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The asymmetric unit of the title compound, C25H19N5O3, is composed of two independent molecules with slightly different conformations. The extended structure features N—H...O hydrogen bonds as well as π–π interactions.

Unexpected ring closure of 2-(1-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazole-4-carbonyl)-N-phenylhydrazine-1-carbothioamide (3) on exposure to sulfuric acid at room temperature for an extended duration (12 h) gave 4-((5-(1-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl)-1,3,4-thiadiazol-2-yl)amino)benzenesulfonic acid (4) in 75% yield. The use of sulfuric acid led to sulfonation at the para-position of the benzene ring in phenyl isothiocyanate. The crystal structure comprises two independent types of molecules of 4 and two disordered ether solvent molecules. The synthesized benzenesulfonic acid inhibits the growth of both Listeria monocytogenes and Escherichia coli and its activity was comparable to those obtained for ampicillin and vancomycin.

Reactions of 1-(5-methyl)-1H-1,2,3-triazol-4-yl)ethan-1-ones and benzaldehydes in ethanol under basic conditions gave the corresponding chalcones. Reactions of the chalcones combined with thiosemicarbazide in dry ethanol containing sodium hydroxide afforded the corresponding pyrazolin-N-thioamides. Reactions of the synthesized pyrazolin-N-thioamides and several ketones (namely, ethyl 2-chloro-3-oxobutanoate, 2-bromoacetylbenzofuran, and hydrazonoyl chloride) gave the corresponding novel 2-(1,2,3-triazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)thiazoles in high yields (77–90%). Additionally, 2-(4,5-dihydro-1H-pyrazol-1-yl)-4-(1H-1,2,3-triazol-4-yl)thiazoles were obtained in high yields (84–87%) from reactions with N-pyrazoline-thioamides and 4-bromoacetyl-1,2,3-triazoles under basic conditions. The structures of six of the newly synthesized heterocycles were confirmed by X-ray crystallography.

Reactions of 1-(5-methyl)-1

A new series of 1,4,5-trisubstituted triazole-bearing benzenesulphonamide moiety, COX-2 pharmacophore, was designed and synthesized. The synthetic pathway for preparation of the new 1,2,3-triazole derivatives started with the preparation of the two key intermediates: 4-(4-acetyl-5-methyl-1H-1,2,3-triazol-1-yl)benzenesulfonamide 3 and 4-(4-(hydrazinecarbonyl)-5-methyl-1H-1,2,3-triazol-1-yl)benzenesulfonamide 13 that were then used to synthesize the new triheterocycles. All the synthesized compounds were virtually screened for their binding interactions with both COX isozymes. Compounds showing similar conformation to that of celecoxib, the co-crystallized ligand, and exhibited reasonable interactions, were then evaluated for their in vitro COX-1 and COX-2 inhibition activity. All the compounds under investigation were found to be active as COX-1 and COX-2 inhibitors. Compounds 11 and 13 showed the highest activity as COX-2 inhibitors with IC50 values of 2.618 and 2.92 µM, respectively. On the other hand, compound 13 showed moderate selectivity toward COX-2 inhibition with selectivity ratio of 6.99. Summing up, as confirmed by in vitro and in silico results, the triazolyl benzenesulfonamide derivative 13-bearing unsubstituted hydrazide moiety can be considered as suitable candidate for further investigation as selective COX-2 inhibitor.

2-Cyano-3-(1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl)acrylamide (3) was synthesized in 90% yield from condensation of equimolar equivalents of 1-phenyl-3-(thiophen-2-yl)-1H-pyrazole-4-carbaldehyde (1) and 2-cyanoacetamide (2) in boiling ethanol under basic condition for 45 min. The structure of 3 was determined using NMR spectroscopy and single crystal X-ray diffraction.

