM AUTHOR]

A new series of tetrazole fused with 1,3,4‐thiadiazole‐2‐amine (4a–j) moiety have been synthesized. A thorough characterization of each compound was carried out using mass spectrum data, FT‐IR, 1H, and 13C NMR studies. The antibacterial effectiveness of these prepared substances was assessed in vitro against Gram‐(−) strains of P. aeruginosa and E. coli, as well as Gram‐(+) strains of B. subtilis and S. aureus. Molecules 4f and 4h showed exceptional effectiveness against both types of strains when compared to the reference antibiotic Streptomycin. Moreover the evolution of the molecular docking (in silico) studies also helpful for all the synthesized compounds and reference amoxicillin. The investigation included a look at protein stability, APO‐protein dynamics, and interactions. Using Molecular Dynamics (MD) simulations with Desmond Maestro version 11.3 for this inquiry, a potential lead molecule was found. [ABSTRACT FROM AUTHOR]

An efficient, mild, and regioselective synthesis of substituted 1‐methyl‐1H‐tetrazole using methyl 2,2,2‐trichloroacetimidate is described. The substrate scope of the methodology has been established with wide variety of tetrazoles. N1‐Methylated tetrazoles were synthesized with high yields (85%–97%). [ABSTRACT FROM AUTHOR]

Non-annulated tetrazole-containing polynuclear compounds, in which heterocyclic fragments are bound by an acetamide linker were synthesized. The synthesis was accomplished by acylation of 2-hydrazinyl-4,6-dimethylpyrimidine, 4-amino-4H-1,2,4-triazol-3-thiol, 2-[(1-amino-1H-tetrazol-5-yl)thio]-N-tert-butylacetamide, 1-methyl-1H-tetrazol-5-amine, and 2-methyl-2H-tetrazol-5-amine with one key reagent, (5-phenyltetrazol-2-yl)acetyl chloride. Preliminary in silico studies showed the presence of the in vivo antidiabetic (diabetes 2 type) activity in N′-(4,6-dimethylpyrimidin-2-yl)-2-(5-phenyl-2H-tetrazol-2-yl)acetohydrazide. N-(3-Mercapto-4H-1,2,4-triazol-4-yl)-2-(5-phenyl-2H-tetrazol-2-yl)acetamide demonstrated minimal hypoglycemic activity in in vivo studies, at the same time, it showed pronounced activity as a drug for combating obesity. [ABSTRACT FROM AUTHOR]

As the grade of the copper concentrate decreases and its composition becomes increasingly complex, the silver content in anode plates cast after fire refining increases, leading to a higher silver content in the copper cathode during electrorefining and a substantial loss of precious metals. This study investigates the impact of 5-amino-1H tetrazole (5-AT) on reducing silver in copper cathodes during electrorefining with high silver content anode plates. 5-AT forms an "adsorption layer" on the anode surface, reacting with Ag+ released by the anode to form a precipitate and prevent Ag+ from entering the electrolyte. This process agglomerates fine Ag-Se compounds and AgCl particles, creating larger anode slime particles that settle quickly, thus inhibiting fine silver-containing particles from adhering to the cathode. Furthermore, 5-AT adsorbs on the cathode, binding with Cu+ and promoting the Cu2+ electrodeposition process while inhibiting Ag+ electrodeposition. This facilitates uniform copper cathode grain growth and reduces inclusions in the copper cathode. The grain size of the copper cathode initially decreases and then increases as the concentration of 5-AT increases. At an optimal 5-AT concentration of 15 mg/L, the Ag content in the copper cathode decreased from 6.9 ppm to 4.7 ppm, indicating the potential efficacy of 5-AT in improving the quality of electrorefined copper. [ABSTRACT FROM AUTHOR]

Polycyclic indoles are prevailed in natural products, pharmaceuticals and biologically active compounds. Herein is described photo‐induced difluoromethylation‐cyclization of N‐alkene tethered indoles to synthesis of tetrahydropyrido[1,2‐a]indole using 5‐((difluoromethyl)sulfonyl)‐1‐phenyl‐1H‐tetrazole as a CF2H radical source. This photochemical reaction tolerates an array of functional groups like ester, cyano, ketone, halide, ether, aldehyde and heteocycles. Mechanistic experiments indicated that the difluoromethyl radical and the single electron transfer were involved. [ABSTRACT FROM AUTHOR]

