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Design, Synthesis and Evaluations of New 10‐Triazolyl‐1‐methoxygenipin Analogues for Their Cytotoxicity to Cancer Cells
Author(s) -
Silalai Patamawadee,
Sirion Uthaiwan,
Piyachaturawat Pawinee,
Chairoungdua Arthit,
Suksen Kanoknetr,
Saeeng Rungnapha
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202001908
Subject(s) - genipin , cytotoxicity , gardenia jasminoides , chemistry , stereochemistry , cancer cell lines , silylation , silyl ether , cytotoxic t cell , combinatorial chemistry , cancer cell , biochemistry , cancer , biology , in vitro , chitosan , medicine , alternative medicine , pathology , genetics , catalysis
Genipin 1 , derived from geniposide present in the fruit of Gardenia jasminoides Ellis has been reported to show diverse pharmacological activity. In this work, a new series of genipin‐triazole analogues was designed and synthesized yielding high yields from naturally genipin and their cytotoxicity evaluated against six cancer cell lines. Twenty‐seven analogues were obtained using a convenient four‐step reaction methods. Six analogues showed higher cytotoxic activity than the original genipin and benzylether‐triazolegenipin 5 j exhibited the strongest activity against P‐388 and A‐549 cancer cell lines with IC 50 values of 2.54 and 4.53 μM. The structure‐activity relationships (SARs) study indicated that the introduction of dibenzyl ether, substituted silyl and long chain aliphatic‐triazoles at C‐10 position of genipin were most effective in improving cytotoxicity. Molecular docking results provided the information for further modification of genipin scaffold for development as cytotoxic agent.