Synthesis, antiproliferative, and c-Src kinase inhibitory activities of 4-oxo-4H-1-benzopyran derivatives

Karam Chand, Rakesh K. Tiwari, Sumit Kumar, Amir Nasrolahi Shirazi, Sweta Sharma, Erik V. Van Der Eycken, Virinder S. Parmar, Keykavous Parang, Sunil K. Sharma

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Abstract

A new class of 4-oxo-4H-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-4H-1-benzopyran and (E)-ethyl 3-(7-methoxy-4-oxo-4H-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 (IC50 = 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.

Original languageEnglish (US)
Pages (from-to)562-572
Number of pages11
JournalJournal of Heterocyclic Chemistry
Volume52
Issue number2
DOIs
StatePublished - 2015
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Chand, K., Tiwari, R. K., Kumar, S., Shirazi, A. N., Sharma, S., Van Der Eycken, E. V., Parmar, V. S., Parang, K., & Sharma, S. K. (2015). Synthesis, antiproliferative, and c-Src kinase inhibitory activities of 4-oxo-4H-1-benzopyran derivatives. Journal of Heterocyclic Chemistry, 52(2), 562-572. https://doi.org/10.1002/jhet.2106