The reaction of pyrazole-3-carbohydrazide (1) or 1,2,3-triazole-4-carbohydrazides 5a,b and 2-(ethoxymethylene)malononitrile (2) in ethanol under reflux conditions afforded the corresponding N,N'-diacylhydrazines 3 or 6a,b, respectively in high yields. Ring closure of 3 or 6a,b in the presence of phosphorus oxychloride furnished the corresponding 2,5-bis(heterocyclic)-1,3,4-oxadiazoles 4 or 7a,b, respectively in good yields. The synthesized heterocyclic compounds showed moderate activity against Staphylococcus aureus, Listeria monocytogenes, and Escherichia coli.

Four 2-(2-(5-(4-Methoxyphenyl)-1-phenyl-1H-pyrazole-3-carbonyl) hydrazono)-N’-arylpropanehydrazonoyl chlorides were designed outset from 4-methoxyaceteophenone, as raw matter, by interacting of carbohydrazide with four hydrazonoyl chloride derivatives in refluxing ethanol. The synthesized heterocycles stone was depicted and utilized through simple concern finishing as azo dyes for coloring and functionalization of cotton fabric. The outcomes obtained disclosed that the finishing treatments improved the nitrogen percent as well as wrinkle recovery angles along with a modicum decreasing in the tensile strength of treated fabric samples compared with the untreated fabric. The results assured also the perfect color fastness properties of the dyed samples, irrespective of the dye chemical structure. Besides, such dyes improved the treated fabric antibacterial properties as well as protection against the deleterious sun radiation. After 15 washing cycles, the dyed/finished samples exhibited satisfactory color strength and acceptable functional properties confirming stability and the tight binding of such dyes to the fabric chemical structure. Otherwise, both the untreated and treated textiles were recognized by means of scan electron microscope that signalizes hunting of such dyes by the cotton fabric structure.

The title compound was synthesized and structurally characterized. Theoretical IR, NMR (with the GIAO technique), UV, and nonlinear optical properties (NLO) in four different solvents were calculated for the compound. The calculated HOMO–LUMO energies using time-dependent (TD) DFT revealed that charge transfer occurs within the molecule, and probable transitions in the four solvents were identified. The in silico absorption, distribution, metabolism, and excretion (ADME) analysis was performed in order to determine some physicochemical, lipophilicity, water solubility, pharmacokinetics, drug-likeness, and medicinal properties of the molecule. Finally, molecular docking calculation was performed, and the results were evaluated in detail.

The title compound was synthesized and structurally characterized. Theoretical IR, NMR (with the GIAO technique), UV, and nonlinear optical properties (NLO) in four different solvents were calculated for the compound. The calculated HOMO-LUMO energies using time-dependent (TD) DFT revealed that charge transfer occurs within the molecule, and probable transitions in the four solvents were identified. The in silico absorption, distribution, metabolism, and excretion (ADME) analysis was performed in order to determine some physicochemical, lipophilicity, water solubility, pharmacokinetics, drug-likeness, and medicinal properties of the molecule. Finally, molecular docking calculation was performed, and the results were evaluated in detail.

It is critical to take safety action if carcinogenic heavy metals and ammonia can be detected quickly, cheaply, and selectively in an environmental sample. As a result, compound 4a [4-(1-(2-(2,4-Dinitrophenyl)hydrazineylidene)-3-(naphthalen-2-yl)allyl)-5-methyl-1-phenyl-1 H-1,2,3-triazole] and compound 4b [4-(1-(2-(2,4-Dinitrophenyl)hydrazineylidene)-3-(naphthalen-2-yl)allyl)-1-(4-fluorophenyl)-5-methyl-1 H-1,2,3-triazole] were prepared. The aldol condensation process of 4-acetyl-1,2,3-triazoles 1a,b (Ar = C6H4; 4-FC6H4) with 2-naphthaldehyde yields 1-acetyl-1,2,3-triazoles 1a,b (Ar = C6H4; 4-FC6H4) (5-methyl-1-aryl-1 H-1,2,3-triazol-4-yl) -3-(naphthalen-2-yl)prop-2-en-1-ones 3a,b with a yield of around 95%. The target compounds 4a,b are obtained in around 88% yield by condensation of 3a,b with (2,4-dinitrophenyl)hydrazine in a refluxing acidic medium. Compounds 4a,b exhibited possible colorimetric detection for chromium ion in the range of 0–14 ppm and ammonia in the range of 0–20 ppm. As a result, this research suggests that strong electron-withdraw groups in related probes can improve anion detection ability, while the conjugation effect should also be considered while building structures.

