Design, synthesis, antibacterial and quorum quenching studies of 1,2,5-trisubstituted 1,2,4-triazoles
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ORIGINAL PAPER
Design, synthesis, antibacterial and quorum quenching studies of 1,2,5‑trisubstituted 1,2,4‑triazoles Reshma Sathyanarayana1 · Sukesh Kumar Bajire2 · Boja Poojary1 · Rajesh P. Shastry2 · Vasantha Kumar3 · Revanasiddappa Bistuvalli Chandrashekarappa4 Received: 12 April 2020 / Accepted: 9 October 2020 © Iranian Chemical Society 2020
Abstract In view of discovering novel bioactive molecules, 1-phenyl-1H-2-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-3-(N-arylcarbamoylmethylthio)-1,2,4-triazoles (8a–n) were designed and synthesized in good yield. Preliminary antibacterial activity was tested against Chromobacterium violaceum and Xanthomonas campestris pv. Campestris (Xcc). Out of 14 derivatives, compound 8g selectively possessed antibacterial activity against C. violaceum. Further derivatives that possessed an electronwithdrawing group and halogen atoms in N-phenylacetamide moiety were moderately active against Xcc (plant pathogen). After observing the reduction of violacein production through plate assay, compounds 8a, 8c, 8h, 8i and 8m were subjected to quantification of quorum sensing inhibition. Compounds with the electron-withdrawing group in N-phenylacetamide moiety showed admirable activity with > 80% inhibition of violacein. Mainly compound 8c which was inactive against the growth of bacteria were identified as excellent QSI which could be a lead compound for further development. Graphic abstract One of the best approaches to acquire anti-virulence strategies and new direction for the discovery of antibacterial drugs
Keywords 1,2,3-Triazole · 1,2,4-Triazole · Quorum quenching · Molecular docking · ADME · Xcc
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s13738-020-02093-9) contains supplementary material, which is available to authorized users. * Boja Poojary [email protected] Extended author information available on the last page of the article
Introduction Antibiotic resistance is a common problem worldwide due to the selection pressure from human applications of antibiotics. The pathogenic bacteria use various mechanisms to get shelter against antimicrobials. Due to this, bacteria
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attain genotypic and phenotypic resistance to antibiotics and emerge as superbugs [1]. As a result, antibiotic treatments remain ineffective to the patients [2]. Hence, it’s the foremost duty of the researchers to discover novel targets with better mechanisms of action [3, 4]. Among several mechanisms, quorum sensing (QS) inhibition shows to be an encouraging approach, as these molecules will not prompt resistance [5]. These pathogenic bacteria communicate by producing low molecular weight chemical signalling molecules called autoinducers (AIs) by the process called quorum sensing [6]. Bacteria use QS signalling pathway to govern virulence factor and biofilm formation which help in antibiotic resistance. Hence, researchers believe that directing the QS as an important pathway to acquire anti-virulence with minimal risk of resistanc
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