Isomannide monoundecenoate‐based 1,2,3‐triazoles: Design, synthesis, and in vitro bioactive evaluation

A new series of isomannide monoundecenoate‐based 1,2,3‐triazole analogs 6a–e were designed by employing click chemistry in good yields. in vitro bioactive assay manifested that the several target compounds exhibited promising antibacterial and antifungal activities. Notably, compounds having phenyl...

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Published inJournal of heterocyclic chemistry Vol. 57; no. 12; pp. 4312 - 4321
Main Authors Tangadanchu, Vijai Kumar Reddy, Gundabathini, Sandhya Rani, Bethala L. A., Prabhavathi Devi, Yedla, Poornachandra, Chityal, Ganesh Kumar
Format Journal Article
LanguageEnglish
Published Chichester, UK John Wiley & Sons, Inc 01.12.2020
Wiley
Wiley Subscription Services, Inc
Subjects
Biological activity
Biotechnology
Cancer
Chemical synthesis
Chemistry
Chemistry, Organic
Cytotoxicity
Fungicides
Lead compounds
Physical Sciences
Science & Technology
Substitutes
Triazoles
CYCLOADDITION
SERIES
BIOLOGICAL EVALUATION
ANTIBACTERIAL
1,2-EPOXIDES
CONJUGATES SYNTHESIS
AZIDE
POTENT INHIBITORS
DERIVATIVES
TRIAZOLES
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Summary:A new series of isomannide monoundecenoate‐based 1,2,3‐triazole analogs 6a–e were designed by employing click chemistry in good yields. in vitro bioactive assay manifested that the several target compounds exhibited promising antibacterial and antifungal activities. Notably, compounds having phenyl substituted triazole 6a, and hydroxy phenyl substituted triazole 6b possessed highly selective promising inhibition towards Gram‐positive bacterial strains namely Bacillus subtilis and Staphylococcus aureus with MIC value of 3.9 μg/mL. Further, these potential hybrids (6a and 6b) also exhibited highly impressive antifungal activity against the tested panel of Candida strains with MIC value of 3.9 μg/mL. Based on our in vitro preliminary antimicrobial study, these two compounds 6a and 6b have been identified as potential antimicrobial lead compounds. Moreover, all prepared derivatives were also evaluated for their in vitro cytotoxic activities against A549, MCF7, DU145 and HeLa cancer cell lines. The results indicated that only the hydroxy phenyl substituted triazole analog 6b displayed good cytotoxic activity towards all tested human cancer cell lines without any significant effects on normal cell line (HUVEC).
Bibliography:Funding information
University Grants Commission (UGC), New Delhi, India; Council of Scientific and Industrial Research (CSIR), India
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.4138