The reaction of 1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one (1) with excess hydroxylamine hydrochloride (2 mole equivalents) in dry ethanol afforded (E)-1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one oxime (2) in 86% yield. The structure of the new heterocycle 2 was confirmed using nuclear magnetic resonance spectroscopy, single crystal X-ray and elemental analysis.

C30H25FN10S⋅C3H7NO, triclinic, P1̄ (no. 2), a = 10.9189(6) Å, b = 12.3898(7) Å, c = 13.9206(7) Å, α = 199.412(4)°, β = 110.024(5)°, γ = 105.904(5)°, V = 1631.17(17) Å3, Z = 2, R gt(F) = 0.0536, wR ref(F 2) = 0.1471, T = 296 K.

C25H17BrFN3S, triclinic, P1̄ (no. 2), a = 11.2926(6) Å, b = 11.5832(4) Å, c = 16.9974(9) Å, α = 109.211(4)°, β = 90.211(4)°, γ = 95.290(4))°, V = 2089.21(18) Å3, Z = 4, R gt(F) = 0.0580, wR ref(F 2) = 0.1797, T = 296 K.

A reaction of equimolar equivalents of 2-naphthaldehyde (1) and 1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one (2) in ethanolic sodium hydroxide at 20 °C for 4 h gave (E)-1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)-3-(naphthalen-2-yl)prop-2-en-1-one (3) in 92% yield. Nuclear magnetic resonance spectroscopy and single-crystal X-ray diffraction were used to establish the structure of 3.

Reaction of equimolar equivalents of 1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one (1) and N-phenylhydrazinecarbothioamide (2) in boiling ethanol containing a catalytic amount of concentrated hydrochloric acid for 4 h gave (Z)-2-(1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethylidene)-N-phenylhydrazine-1-carbothioamide (3) with 88% yield. The structure of 3 was established using single-crystal X-ray diffraction and magnetic resonance spectroscopy.

4-(4-Chlorophenyl)-2-(5-(4-fluorophenyl)-3-(1-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)thiazole (4) and 4-(4-fluorophenyl)-2-(5-(4-fluorophenyl)-3-(1-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)thiazole (5) have been synthesized in high yields. Crystallization of 4 and 5 from dimethylformamide solvent produced samples suitable for structure determination by single crystal diffraction. The materials are isostructural with triclinic, PĪ and symmetry and comprise two independent molecules in the asymmetric unit. The two independent molecules in the asymmetric unit assume similar conformation. The molecule is essentially planar apart from one of the two fluorophenyl groups, which is oriented roughly perpendicular to the plane of the rest of the molecule.

The complete molecule of the title compound, C16H12Cl4N2O4, is generated by a crystallographic centre of symmetry. In the crystal, N—H...O hydrogen bonds link the molecules into [010] chains featuring R 2 2(10) loops. The chains are cross-linked by short Cl...N contacts [3.224 (2) Å].

C22H10Br4N4O3S, monoclinic, P21/c (no. 14), a = 9.3725(6) Å, b = 20.0436(12) Å, c = 15.3281(11) Å, β = 102.896(6)°, V = 2806.9(3) Å3, Z = 4, R gt (F) = 0.0575, wR ref(F 2) = 0.1566, T = 296 K.

The complete mol-ecule of the title compound, C

The title compound, C

The title compound, C24H20N2O4·H2O, crystallizes with half a molecule of 2-(naphthalen-2-yloxy)-N′-[2-(naphthalen-2-yloxy)acetyl]acetohydrazide and half a water molecule in the asymmetric unit. In the crystal, molecules form planes parallel to (011). Two molecules are connected by water molecules via O—H...O and N—H...O hydrogen bonds.

