Synthesis and in vitro antiproliferative activity against human cancer cell lines of novel 5-(4-methyl-benzylidene)-thiazolidine-2,4-diones

Abstract

A series of novel 5-(4-methyl-benzylidene)-thiazolidine-2,4-dione derivatives 6 (a-d) and 7 (a-g) were synthesized with different substituted aromatic sulfonyl chlorides (R-SO(2)-Cl) and alkyl halides (R-X) and were characterized by (1)H NMR, LC/MS, FTIR and elemental analyses. All the compounds synthesised were evaluated for their cell antiproliferation activity by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. The antiproliferative effects of the synthesised compounds were tested against viable human skin fibroblast cell line and carcinoma cell lines namely HeLa cells, HT-29 cells, MCF-7 cells, HepG-2 cells by adopting positive and negative control. The importance of the nitro group on thiazolidinone moiety was confirmed and it was concluded that the fourth position of the substituted aryl ring plays a dominant role and was responsible for the antiproliferative activity. Among the synthesized compounds only 6a, 7e and 7g have potent antiproliferative activity on all the carcinoma cell lines tested.

Synthesis and in vitro cytotoxic evaluation of novel diazaspiro bicyclo hydantoin derivatives in human leukemia cells: A SAR study

“…Recently, we have investigated the synthesis of bioactive heterocycles and evaluation of their antiproliferative activity against different carcinoma cell lines [15,16]. Our investigation on the synthesis of different substituted diazaspiro hydantoin derivatives and evaluation of their antitumor activities unraveled that the fluorine substituted hydantoin analogs possessed potent antitumor activity [16].…”

Diacetoxyiodobenzene mediated oxidative dethionation of N-substituted-5-arylmethylidene rhodanines: an efficient synthesis of N-substituted-5-arylmethylidene thiazolidine-2,4-diones

“…Moreover, N-substituted 5-arylmethylidene thiazolidine-2,4-diones are also prepared by alkylation of 5-arylmethylidene rhodanine with alkyl halide in presence of base. 15,16 However, the conversion of thioxo group in N-substituted-5-arylmethylidene rhodanines into their corresponding oxo analogue has never been realized using hypervalent iodine compounds.…”

Synthesis and antimicrobial activities of some new 5-((3-(aryl)-1-phenyl-1H-pyrazol-4-yl)methylene)-3-phenylthiazolidine-2,4-diones

“…Diverse biological activities, namely, antihyperglycemic (Lee et al, 2005), bactericidal (Mahalle et al, 2008;Bozdag-Dundar et al, 2008a, b), pesticidal (Hyo et al, 2007), fungicidal (Deohate et al, 2004), insecticidal (Sahu et al, 2007), anticonvulsant (Altintas et al, 2006), tuberculostatic (Thaker et al, 2003), anti-inflammatory (Szeto and Li, 2008;Pastromas et al, 2008;Murugan et al, 2009;Cioni and Ramelli, 2009;Sha et al, 2009), antithyroid and potentiation of pentobarbital induced sleeping time, etc., have been associated with thiazolidinone derivatives. Different possibilities of heterocyclic modifications (Bozdag-Dundar et al, 2008a, b) with a wide spectrum of pharmacological properties are the most important grounds for investigation of this class of compounds (Jeon et al, 2006;Chandrappa et al, 2008;Ramesh et al, 2004;Clark et al, 1991;Altanlar, 1999, 2006). The fifth position of thiazolidine-2, 4-diones (the active methylene group) being relatively more reactive, hence most of the modification at this position exhibit a wide spectrum of pharmacological properties.…”