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Synthesis, Antiproliferative, and c‐Src Kinase Inhibitory Activities of 4‐Oxo‐4 H ‐1‐benzopyran Derivatives
Author(s) -
Chand Karam,
Tiwari Rakesh K,
Kumar Sumit,
Shirazi Amir Nasrolahi,
Sharma Sweta,
Van der Eycken Erik V,
Parmar Virinder S,
Parang Keykavous,
Sharma Sunil K
Publication year - 2015
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.2106
Subject(s) - chemistry , benzopyran , kinase , proto oncogene tyrosine protein kinase src , stereochemistry , ic50 , potency , inhibitory postsynaptic potential , structure–activity relationship , pharmacology , biochemistry , in vitro , endocrinology , medicine
A new class of 4‐oxo‐4 H ‐1‐benzopyran derivatives were synthesized and their antiproliferative activity examined against a panel of three human cancer cell lines, that is, breast carcinoma (MDA‐MB‐468), ovarian adenocarcinoma (SK‐OV‐3), and colorectal adenocarcinoma (HT‐29). Two compounds, that is, 3‐hexyl‐7,8‐dihydroxy‐4‐oxo‐4 H ‐1‐benzopyran and ( E )‐ethyl 3‐(7‐methoxy‐4‐oxo‐4 H ‐1‐benzopyran‐3‐yl)acrylate were found to be potent against all three cancer cell lines studied at 50 μM concentration. Also, the inhibitory potency of the compounds was evaluated against active Src kinase. A few of these compounds exhibited modest Src kinase inhibitory activity (IC 50 = 52–57 μM). Structure‐activity relationship studies with respect to the nature and position of substituents on the lead compounds could be further exploited for the design and development of more potent antiproliferative agents and/or Src kinase inhibitors.