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Design and Synthesis of Novel Nonsteroidal Phytoestrogen‐based Probes as Potential Biomarker: Evaluation of Anticancer Activity and Docking Studies
Author(s) -
Kumar Sumit,
Verma Nishant,
Zubair Swaleha,
Faisal Syed Mohd,
Kazmi Shadab,
Chakraborty Sudipta,
Owais M.,
Ahmed Naseem
Publication year - 2017
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2812
Subject(s) - chemistry , flavones , hela , docking (animal) , in vitro , stereochemistry , estrogen receptor , biological activity , molecular model , biochemistry , combinatorial chemistry , pharmacology , cancer , breast cancer , chromatography , medicine , nursing
Two series of novel flavones and flavone‐tanaproget conjugates were designed, synthesized, 125 Iradiolabeled, and evaluated for their antiproliferative activity against human cancer cell lines (MCF‐7, MDA‐MB‐231, and HeLa). They exhibited good‐to‐excellent in vitro antiproliferative activity. For improving the receptor‐binding affinity of synthesized compounds, flavone‐tanaproget moieties were linked together through alkyl‐alkenyl chain spacer, and the butyl chain was substituted at C‐3 position of oxa‐ and aza‐flavones to enhance the lypophilicity of the molecule. These compounds are hypothesized to bind with estrogen and progesterone receptors by docking studies, and binding affinities were shown to increase significantly compared with the reference ligands.