The late‐stage functionalization of active pharmaceutical ingredients is a key challenge in medicinal chemistry. Furthermore, N‐aryl triazoles and tetrazoles are important structural motifs with the potential to boost the activity of diverse drug molecules. Using easily accessible dibenzothiophenium salts for the ruthenium‐catalyzed C−H arylation, these scaffolds were introduced into a variety of bioactive compounds. Our methodology uses cost‐efficient ruthenium, KOAc as a mild base and gives access to a plethora of highly decorated triazole and tetrazole containing drug derivatives. [ABSTRACT FROM AUTHOR]

A series of Tetrazole derivatives containing pyrrole‐2,5‐dione groups (5 a–e) were synthesized and comprehensively characterized using HRMS, FT‐IR, and 1H−, 13C‐NMR spectroscopic techniques. These compounds were evaluated for their ability to inhibit urease activity in vitro, demonstrating remarkable inhibitory potential with IC50 values ranging from 4.325±1 to 18.28±1 μM, surpassing the standard thiourea (IC50=17.386±1 μM). Notably, compounds 5 b (IC50=4.325±1 μM), 5 e (IC50=7.411±1 μM), 5 c (IC50=9.313±1 μM), and 5 a (IC50=10.46±1 μM) exhibited notably higher activity compared to the standard thiourea. In our exploration of the structure‐activity relationship (SAR), we investigated the impact of differently substituted aryl rings on inhibitory potential. Our results highlight the crucial role of substituent positioning on the aryl ring, independent of the nature of the substituents. Additionally, computational studies were conducted on all compounds, supporting our experimental findings. Molecular docking simulations revealed a strong correlation between biological evaluation results and computational predictions, affirming the promising inhibitory activity of the compounds. [ABSTRACT FROM AUTHOR]

This article explores the synthesis and analysis of a zwitterionic compound called (5-Iminio-4,5-dihydro-1,3,4-oxadiazol-2-yl)tetrazol-1-ide, which is a promising energetic material. The article discusses the importance of developing high energy performance and low mechanical sensitivity in energetic materials for weapons advancement. It also explores the use of tetrazole in green explosives and the incorporation of 1,3,4-oxadiazole and amino groups to improve safety. The article concludes with a discussion of the synthesis and analysis of the zwitterionic compound, highlighting its low mechanical sensitivity and favorable thermal stability. Safety precautions are emphasized when working with these materials. [Extracted from the article]

This article explores the generation of alkylidene carbenes through tetrazole fragmentation and their applications in organic synthesis. It discusses different methods for generating alkylidene carbenes, such as the loss of N2 from 1-diazoalkenes and the fragmentation of tetrazole intermediates. The text also discusses the synthesis of heteroatom-substituted alkynes (HATs) and heterocyclic alkynes (HATs) using various methods and their potential applications in the synthesis of biologically active natural products. The article highlights the versatility and efficiency of the cyclopropane (CP) method for compound synthesis and provides detailed examples and reactions to illustrate its effectiveness. [Extracted from the article]

[Display omitted] • Rare [Cu 4 I 2 ]2+ cationic cluster constructs a novel 3D Cu(I)-MOF. • The stable Cu(I)-MOF shows sensitive detection ability for ROX, NFZ and NFT. • Hierarchical porous Cu(I)-MOF/MF composites were built by a one-pot method. • The Cu(I)-MOF/MF exhibits remarkable adsorption capacity towards ROX, NFZ and NFT. Fluorescence quenching induced by photoinduced electron transfer (PET) stands as an effective strategy for identifying water pollutants. Herein, a novel (4, 8)-connected three-dimensional framework Cu(I)-MOF ([Cu 2 I(tpt)] n) with unique 8-connected [Cu 4 I 2 ]2+ cationic clusters is designed by employing the nitrogen-rich ligand (Htpt = 5-[4(1 H -1,2,4-triazol-1-yl)]phenyl-2 H -tetrazole). Water-stabilized Cu(I)-MOF exhibits outstanding fluorescence properties, facilitating its application in detecting organic pollutants in water. Benefiting from the fact that the Cu(I)-MOF possesses a higher lowest unoccupied molecular orbitals (LUMO) energy level than that of the analyte, the rapid d-PET can occur, entitling Cu(I)-MOF to a sensitive fluorescence quenching response to roxarsone (ROX), nitrofurazone (NFZ) and nitrofurantoin (NFT) (with detection limits as low as 0.13 µM, 0.15 µM, and 0.13 µM, respectively). The nitrogen-containing sites of melamine foam (MF) are utilized to facilitate the anchoring and growth of Cu-MOF crystals, which enables the preparation of hierarchical microporous − macroporous Cu(I)-MOF/MF composites. The ordered porous structure of Cu(I)-MOF/MF provides cavities and open sites for the efficient removal of ROX (q max = 210.6 mg∙g−1), NFZ (q max = 111.5 mg∙g−1) and NFT (q max = 238.9 mg∙g−1) from water. This characteristic endows the Cu(I)-MOF/MF with rapid and recyclable adsorption capacity. Therefore, this work provides valuable insights to address the problem of detection and removal of pollutants in the aquatic environment. [ABSTRACT FROM AUTHOR]