A reaction of equimolar equivalents of 1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carbohydrazide (1) and indoline-2,3-dione (2) in boiling ethanol for 4 h under acidic conditions gave 1-(4-methoxyphenyl)-5-methyl-N’-(2-oxoindolin-3-ylidene)-1H-1,2,3-triazole-4-carbohydrazide (3) in 88% yield. The structure of 3 was ascertained by NMR spectroscopy and single-crystal X-ray diffraction.

Two new multicomponent crystals consisting of 3,5-bis(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide (1) with 1,3-bis(4-methoxyphenyl)prop-2-en-1-one (2) and with dimethylformamide (DMF), both in 1:1 ratio, prepared and structurally characterized. The occurrence of 1 in different crystal structures enabled a comparison of hydrogen bonding contacts between the two structures as well as with the known structure of pure 1. The backbone of molecule 1 was similar in the structures but the orientation of the methoxy groups varied. Molecule 1 was involved in various combinations of the possible hydrogen bonding contacts, including N–H…O=C, N–H…OMe, and N–H…S. Both N–H hydrogens in the cocrystal (1–2) and the solvate (1-DMF) participated in hydrogen bonding but only one hydrogen atom took part in the structure of pure 1. The S atom accepted contacts in both the structures of pure 1 and cocrystal 1–2 but not in that of the 1-DMF solvate. The oxygen atoms of both methoxy groups acted as acceptors in the structure of pure 1, whereas one oxygen was involved in the 1-DMF solvate and none in cocrystal 1–2.

WOS: 000526086200009 The experimental FT-IR, Ra, NMR, and UV spectral data along with the theoretical quantum chemical calculations for 5-methyl-1-(4-methylphenyl)-N'-[1-(thiophen-2-yl)ethylidene]-1H-1,2,3-triazole-4-carbohydrazide were investigated in detail. For the theoretical computations, the DET/B3LYP functional and 6-311++G(d,p) basis set was used in the ground state and the assignments of harmonic vibrational wavenumbers were carried out using potential energy distribution (PED) based on the use of the VEDA4 software. Additionally, the analyses of the Hirshfeld surface, frontier molecular orbital (HOMO-LUMO), UV based on the IEFPCM solvent model, MEP and NLO were performed for the optimized structure. Finally, the molecular docking between the molecule and protein-PDB:2KCE was investigated using the AutoDock Vina program. The compound was found to be a good potential anticancer due to its binding energy and affinity for protein active sites. (C) 2020 Elsevier B.V. All rights reserved. Deanship of Scientific Research, King Saud UniversityDeanship of Scientific Research at King Saud University The authors are grateful to the Deanship of Scientific Research, King Saud University for funding through Vice Deanship of Scientific Research Chairs.

The mol-ecule of the title compound, C

C27H21N5O, triclinic, P1̄ (no. 2), a = 8.1464(7) Å, b = 10.3861(8) Å, c = 13.2507(9) Å, α = 84.898(6)°, β = 89.413(6)°, γ = 80.351(7)°, V = 1100.88(15) Å3, Z = 2, R gt(F) = 0.0648, wR ref(F 2) = 0.1726, T = 296(2) K.

Investigations in the discovery of tyrosinase enzyme inhibitors have the potential to design novel anti-cancer drugs. A variety of novel bivalent pyrazolinyl triazoles 5–7 were synthesized and identified. The bis-acetyl triazole 3 was accomplished via two-step process first by preparation of diazide 2 followed its coupling reaction with acetylacetone in basic medium. The Claisen–Schmidt condensation reaction of 3 with two moles equivalent of benzaldehyde produces the corresponding bis-α, β-unsaturated ketone 4. Treatment of Schiff base 4 with excess hydrazine hydrate in either acetic acid or ethanol/DMF afforded the bis-N-acetylpyrazline 5 or bis-pyrazoline 6, respectively. Finally, treatment of 6 with two derivatives of isothiocyanate analog gives the bis-N-thioamide pyrazolines 7a and 7b. The synthesized compounds were evaluated as anti-tumor candidates against three human cancer cell lines (MCF-7, HepG2, and HCT-116). The bioscreening evaluation showed that compounds 7a and 6 had a significant antineoplastic potencies (IC50: 32.26 and 57.06 µg/mL) against breast MCF-7 and hepatic HepG2 cancerous cell lines, respectively, in relative to the standard drug, 5-fluorouracil. Molecular docking studies of the synthesized compounds were investigated as VEGFR2 TK inhibitors.

