Synthesis and biological evaluation of a series of 1,4-disubstituted 1,2,3-triazole derivatives as possible antimicrobial agents

Jadhav, Rahul P.; Raundal, Hemant N.; Patil, Amar; Bobade, Vivek D.

doi:10.1016/j.jscs.2015.03.003

Cited by 39 publications

(17 citation statements)

References 32 publications

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“…According to the reports by Jain et al 94 , 1-(4-chlorophenyl)-1-propyl piperazine and 1-(4-methylphenyl)-1-propyl piperazine exhibited excellent inhibitory activity against S. aureus and P. aeruginosa respectively. Jadhav et al 95 reported strong antibacterial and antifungal activity by different piperazine group of compounds. Thus, it can be concluded that propanoic acid decyl ester, propanoic acid,3-mercapto-dodecyl ester, 3-(phenylmethyl)-2,5-piperazinedione and N-acetyl-3-methyl-1,4-diazabicyclo[4.3.0]nonan-2,5-dione present in EA-Kz-24 might have a significant role to play in its inhibitory effect against a wide range of test microorganisms which is reported for the first time.…”

Section: Discussionmentioning

confidence: 99%

Antimicrobial biosynthetic potential and diversity of culturable soil actinobacteria from forest ecosystems of Northeast India

Sharma

Thakur²

2020

Sci Rep

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Actinobacteria is a goldmine for the discovery of abundant secondary metabolites with diverse biological activities. this study explores antimicrobial biosynthetic potential and diversity of actinobacteria from Pobitora Wildlife Sanctuary and Kaziranga National Park of Assam, India, lying in the Indo-Burma mega-biodiversity hotspot. A total of 107 actinobacteria were isolated, of which 77 exhibited significant antagonistic activity. 24 isolates tested positive for at least one of the polyketide synthase type I, polyketide synthase type II or non-ribosomal peptide synthase genes within their genome. their secondary metabolite pathway products were predicted to be involved in the production of ansamycin, benzoisochromanequinone, streptogramin using DoBISCUIT database. Molecular identification indicated that these actinobacteria predominantly belonged to genus Streptomyces, followed by Nocardia and Kribbella. 4 strains, viz. Streptomyces sp. PB-79 (GenBank accession no. KU901725; 1313 bp), Streptomyces sp. Kz-28 (GenBank accession no. KY000534; 1378 bp), Streptomyces sp. Kz-32 (GenBank accession no. KY000536; 1377 bp) and Streptomyces sp. Kz-67 (GenBank accession no. KY000540; 1383 bp) showed ~89.5% similarity to the nearest type strain in EzTaxon database and may be considered novel. Streptomyces sp. Kz-24 (GenBank accession no. KY000533; 1367 bp) showed only 96.2% sequence similarity to S. malaysiensis and exhibited minimum inhibitory concentration of 0.024 µg/mL against methicilin resistant Staphylococcus aureus ATCC 43300 and Candida albicans MTCC 227. This study establishes that actinobacteria isolated from the poorly explored Indo-Burma megabiodiversity hotspot may be an extremely rich reservoir for production of biologically active compounds for human welfare. Since ancient times, mankind has been exploring nature for bioactive organisms to treat different ailments. More than 100000 natural products have been identified in the last 150 years, which include highly assorted chemical classes such as polyketides, alkaloids, non-ribosomal peptides, isoprenoids or phenylpropanoids 1,2. Microbial biodiversity can provide us with the richest and the most versatile reservoir of potentially active natural products. A large portion of genomes from beneficial microbes are dedicated to the production of these valuable natural products. A single microbe is capable of making 30-50 natural product compounds 3. There are approximately 1 million natural products out of which about 25% are biologically active showing either positive activity or toxicity. Among the prospective sources of natural products, bacteria are prolific sources and a vast majority of these products are produced by a phylum of Gram-positive bacteria known as the "Actinobacteria" 4-6. Actinobacteria are diverse group of bacteria with high content of guanosine-cytosine (65-75%) ranging from 2.5-9.7 Mb genome size 7. Among actinobacteria, about 75% of antibiotics such as ivermectin, streptomycin, nystatin and tetracycline are produced by the microbial world's...