Over the past 20 years, there has been a notable rise in the incidence of invasive bacterial infections. This increase has been mostly linked to the growth of drug‐resistant bacteria. Tetrazoles have been considered as promising antibacterial agents and their effectiveness may be enhanced by hybridization with other antibacterial pharmacophores. In this work, a series of tetrazole hybrids (1‐6) containing oxazepane and pyrazole rings as well as Mannich bases (7,8) were synthesized via the Schiff and Mannich reactions, respectively. The compositions were proven spectroscopically using infrared spectra, proton (1H) and carbon‐13 (13C) nuclear magnetic resonance spectra and elemental analyses. Moreover, the pharmacokinetic properties viz Absorption, Distribution, Metabolism and Excretion (ADME) were predicted in silico using SwissADME server. Compounds 1,2 and 4–6 attaining the best drug‐likeness properties were screened for their antibacterial activities against Staphylococcus epidermidis and Streptococcus mutans at different concentrations in comparison with tetracycline and amikacin, respectively. Afterwards, a molecular docking study was performed to explore the potential binding patterns of the new antibacterial compounds. Collectively, the tetrazole hybrids 4 and 5 have been found to have higher inhibitory potencies compared to tetracycline, serving them as potential antibacterial candidates which can be further optimized in the future. [ABSTRACT FROM AUTHOR]

1,2,4‐triazolo‐[4,3‐a]pyrazine was prepared via a two‐step electrochemical, photochemical process. First, a 5‐substituted tetrazole is electrochemically coupled to 2,6‐dimethoxypyrazine to yield 1,5‐ and 2,5‐ disubstituted tetrazoles. Subsequent photochemical excitation of the 2,5‐disubstituted tetrazole species using an ultraviolet lamp releases nitrogen gas and produces a short‐lived nitrilimine intermediate. Subsequent cyclization of the nitrilimine intermediate yields a 1,2,4‐triazolo‐[4,3‐a]pyrazine backbone. The scope of this reaction was explored using various tetrazoles and pyrazines. Materials produced were identified using chemical analytical techniques and computationally studied for potential application as an insensitive energetic material. [ABSTRACT FROM AUTHOR]

Multicomponent diversity–oriented synthesis (DOS) of conformationally anchored structural peptidomimetics like 2,5‐diketopiperazines (2,5‐DKP) containing heterocyclic bioisosteres of the amide bond, such as 1,2,3‐triazoles and 1,5‐disubstituted tetrazoles (1,5‐DS−T) is described. Structural peptidomimetics are synthesized from similar available starting materials, via a strategy based on isocyanide‐based multicomponent reactions (IMCRs): Ugi‐4CR and Ugi‐Azide (UA), followed by a one‐pot process: SN2/intramolecular alkyne‐azide cycloaddition (IAAC). The sequential aligning of two powerful synthetic tools (IMCR and IAAC) has parallelly contributed to generate anchored conformation and complexity in target molecules, which are considered structural peptidomimetics of 2,5‐DKP. Herein, the 1,2,3‐triazole ring plays a key role in the preference for the boat conformation. Furthermore, the use of UA reaction generates scaffold diversity at the N‐1 α‐carbon of the pyrazinone ring, replacing a linear amide bond with a heterocyclic bioisostere such as 1,5‐DS−T leading to the synthesis of novel tricyclic peptidomimetics. The DFT calculations confirmed the boat conformation of the synthesized molecules. [ABSTRACT FROM AUTHOR]

