Quinolone Tethered 1,2,3-triazole Conjugates: Design, Synthesis, and Computational Docking Studies on New Heterocycles as Potent Antimicrobial Targets

Author:

Basireddy Avanthi12ORCID,Allaka Tejeswara Rao3ORCID,Allam Avekananda Reddy3,Baddam Sudhakar Reddy4,Basireddy Sravanthi56,Kishore Pilli Veera Venkata Nanda1ORCID

Affiliation:

1. Department of Chemistry, School of Applied Sciences and Humanities, Vignan's Foundation for Science, Technology & Research (VFSTR) (Deemed to be University), Vadlamudi, Guntur, Andhra Pradesh, 522213, India

2. Department of Chemistry, Malla Reddy Institute of Technology and Science, Maisammaguda, Dulapally, Hyderabad, Telangana, 500100, India

3. Centre for Chemical Sciences and Technology, Institute of Science & Technology, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, Hyderabad, Telangana, 500085, India

4. RNA Therapeutic Institute, University of Massachusetts Chan Medical School, Worcester, Massachusetts, 01655, United States of America

5. Department of Chemistry, GITAM Institute of Science, GITAM (Deemed to be University), Gandhi Nagar, Rushikonda, Visakhapatnam, Andhra Pradesh, 530045, India

6. Department of Chemistry, Institute of Aeronautical Engineering, Dundigal, Hyderabad, Telangana, 500043, India

Abstract

Abstract: The synthesis and biological properties of molecules simultaneously comprising various heterocycles, such as fused 2-quinolones and 1,2,3-triazoles, have been evaluated as a part of our ongoing research in medicinal and organic chemistry. We were successful in developing a synthetic procedure for 1,2,3-triazole substituted quinolone derivatives. Infrared, proton, and carbon nuclear magnetic resonance, mass spectroscopy and elemental analysis were used to characterise the structures of the recently synthesised triazole derivatives. From screening results, all the compounds demonstrated increased antibacterial action against both Gram-positive and Gram-negative bacteria. Moreover, 1,2,3-triazoles linked to tert-butyl benzyl (3a), trifluoromethyl benzyl (3b), 3-chlorobenzyl (3c), 4- hydroxy-3-nitrobenzyl (6b), 4-hydroxy-4-trifluoromethylbenzyl (6d), and 4-hydroxy-2,4- difluorobenzyl (6e) compounds showed promising antibacterial and antifungal activities with MICs values of 1.07-4.33 μg/mL. The prepared ligand 4-hydroxy-2,4-difluoro benzyl-1,2,3-triazole (6e) exhibited the highest docking score of -6.34 kcal/mol and showed interacting amino acid residues ArgB:1122, MetB:1121, AspB:1083, TryB:1087, AlaB:1118, AlaB:1120, GluB:1088, GlyB:1117, SerB:1084, and AlaB:1119 within the active site of 2XCT. Final scaffolds were further evaluated for their ADMET and physicochemical properties by using ADMETlab2.0 and SwissADME web servers as good oral bioavailability drugs.

Publisher

Bentham Science Publishers Ltd.

Subject

Organic Chemistry

同舟云学术

1.学者识别学者识别

2.学术分析学术分析

3.人才评估人才评估

"同舟云学术"是以全球学者为主线,采集、加工和组织学术论文而形成的新型学术文献查询和分析系统,可以对全球学者进行文献检索和人才价值评估。用户可以通过关注某些学科领域的顶尖人物而持续追踪该领域的学科进展和研究前沿。经过近期的数据扩容,当前同舟云学术共收录了国内外主流学术期刊6万余种,收集的期刊论文及会议论文总量共计约1.5亿篇,并以每天添加12000余篇中外论文的速度递增。我们也可以为用户提供个性化、定制化的学者数据。欢迎来电咨询!咨询电话:010-8811{复制后删除}0370

www.globalauthorid.com

TOP

Copyright © 2019-2024 北京同舟云网络信息技术有限公司
京公网安备11010802033243号  京ICP备18003416号-3