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Structure‐Activity Relationship of Indolylkojylmethane Based on Antiproliferative Activity against Breast Cancer
Author(s) -
Koli Papita,
Mehra Rukmankesh,
Sharma Deepak K.
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.202003032
Subject(s) - kojic acid , chemistry , indole test , stereochemistry , octanal , cell culture , cancer cell lines , structure–activity relationship , apoptosis , nucleophile , cell growth , catalysis , biochemistry , cancer cell , cancer , in vitro , organic chemistry , medicine , biology , enzyme , hexanal , tyrosinase , genetics
A series of indolylkojylmethane (IKM) derivatives ( 1 – 23 ) was synthesized using a multicomponent one‐pot reaction under solvent‐free condition using a heterogeneous catalyst. The synthesized compounds were screened against breast cancer cell lines MDA‐MB‐231, MCF7, and T47D. The structure‐activity relationship revealed that IKM synthesized from aliphatic aldehydes ( 9 – 11 ) were active against all three cell lines and showed IC 50 value of 0.15 μM–3.93 μM. IKM synthesized from aromatic aldehydes having electron‐donating group ( 1 , 5 , and 6 ) specifically inhibited the proliferation of the MDA‐MB‐231 cell line. The effect of various substituted indoles ( 12 – 17 ) was also studied and observed that compound 14 synthesized from 5‐cyanoindole, specifically inhibited T47D cell line proliferation. Replacing indole ( 1 ) with nucleophiles ( 18 – 23 ) in IKM decreased the antiproliferative activity. Compound 10 synthesized from kojic acid, indole and octanal was found to be most potent with IC 50 values of 0.21, 0.15, and 3.45 μM against MDA‐MB‐231, MCF7, and T47D, respectively.