Pyrazolylquinoxalines act as important intermediates for the production of novel derivatives with potential biological applications. The current review covers the synthesis of 2(3)-(pyrazol-1(3(5),4)-yl)quinoxalines published from 1978 until present.

C28H20FN3O2S, triclinic, P1̄ (no. 2), a = 9.1325(7) Å, b = 11.5184(9) Å, c = 11.6535(9) Å, α = 74.682(7)°, β = 84.253(6)°, γ = 76.720(6)°, V = 1149.68(15) Å3, Z = 2, R gt(F) = 0.0574, wR ref(F 2) = 0.1438, T = 296(2) K.

C23H16N2OS, orthorhombic, Pna21 (no. 33), a = 19.4988(9) Å, b = 19.5060(9) Å, c = 9.2893(4) Å, V = 3533.1(3) Å3, Z = 8, R gt(F) = 0.0501, wR ref(F 2) = 0.1269, T = 296(2) K.

C28H23F2N3OS, monoclinic, I2/a (no. 15), a = 20.3481(8) Å, b = 10.2647(4) Å, c = 23.6975(11) Å, β = 105.317(5)°, V = 4773.8(4) Å3, Z = 8, R gt(F) = 0.0489, wR ref(F 2) = 0.1543, T = 296(2) K.

C23H16ClN5O, monoclinic, P21/c (no. 14), a = 10.0503(6) Å, b = 17.5265(9) Å, c = 22.8763(16) Å, β = 91.554(6)°, V = 4028.1(4) Å3, Z = 8, R gt(F) = 0.0748, wR ref(F 2) = 0.2274, T = 296(2) K.

According to the biological screening reports, a thiadiazoloquinazoline scaffold constitutes a promising source of inspiration for the synthesis of novel bioactive molecules. The current review art...

3-(Benzofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde was used, as a precursor for the synthesis of a series of novel heterocycles by facile reactions with 3-oxo-3-phenylpropanenitrile, 2-cyanoethanethioamide, and various hydrazides such as cyanoacetohydrazide, acetohydrazide, and carbohydrazide derivatives. The structures of the products were confirmed by various spectroscopic methods along with the X-ray crystal structures.

This review deals with the methods for the synthesis of various bicyclic pyrimidothiazines which are not annelated with other cycles. Syntheses of pyrimido[2,1-b]-, pyrimido[4,5-b]-, pyrimido[5,4-e...

Series of novel 1,2-bis((3-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazines 4 and 2-(5-(3-(1,2,3-triazol-4-yl)pyrazol-4-yl) pyrazol-1-yl)thiazoles 13 were synthesized using simple and convenient procedures, and their structures were established. Treatment of pyrazole-4-carbaldehydes 1 with methyl ketones in alkaline medium gave the corresponding (E)-1-aryl-3-(3-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-ones 3 in 82–86% yields. Treatment of 3 with hydrazine hydrate gave 4, in 69–75% yields, rather than the expected 1-aryl-5-methyl-4-(1-aryl-4-(3-phenyl-4,5-dihydro-1H-pyrazol-5-yl)-1H-pyrazol-3-yl)-1H-1,2,3-triazoles. Reactions of 3 with thiosemicarbazide gave the corresponding carbothioamides 9 which in reaction with phenacyl bromides gave the corresponding dihydropyrazolylthiazoles 13 in 82–87% yields. The novel synthesized product exhibits good antimicrobial activities against the tested microorganisms.