As a hybrid weapon, two novel series of pyrazoles, 16a‐f and 17a‐f, targeting both COX‐2 and ACE‐1‐N‐domain, were created and their anti‐inflammatory, anti‐hypertensive, and anti‐fibrotic properties were evaluated. In vitro, 17b and 17f showed COX‐2 selectivity (SI = 534.22 and 491.90, respectively) compared to celecoxib (SI = 326.66) and NF‐κB (IC50 1.87 and 2.03 μM, respectively). 17b (IC50 0.078 μM) and 17 f (IC50 0.094 μM) inhibited ACE‐1 comparable to perindopril (PER) (IC50 0.048 μM). In vivo, 17b decreased systolic blood pressure by 18.6%, 17b and 17f increased serum NO levels by 345.8%, and 183.2%, respectively, increased eNOS expression by 0.97 and 0.52 folds, respectively and reduced NF‐κB‐p65 and P38‐MAPK expression by −0.62, −0.22, −0.53, and −0.24 folds, respectively compared to l‐NAME (−0.34, −0.45 folds decline in NF‐κB‐p65 and P38‐MAPK, respectively). 17b reduced ANG‐II expression which significantly reversed the cardiac histological changes induced by L‐NAME. [ABSTRACT FROM AUTHOR]

Organic azides are universally important in many areas of chemistry, particularly in organic synthesis. The availability of these azides often depends on specific transfer reagents and reaction conditions, or only work with certain substrates. Customizable transfer reagents offer a safe and direct pathway to desired compounds, thereby increasing the availability of N‐alkyl‐azides. In an effort to streamline the synthesis and broaden the scope of N‐azidoethyl‐containing molecules, three different versatile azidoethyl transfer reagents were synthesized and a uniform reaction protocol with azoles as substrates, including imidazole, pyrazole, 1,2,3‐triazole, 1,2,4‐triazole, and tetrazole was established. The resulting azidoethyl‐azoles were further used as ligands for energetic coordination compounds in an effort to create new lead‐free primary explosives. A comprehensive characterization of the transfer reagents, the azidoethyl‐containing products, and energetic coordination compounds was conducted using multinuclear nuclear magnetic resonance (NMR), elemental analysis, mass spectrometry, and infrared spectroscopy (IR). Furthermore, their thermal stability and sensitivity toward friction and impact were determined as well as the detonation properties were calculated by using the EXPLO5 code. [ABSTRACT FROM AUTHOR]

Synthesis of 5-substituted-1H-tetrazole derivatives from aryl aldehydes under the influence of Palladium nanoparticles entrapped in aluminum hydroxide matrix (Pd/AlO(OH) NPs) was carried out in ethanol for 3-6 h. The use of the catalyst in this synthesis is the first. Sodium azide and malononitrile used in the reaction are chemical compounds required in the synthesis of tetrazoles. The reactions were concluded with good yields under thermal conditions. In the reactions, twelve derivatives were synthesized. The synthesized compounds were characterized by IR, 1H, and 13C NMR. The olefinic proton's signal, which is around 8.5 ppm, reveals the formation of the tetrazole ring. The tyrosinase enzyme activity for each synthesized derivative was examined, and the results were recorded. According to the results obtained, all tetrazole derivatives were found to be effective compounds for tyrosinase enzyme inhibition. 3-(3,4-dichlorophenyl)-2-(1H-tetrazol-5-yl)acrylonitrile (2k) with two chloride groups at the meta and para position of the phenyl ring seems to be the most potent tyrosinase inhibitor with an IC50 value of 45 µM. [ABSTRACT FROM AUTHOR]

Various types of materials have been explored in the pursuit of high energy density materials (HEDMs) that have balanced energy and stability. Among them, energetic salts show numerous advantages, such as lower vapor pressures, high physical stabilities, and the opportunity for favorable tuning by careful selection of cations/anions. Nitrogen-rich bases are generally used as cations for energetic salt formation. While the synthesis of salts with larger cations lowers the sensitivity, smaller cations aid better energetic performance. A combination of both in the same ionic moieties might help in the formation of a superior explosive. In this work, a facile route for the synthesis of mixed dicationic energetic salts based on 1-((1H-tetrazol-5-yl)methyl)-3,5-dinitro-1H-pyrazol-4-ol (compound 1) has been explored by various combinations of bigger and smaller cations (compounds 4-10). All the synthesized energetic salts showed high positive heats of formation, energetic performance comparable to TATB, excellent stability towards impact and friction, and acceptable thermal stabilities. This improved technique will provide an additional option for fine-tuning the energetic properties of HEDMs and will facilitate in exploring the role of various cations in the overall performance of the energetic compounds. [ABSTRACT FROM AUTHOR]

