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Synthesis of 2,5‐Disubstituted‐1,3,4‐oxadiazole Derivatives and Their Evaluation as Anticancer and Antimycobacterial Agents
Author(s) -
Polkam Naveen,
Kummari Bhaskar,
Rayam Parsharamulu,
Brahma Umarani,
Ganga Modi Naidu Vegi,
Balasubramanian Sridhar,
Anireddy Jaya Shree
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201701101
Subject(s) - oxadiazole , antimycobacterial , chemistry , bromide , stereochemistry , bioisostere , du145 , in vitro , moiety , combinatorial chemistry , medicinal chemistry , chemical synthesis , organic chemistry , biochemistry , mycobacterium tuberculosis , biology , medicine , tuberculosis , pathology , cancer , cancer cell , lncap , genetics
Abstract A series of regioisomeric (2,5‐dimethoxybenzoic acid, veratric acid) analogues were prepared by swapping the carboxylic motif to its oxadiazole bioisostere and have been screened for in vitro anticancer studies by using MTT (3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide) colorimetric assay. All of them were well characterized by spectroscopic techniques. Among the screened compounds, 9 i (2‐(2,5‐dimethoxyphenyl)‐5‐(5‐phenylthiophen‐2‐yl)‐1,3,4‐oxadiazole) demonstrated superior activity against MDA231 cells. Products 9 i displayed excellent activity against DU145, HCT15 and 10 i (2‐(3,4‐dimethoxyphenyl)‐5‐(5‐phenylthiophen‐2‐yl)‐1,3,4‐oxadiazole) against MDA231 cells. Structure of 10 c (2‐(3,4‐dimethoxyphenyl)‐5‐(2,4,6‐trimethoxyphenyl)‐1,3,4‐oxadiazole) was further authenticated through single crystal X‐ray diffraction. Analogue 9 i have come out to be the best anticancer and antimycobacterial agent.