ORIGINAL RESEARCH Synthesis, characterization, and biological evaluation of thiazolidine-2,4-dione derivatives Shankar G. Alegaon • Kallanagouda R. Alagawadi • Sneha M. Pawar • D. Vinod • Udaysingh Rajput Received: 26 April 2013 / Accepted: 8 August 2013 / Published online: 21 August 2013 Ó Springer Science+Business Media New York 2013 Abstract As a part of our continuation studies in devel- oping new derivatives as dual antimicrobial/antitumor agents we describe the synthesis of new (Z)-2-(5-arylidene- 2,4-dioxothiazolidin-3-yl) acetic acid derivatives (3a–m). The chemical structures of the compound were elucidated by FTIR, 1 H NMR, 13 C NMR, and elemental analysis data. The antimicrobial activity of all products was examined. All newly synthesized compounds were tested for their in vitro anticancer activity against four cancer cell lines. Among the synthesized compounds, 3a exhibited notable activity against HeLa, HT29, A549, and MCF-7 cell lines with IC 50 values of 55, 40, 38, and 50 lM, respectively. In order to predict the drug likeliness of the synthesized compounds on the guidelines of Lipinski rule of five studies was carried out using Pallas software. Keywords Antimicrobial activity Á Cytotoxic activity Á Thiazolidine-2,4-dione Á Drug likeliness Introduction The development of novel antimicrobial and anticancer therapeutic agents is one of the fundamental goals in medicinal chemistry. Despite major breakthroughs in many areas of modern medicine, significant rise in multi-drug resistant microbial infections and cancer has become an economic as well as a serious health care problem. In some microbial infections, strains of microbes have become resistant to all available drugs. There is an increasing need for new medicinal organic agent because a dose of anticancer drug sufficient to kill cancer cells is often lethal to the normal tissue and leads to many side effects, which in turn, limits its treatment efficacy (Aydemir and Bilaloglu, 2003). The thi- azolidine-2,4-dione (TZDs) is an imperative scaffold that is not only synthetically important but also possesses a wide range of promising biological activities. The TZDs moiety is extensively utilized as a carboxylic acid mimetic to improve the metabolic stability and therapeutic profile of bioactive agents (Boyd, 2007; McIntyre et al., 2007; Elte and Blickle, 2007). During recent years there has been a large investi- gation on different classes of TZDs compounds, many of these are known to possess antibacterial and antifungal (Ayhan-Kilcigil and Altanlar, 2000; Heerding et al., 2003; Bozdag-Dundar et al., 2007; Tuncbilek and Altanlar, 2006) properties. In addition, this class of compounds has several other potentially beneficial effects including on lipid profile, blood pressure lowering, and anti-inflammatory effects (Kalaitzidis et al., 2009). TZDs target vascular cells (Kure- bayashi et al., 2005) and monocytes/macrophages (Jiang et al., 1998; Ricote et al., 1998) to inhibit the production of pro-inflammatory cytokines as well as the expression of inducible nitric oxide synthase and cell adhesion molecules. These drugs may also be beneficial in multiple sclerosis and neurodegenerative diseases, including Alzheimer’s and Electronic supplementary material The online version of this article (doi:10.1007/s00044-013-0705-2) contains supplementary material, which is available to authorized users. S. G. Alegaon (&) Á K. R. Alagawadi Á S. M. Pawar Department of Pharmaceutical Chemistry, KLE University’s College of Pharmacy, Nehrunagar, Belgaum 590010, Karnataka, India e-mail: sgalegaon@gmail.com; sgalegaon@klepharm.edu D. Vinod Department of Pharmaceutical Chemistry, College of Pharmacy, Madras Medical College, Chennai, Tamil Nadu, India U. Rajput Department of Chemistry, R. L. Science Institute, College Road, Belgaum 590001, Karnataka, India 123 Med Chem Res (2014) 23:987–994 DOI 10.1007/s00044-013-0705-2 MEDICINAL CHEMISTR Y RESEARCH