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Section: Discussionmentioning

confidence: 99%

Antimicrobial biosynthetic potential and diversity of culturable soil actinobacteria from forest ecosystems of Northeast India

Sharma

Thakur²

2020

Sci Rep

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“…Nonetheless, 1,3,4‐thiadiazole, 1,3,4‐oxadiazole, and 1,2,4‐triazole substituents are known as the most active isomers. However, chemotherapy still remains the most significant application field for heterocyclic compounds …”

Section: Introductionmentioning

confidence: 99%

In vitro cytotoxic and in vivo antitumoral activities of some aminomethyl derivatives of 2,4‐dihydro‐3H‐1,2,4‐triazole‐3‐thiones—Evaluation of their acetylcholinesterase and carbonic anhydrase enzymes inhibition profiles

Timur

Koçyiğit

Daştan

et al. 2018

J Biochem & Molecular Tox

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The 1,2,4‐triazole and its derivatives were reported to exhibit various pharmacological activities such as antimicrobial, analgesic, anti‐inflammatory, antitumoural, cytotoxic, and antioxidant properties. In this study, a series of triazole compounds (M1‐M10) were evaluated for some biological activities. In vitro qualifications of these compounds on acetylcholinesterase (AChE) and human carbonic anhydrase enzyme activities were performed. Also, their antitumoral activities in human colon cancer (HT29) cell line cultures were examined. In addition, colon cancer experimentation was induced in rats by an in vivo method, and the in vivo anticancer effects of triazole derivatives were investigated. Also, the effects of these derivatives in levels of antioxidant vitamin A, vitamin E, and MDA were studied in rat liver and blood samples. Most of the compounds were found to exhibit significant antioxidant and antitumoral activities. All the compounds had cytotoxic activities on HT29 cell lines with their IC50 values lower than 10 µM concentrations. The low IC 50 values of the compounds are M1 (3.88 µM), M2 (2.18 µM), M3 (4.2 µM), M4 (2.58 µM), M5 (2.88 µM), M6 (2.37 µM), M7 (3.49 µM), M8 (4.01 µM), M9 (8.90 µM), and M10 (3.12 µM).

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“…They are known to possess a wide range of pharmacological activities like anti-microbial, 9,10 anti-inammatory, 11 anti-tubercular, 12 anti-diabetic, 13 anti-malarial, 14 antioxidant, 15 and anti-cancer activities. The basic heterocyclic rings present in various medicinal agents are mainly 1,2,3-triazoles and pyrazoles.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and characterization of new 1,2,3-triazolyl pyrazole derivatives as potential antimicrobial agents via a Vilsmeier–Haack reaction approach

et al. 2016

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The synthesis of a new series of 3-{5-methyl-1-[2-methyl-3-(trifluoromethyl) phenyl/substituted phenyl]-1H-1,2,3-triazol-4-yl}-1-(aryl)-1H-pyrazole-4-carbaldehyde compounds (5a-n) was carried out via a Vilsmeier-Haack formylation of 4-{(1E)-1-[2-(aryl) hydrazinylidene]ethyl}-5-methyl-1-[2-methyl-3-(trifluoromethyl)phenyl/substituted phenyl]-1H-1,2,3-triazole (4a-n) with a phosphorous oxychloride and DMF mixture. The newly synthesized compounds were characterized using IR, 1 H NMR, 13 C NMR, mass spectral data and elemental analysis. The newly synthesized compounds were screened for their in vitro anti-bacterial, anti-fungal and anti-oxidant activities. Some of the synthesized compounds displayed a broad spectrum of antimicrobial activities and moderate to good anti-oxidant activities. The antibacterial results were further supported by in silico molecular docking studies of these compounds for the inhibition of E. coli MurB enzyme (PDB code: 2MBR) and showed a minimum binding energy and good affinity towards the active pocket comparable with the standard drug Ciproflaxin. Thus, they may be considered as good inhibitors of the E. coli MurB enzyme (PDB code: 2MBR).Scheme 1 Synthetic scheme for compounds 5a-n. This journal is

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Synthesis and biological evaluation of a series of 1,4-disubstituted 1,2,3-triazole derivatives as possible antimicrobial agents

Cited by 39 publications

References 32 publications

Antimicrobial biosynthetic potential and diversity of culturable soil actinobacteria from forest ecosystems of Northeast India

Antimicrobial biosynthetic potential and diversity of culturable soil actinobacteria from forest ecosystems of Northeast India

In vitro cytotoxic and in vivo antitumoral activities of some aminomethyl derivatives of 2,4‐dihydro‐3H‐1,2,4‐triazole‐3‐thiones—Evaluation of their acetylcholinesterase and carbonic anhydrase enzymes inhibition profiles

Design, synthesis and characterization of new 1,2,3-triazolyl pyrazole derivatives as potential antimicrobial agents via a Vilsmeier–Haack reaction approach

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