Studies on the synthetic and structural aspects of benzosuberones bearing 2, 4-thiazolidenone moiety as potential anti-cancer agents

Eur J Med Chem. 2014 Jan:71:91-7. doi: 10.1016/j.ejmech.2013.10.078.

Lingaiah Nagarapu ¹, Bandi Yadagiri ², Rajashaker Bantu ², C Ganesh Kumar ³, Sujitha Pombala ³, Jagadesh Nanubolu ⁴

Affiliations

1 Organic Chemistry Division II, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, Andhra Pradesh, India. Electronic address: lnagarapuiict@yahoo.com.
2 Organic Chemistry Division II, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, Andhra Pradesh, India.
3 Centre for Medicinal Chemistry & Pharmacology, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
4 Centre for X-Ray Crystallography, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.

PMID: 24287557 DOI: 10.1016/j.ejmech.2013.10.078

Abstract

Novel representative of the important group of biologically active benzosuberones bearing 2, 4-thiazolidenone moiety was synthesized as potential Anticancer agents (6a-j). These compounds were synthesized in good yields from Knoevenagel condensation of compounds 2a-b with thiazolidenone derivatives 3a-e in the presence of sodium acetate and glacial acetic acid. The in vitro cytotoxicity of these compounds was evaluated against different human Cancer cell lines (A549, HeLa, MDA-MB-231, MCF-7) and normal cell line, HEK293. Compound 6a exhibited promising cytotoxicity with IC₅₀ values ranging from 2.98 to 13.34 μM against all the tested Cancer cell lines, HeLa, A549, MCF-7 and MDA-MB-231, while compound 6g showed potent cytotoxicity against human breast adenocarcinoma cell line (MCF-7, IC₅₀ value of 1.91 μM).

Keywords

2, 4-Thiazolidenone; Benzosuberone; Cytotoxicity; Knoevenagel condensation; Vilsmeier Haack Arnold reaction.

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