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An efficient, ultrasound assisted catalyst-free, green protocol has been developed for the synthesis of 1,2,3-triazolyl phenylhydrazone derivatives under environmentally benign condition. The antioxidant activity for all the synthesized derivatives were evaluated in vitro by using 1,1-diphenylpicrylhydrazyl (DPPH) radical scavenging method. The compounds 6a, 6e, 6f, and 6i were shows an excellent antioxidant activity than the standard drug butylated hydroxy toluene with IC50 values in the range 12.03 ± 0.11–14.07 ± 0.31 µg/mL. Molecular docking study was also performed to elaborate their possible interactions with Myeloperoxidase enzyme. Furthermore, in silico ADME properties for all the compounds were also studied. [ABSTRACT FROM AUTHOR]

The article provides a comprehensive overview of various synthetic approaches to 1,2,3-triazoles, focusing on up-to-date procedures from 2000 to 2023. The significance of 1,2,3-triazoles in pharmaceuticals and their diverse applications in different fields is highlighted. The text covers classical methods as well as modern approaches, including Cu-catalyzed cycloaddition reactions and metal-free methods, under microwave, ultrasound, and continuous flow conditions. The review emphasizes the importance of click chemistry in simplifying and enhancing the synthesis of 1,2,3-triazoles for future molecular diversity explorations. [Extracted from the article]

We have described one-pot multicomponent synthesis of 2-amino-3,5-dicyano-6-phenylthiopyridine incorporated1,2,3-triazole derivatives from triazolyl aldehydes, malononitrile and thiophenol in excellent yields. The antitubercular, antifungal and antioxidant activity for all the synthesized derivatives were evaluated. The antifungal activity results show that the compounds 12a, 12b and 12g were observed more potent than Miconazole with MIC value <25 µg/mL. Whereas, the antitubercular screening against MTB H37Rv strain did not produce any promising results. Furthermore, in silico ADME properties for all the compounds were also studied and exhibited the potential to be developed as an oral drug candidate. [ABSTRACT FROM AUTHOR]

In search of new biologically potent molecules a small focused library of new guanidine-1,2,3-triazole hybrid derivatives were synthesized via Organocatalytic enolate- mediated azide-carbonyl [3 + 2] cycloaddition yielding a highly functionalized triazole core structure. The synthesis of all the derivatives were confirmed by spectral analysis 1H NMR, 13C NMR and MS. The new guanidine-1,2,3-triazole conjugates were found to exhibit promising anti-inflammatory and antioxidant activity. The anti-inflammatory activity screened by membrane stabilization method summarizes the four potential conjugates 5c, 5f, 5h and 5g to be potent in comparison with standard drug Diclofenac sodium (DFS). The conjugates were also assessed for antioxidant potential by DPPH method. Among all the synthesized compounds, the compounds 5d, 5f, 5g and 5h exhibited potent antioxidant activity. Molecular docking study was performed to gain insight into the putative binding mode and binding strength of these compounds with the target enzyme Cyclo-oxygenase (COX-2) enzyme. The in vitro and in silico studies together with simpler designing and synthesis strategy via Organocatalytic enolate- mediated azide-carbonyl [3 + 2] cycloaddition followed by a two-component reaction with guanidine in basic conditions rationalize guanidine-1,2,3-triazole hybrid derivatives as easily assessable novel therapeutic agents. [ABSTRACT FROM AUTHOR]

In search of new active molecules, a small focused library of 1,2,3-triazoles based 2,4-thiazolidinedione derivatives has been efficiently prepared via the click chemistry approach. Several derivatives were exhibited excellent anti-inflammatory activity compared to the standard drug. Further, the synthesized compounds were found to have potential antioxidant activity. Furthermore, to rationalize the observed biological activity data, the molecular docking study has also been carried out against the active site of inflammation enzyme PPARγ, which revealed a significant correlation between the binding score and biological activity for these compounds. The results of the in vitro and in silico study suggest that the triazole incorporated 2,4-thiazolidinedione derivatives may possess the ideal structural requirements for the further development of novel therapeutic agents. [ABSTRACT FROM AUTHOR]

