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: [email protected].
  • 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.
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.