C18H17N5O2, monoclinic, P21/n (no. 14), a = 20.3702(7) Å, b = 7.3482(2) Å, c = 23.2504(10) Å, β = 106.507(4)°, V = 3336.8(2) Å3, Z = 8, R gt(F) = 0.0571, wR ref(F 2) = 0.1507, T = 296(2) K.

C27H23F2N3S, 0.5(C3H7NO), monoclinic, C2/c (no. 15), a = 25.1579(10) Å, b = 9.9356(4) Å, c = 20.1799(7) Å, β = 91.741(4)°, V = 5041.8(3) Å3, Z = 8, R gt(F) = 0.0508, wR ref(F 2) = 0.1385, T = 296(2) K.

C22H22N8O2, monoclinic, P21/c (no. 14), a = 15.5175(5) Å, b = 7.9715(3) Å, c = 17.3941(5) Å, β = 90.005(3)°, V = 2151.61(12) Å3, Z = 4, R gt(F) = 0.0592, wR ref(F 2) = 0.1780, T = 293(2) K.

The molecule of the title compound, C26H17ClFN3OS, comprises benzofuranyl (A), thiazolyl (B), pyrazolyl (C), chlorophenyl (D) and fluorophenyl (E) ring systems. Rings A–D are almost coplanar, as indicated by the twist angles between the ring pairs A/B, B/C and C/D of 7.6 (1), 4.7 (1) and 6.9 (2)°, respectively. Ring E is twisted by 73.2 (1)° from the plane through ring C. In the crystal, pairwise C—H...F interactions link the molecules into inversion dimers. Aromatic π–π interactions are also observed between rings A and E and between rings B and C for neighbouring pairs of molecules related by inversion symmetry. Taken together, the weak interactions generate [010] chains.

The title molecule, C22H21FN8O, comprises fluorophenyl (A), methyltriazolyl (B), methyltriazolyl (C) and tolyl (D) rings. The twist angles between the planes through neighbouring ring pairs A/B, B/C and C/D are 45.0 (1), 9.4 (1) and 43.2 (1)°, respectively. Intermolecular π–π interactions between rings A and C and between B and D propagate the structure in the [010] direction and weak C—H...O interactions also occur.

The title molecule, C25H17ClFN3S, contains indenothiazolyl (A), pyrazolyl (B), fluorophenyl (C) and chlorophenyl (D) groups. The dihedral angles between the ring planes A/B, B/C and B/D are 14.2 (1), 83.0 (1) and 6.5 (2)°, respectively. In the crystal, pairs of molecules related by inversion symmetry are linked by pairwise weak C—H...N interactions, forming dimers. These dimers interact through π–π contacts between the thiazolyl units [centroid-to-centroid distance = 3.826 (1) Å], forming chains along [010].

The main molecule of the title dimethylformamide monosolvate, C28H20BrN7O2S·C3H7NO, comprises bromophenyl (A), thiadiazolyl (B), pyrazolyl (C), phenyl (D) and indolyl (E) ring systems with twist angles between the planes through neigbouring rings A/B, B/C, C/D and C/E of 33.7 (1), 14.8 (1), 60.7 (2) and 20.9 (1)°, respectively. In the crystal, the molecules are related by c-glide symmetry to form columns parallel to [001] which are linked by intermolecular N—H...O, C—H...O and C—H...Br contacts.

The asymmetric unit of the title compound, C20H17N5O, consists of two independent molecules. The molecules comprise tolyl (A), triazolyl (B), pyrazolecarbaldehydyl (C) and phenyl (D) groups. The angles between the planes through neighouring rings A/B, B/C and C/D are 39.1 (1), 6.0 (1) and 12.6 (1)°, respectively, for the first molecule and 46.0 (1), 4.6 (1) and 8.5 (2)°, respectively, for the second. In the crystal, the two independent molecules form dimers linked by four C—H...O hydrogen bonds with each O atom accepting two such links.