Synthesis, antifungal evaluation and in silico study of novel Schiff bases derived from 4-amino-5(3,5-dimethoxy-phenyl)-4H-1,2,4-triazol-3-thiol

Moorthy, N. S. Hari Narayana; Vittal, Udugade B.; Karthikeyan, Chandrabose; Thangapandian, V.; Venkadachallam, A.P.; Trivedi, Piyush

doi:10.1016/j.arabjc.2013.12.021

Cited by 15 publications

(6 citation statements)

References 25 publications

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“…1). On the other hand, the remarkable biological effects of aldiminetype Schiff base especially those bearing 1,2,4-triazole template such as antitumor, tyrosine kinase inhibitory effect, anticonvulsant, antidepressant, lipid-lowering, and antihypertensive as well as antimalarial, antifungal, and antiviral activities introduced Schiff base as considerable functional groups [27,28]. In addition, some Schiff bases are known to play an important role in physiological chemistry such as vision processing and enzymatic activity [29].…”

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confidence: 99%

Novel Aldimine‐Type Schiff Bases of 4‐Amino‐5‐[(3,4,5‐trimethoxyphenyl)methyl]‐1,2,4‐triazole‐3‐thione/thiol: Docking Study, Synthesis, Biological Evaluation, and Anti‐Tubulin Activity

Ameri

Khodarahmi

Hassanzadeh

et al. 2016

Archiv der Pharmazie

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The present study was planned to design some novel aldimine-type Schiff bases bearing 3,4,5-trimethoxyphenyl and 1,2,4-triazole-3-thione/thiol as potential tubulin polymerization inhibitors. The obtained results of the molecular docking study using the tubulin complex (PDB code: 1SA0) showed that compounds H-25 and H-26 were well fitted in the colchicine binding site of tubulin with binding energies of -8.68 and -8.40 kcal/mol, respectively, in comparison to the main ligand (-8.20 kcal/mol). In parallel, molecular simulations were also performed on five other 3,4,5-trimethoxyphenyl-containing ligand targets including hsp90, VEGFR2, and human and microbial (Staphylococcus aureus and Candida albicans) dihydrofolate reductase, among which H-17, H-45, H-27, H-02, and H-19 were the most suitable compounds, respectively. Evaluation of the cytotoxic effect of the most efficient compounds of the docking steps (H-25) revealed IC50 values of 12.48 ± 1.10, 4.25 ± 0.22, 3.33 ± 0.31, and 9.71 ± 0.75 µM against the HT1080, HT29, MCF-7, and A549 cell lines, respectively, compared to doxorubicin (12.69 ± 1.23, 6.12 ± 0.47, 3.51 ± 0.32, and 6.40 ± 0.31 µM, respectively). The in vitro tubulin polymerization investigation launched compounds H-25 and H-26 as potent antitubulin agents due to their IC50 values of 0.17 ± 0.01 and 10.93 ± 0.43 µM, respectively.

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confidence: 99%

Novel Aldimine‐Type Schiff Bases of 4‐Amino‐5‐[(3,4,5‐trimethoxyphenyl)methyl]‐1,2,4‐triazole‐3‐thione/thiol: Docking Study, Synthesis, Biological Evaluation, and Anti‐Tubulin Activity

Ameri

Khodarahmi

Hassanzadeh

et al. 2016

Archiv der Pharmazie

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“…The synthesis of 4-amino-5-phenyl-4H-1,2,4-triazole-3-thiol(3a-3c) was carried out from benzoic acid derivatives (1) and thiocarbohydrazide (2) as per the literature. [ 14 ] Intermediate compound (3) was treated with substituted aromatic aldehydes (4) in the presence of concentrated H 2 SO 4 , and yielded Schiff bases (5) The structures of the synthesized compounds were confirmed by NMR, IR, Mass and elemental analysis [Schemes 1 and 2 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, antifungal and antibacterial activity of novel 1,2,4-triazole derivatives

Gupta¹,

Jain²

2015

J Adv Pharm Technol Res

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A large number of 1,2,4-triazole-containing ring system have been incorporated into a wide variety of therapeutically interesting drug candidates including anti-inflammatory, central nervous system stimulants, antianxiety, and antimicrobial agents. To overcome the rapid development of drug resistance, new agents should preferably have chemical characteristics that clearly differ from those of existing agents. Thus led to the design and synthesize the new antimicrobial agents. A novel series of Schiff bases based on of 4-(benzylideneamino)-5-phenyl-4H-1,2,4-triazole-3-thiol scaffold was prepared by heating thiocarbohydrazide and substituted benzoic acid and subsequently, treating with substituted benzaldehydes. Seventeen derivatives were synthesized and were biologically screened for antifungal and antibacterial activity. The newly synthesized derivatives of triazole showed antifungal activity against fungal species, Microsporum gypseum; and antibacterial activity against bacterial species, Staphylococcus aureus. It was observed that none of the compounds tested showed positive results for fungi Candida albicans fungi Aspergillus niger, nor against bacterial strain Escherichia coli. Strong antifungal effects were obtained for the synthesized compounds against M. gypseum and were superior or comparable to standard drug ketoconazole. Similarly, all of the synthesized compounds exhibit strong antibacterial activity against S. aureus and were superior or comparable to standard drug streptomycin. It was found that among the triazole derivatives so synthesized, six of them, showed antifungal activity superior to ketoconazole while one of them, showed antibacterial activity superior to streptomycin. Thus, these can be the potential new molecule as an antimicrobial agent.

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“…The product was collected by filtration and washed with ethanol several times until the acidity of the filtrate disappeared and it was dried in a temperature oven 60 C o . (10)…”

Section: Synthesis Thiocode DI Carbohydrazide Tdchmentioning

confidence: 99%

Preparing Some Nano Composites Decorated with Some Pharmaceutical Compounds and Evaluating their Biological Effectiveness

Shakir

2023

IJMRA

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The aim of this study was to use electrochemical methods to synthesise and characterise several derivatives of graphene oxide or nanosheets of reduced graphene oxides (A3) and (A4). Melting-point analysis was performed on the produced compounds. SEM, XRD, TEM, and AFM. It's not environmentally friendly, but it's quick and doesn't cost a lot of money. All of the separated chemicals can be stored safely at room temperature. Bacteria have performed biological research on compounds created using the nanotechnology approach. And assess the produced compounds' capacity to limit bacterial growth and their biological efficacy against Gram-positive and Gram-negative bacteria.

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Synthesis, antifungal evaluation and in silico study of novel Schiff bases derived from 4-amino-5(3,5-dimethoxy-phenyl)-4H-1,2,4-triazol-3-thiol

Cited by 15 publications

References 25 publications

Novel Aldimine‐Type Schiff Bases of 4‐Amino‐5‐[(3,4,5‐trimethoxyphenyl)methyl]‐1,2,4‐triazole‐3‐thione/thiol: Docking Study, Synthesis, Biological Evaluation, and Anti‐Tubulin Activity

Novel Aldimine‐Type Schiff Bases of 4‐Amino‐5‐[(3,4,5‐trimethoxyphenyl)methyl]‐1,2,4‐triazole‐3‐thione/thiol: Docking Study, Synthesis, Biological Evaluation, and Anti‐Tubulin Activity

Synthesis, antifungal and antibacterial activity of novel 1,2,4-triazole derivatives

Preparing Some Nano Composites Decorated with Some Pharmaceutical Compounds and Evaluating their Biological Effectiveness

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