This review focuses on the latest advancements in combustible components of solid rocket fuel and explores the potential use of hydrides, nitriles, and tetrazoles as its components. [ABSTRACT FROM AUTHOR]

We present the synthesis and characterization of a new Cu(I) complex supported on SBA‐15 as a catalyst for preparing anilines from the reaction of aryl halides with sodium azide. The SBA‐15 support was modified by treating it sequentially with (3‐aminopropyl) triethoxysilane (APTES), cyanuric chloride, and 2‐aminothiazole (AT). The modified mesoporous silica, SBA‐15@BAT, was then treated with a CuI solution in acetonitrile to give SBA‐15@BAT‐Cu(I). The catalyst underwent thorough characterization using conventional methods. X‐Ray photoelectron spectroscopy (XPS) analysis corroborated the presence of copper in the +1 oxidation state in the catalyst. The supported Cu(I) complex sufficiently catalyzed the amination reaction of iodo‐, bromo‐, and chloroarenes with NaN3. The catalyst was centrifuged, washed, and applied in the subsequent run. We investigated the effects of various reaction components and parameters to determine the optimal conditions for the reaction. The heterogeneous catalyst exhibited noticeable stability and was reused over seven runs with slight deactivation. [ABSTRACT FROM AUTHOR]

Easy operation, readily accessible starting materials, and direct synthesis of iminotetrazoles via metal‐free aerobic oxidation were achieved in one‐pot Ugi‐azide multicomponent reactions. A study of the reactivity of 2‐hydroxybenzaldehyde (Salicylaldehyde) as single reactant replacement (SSR) in classical Ugi reaction has been carried out showing an outcome that differs by simply varying the ortho‐substituents of the benzaldehyde moiety. In doing so, various substituted imino tetrazole products could be obtained directly in one step by simple execution without oxidation step in good yields. Characterization of these new iminotetrazole products was confirmed by X‐ray analysis. [ABSTRACT FROM AUTHOR]

Metal–organic self-assembly with flexible moieties is a budding field of research due to the possibility of the formation of unique architectures. Tetrazole, characterised by four nitrogen atoms in a five-member ring, exhibits immense potential as a component. Tetrazole offers four coordination sites for binding to the metal centre with nine distinct binding modes, leading to various assemblies. This review highlights different polymeric and discrete tetrazole-based assemblies and their functions. The meticulous manipulation of stoichiometry, ligands, and metal ions required for constructing discrete assemblies has also been discussed. The different applications of these architectures in separation, catalysis and detection have also been accentuated. The latter section of the review consolidates tetrazole-based cage composites, highlighting their applications in cell imaging and photocatalytic applications. [ABSTRACT FROM AUTHOR]

Herein, we report a solvent-free and sustainable methodology for the electrophilic C–H thiocyanation of indoles and imidazo[1,2-a]pyridines in a mixer-mill. A combination of commercially available and cheaper precursors N-chlorosuccinimide and NaSCN was used under milling conditions for the in situ generation of N-thiocyanatosuccinimide (NTS) which facilitates the C-3 selective thiocyanation reaction on indoles and imidazo[1,2-a]pyridines. A series of thiocyanated products containing electron-rich and electron-deficient rings were synthesized in silica gel as the solid reaction media and good to excellent yields were obtained. The scalability of the reaction was validated with selected substrates at the gram scale. Moreover, we explored mechanochemical tandem C–C and C–S bond formation reactions by double C–H activation, leading to easy access to C-2 aryl and C-3 thiocyanato compounds from unsubstituted indoles. In addition, mechanochemical conversion of the –SCN precursors into –SCF3 and 5-substituted sulfenyl tetrazole was also demonstrated in the current methodology. [ABSTRACT FROM AUTHOR]

AbstractA reusable and efficient double shell hollow CuO microsphere was synthesized by hydrothermal method. Various techniques such as X-ray diffraction (XRD), transmission electron microscopy (TEM), field emission scanning electron microscopy (FESEM), elemental mapping and BET have been used for characterization of catalyst. The catalyst was used as an efficient and safe catalyst in the [3 + 2] cycloaddition reaction of organic nitriles with sodium azide in PEG 200 as a green solvent under mild condition. A variety of aromatic commercial and non-aromatic synthesized nitriles was used to produce the corresponding tetrazoles in good to excellent yields. The recovery and reusability of catalyst was also investigated. The catalyst was recovered by simple filtration and reused five times. After five recycles, the catalyst still showed a significant activity and gave the desired product in fairly good yield. [ABSTRACT FROM AUTHOR]