A series of new benzimidazole incorporated 3,5-bis (arylidene)-4-piperidones were synthesized by using aryl aldehydes, piperidinone, 2-(chloromethyl)-benzimidazole and DBU acetate [DBUH][OAc] act as a catalyst under solvent free condition in excellent yields. The synthesized compounds were screened for their in vitro antimycobacterial activity against M. tuberculosis H37Ra (MTB) and M. bovis BCG strains. The compounds 4a, 4b, 4e, 4i, 4k and 4l are highly potent against both the strains. Most of the active compounds are non-cytotoxic against MCF-7, A549, HCT 116 and THP-1 cell lines. Furthermore, a molecular docking study of these compounds was carried out to investigate their binding pattern with the target, active site of mycobacterial enoyl-acyl carrier protein reductase (Inh A). Therefore, these compounds can be subjected for further optimization and drug development which could give promising chemical leads for treatment of TB. [ABSTRACT FROM AUTHOR]

We have developed a convenient one-pot multicomponent synthesis of highly functionalized [1,6]-naphthyridines under solvent free condition using [Et3NH][HSO4] in excellent yield. This protocol offers several advantages, including short reaction time, simple experimental workup procedure and no toxic byproducts, avoids the use of toxic organic solvents and anhydrous conditions. Further. we have screened the synthesized naphthyridines for in vitro antibacterial, antifungal and antioxidant activity. Furthermore, a molecular docking study of these compounds was carried out to investigate their binding pattern with the target, β-Ketoacyl-acyl carrier protein synthase III (FabH). Finally, the ADME parameters for these compounds showed good drug like properties and can be developed as oral drug candidates. [ABSTRACT FROM AUTHOR]

An approach toward the synthesis of novel conjugates of 3,5-bis (arylidene)-4-piperidones (DAP) pharmacophore with amide-linkage has been developed via one-pot multicomponent reaction of aryl aldehydes, piperidinone and 2-chloro-N-phenylacetamide using [Et3NH][HSO4] as a catalyst/medium. Both substitutions on arylidene rings and piperidinone nitrogen (substituted 2-chloro-N-phenylacetamide) were varied. The synthesized conjugates were evaluated for their in vitro antitubercular activity against M. tuberculosis H37Ra (MTB) and M. bovis BCG strains. Among the series, compounds 4f, 4g, 4i and 4j showed remarkable broad spectrum antitubercular activity with low IC50 values. Furthermore, computer docking simulations, for the most active conjugates were performed with the active site of mycobacterial enoyl-acyl carrier protein reductase (InhA) support the antitubercular activity. Lower cytotoxicity, high potency and promising activity against MTB and M. Bovis BCG suggest that amide linked DAP could serve as good leads for further modifications and development. [ABSTRACT FROM AUTHOR]

A series of new 1,2,3‐triazolidene‐indolinone derivatives (17a‐j) were designed and synthesized via [Et3NH] [HSO4] catalyzed solvent‐free approach. The synthesis strongly relied on Knoevenagel condensation of 1,4‐disubstituted 1,2,3‐triazolyl aldehydes (15a‐j) and oxindole (5). The solvent‐free approach and Brønsted acidity of [Et3NH] [HSO4] ionic liquid increased the rate of reaction and provided the corresponding 1,2,3‐triazolidene‐indolinone derivatives (17a‐j) in excellent yields. The reusability of ionic liquid is also established with persistent effective yields up to four cycles. These novel 1,2,3‐triazolidene‐indolinone derivatives may exhibit potential biological response due to the presence of potent moieties and presence of triazolidene‐exocyclic double bond. [ABSTRACT FROM AUTHOR]

In search of new active molecules, a small focused library of tetrazoloquinoline-based 1,2,3-triazoles has been efficiently prepared via click chemistry approach. Several derivatives were found to be exhibiting promising antimicrobial and antioxidant activity characterized by their lower minimum inhibitory concentration values. All the synthesized compounds exhibited excellent antibacterial activity against Gram negative bacteria E. coli and F. devorans and antifungal activity against C. albicans and A. niger. Further, these compounds were tested for their antitubercular activity against dormant MTB H37Ra and dormant M. bovis BCG using XRMA assay protocol and showed no significant activity. Also, the synthesized compounds were found to have potential antioxidant activity with IC50 range = 12.48–50.20 μg/mL. Furthermore, to rationalize the observed biological activity data, the molecular docking study also been carried out against the active site of fungal C. albicans enzyme P450 cytochrome lanosterol 14α-demethylase, which revealed a significant correlation between the binding score and biological activity for these compounds. The results of the in vitro and in silico study suggest that the triazole-incorporated tetrazoloquinolines may possess the ideal structural requirements for further development of novel therapeutic agents. [ABSTRACT FROM AUTHOR]