Abstract
There are limited studies centring on the potential of thiazolidin-4-ones as anticancer agents. In this study, a new series of 2-(3-substituted-1H-pyrazol-4-yl)-3-(3-substituted-5-sulfanyl-1,2,4-triazol-4-yl)-1,3-thiazolidin-4-one (4a–o) have been synthesized by cyclo-condensation reaction of 5-substituted-4-[(3-substituted-1H-pyrazol-4-ylmethylidene)amino]-2H-1,2,4-triazole-3-thione (3a–o) and thioglycolic acid. The structures of all the synthesized compounds were confirmed by elemental analysis, spectral techniques like IR, 1H NMR, and mass spectroscopy. Few compounds exhibited dose-dependent cytotoxic effect in MTT assay in human breast cancer (MCF-7) cells. Apoptotic degradation of DNA due to action of potent thiazolidin-4-ones was analysed by agarose gel electrophoresis and visualized by ethidium bromide staining (comet assay). A concentration-dependent increase in tail length and olive tail moment was observed when treated with thiazolidin-4-ones. In vitro antioxidant studies like DPPH and ABTS-free radical scavenging assays-indicated moderate activity of thiazolidin-4-ones.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Amir M, Azam F (2004) Synthesis and biological evaluation of some 4-thiazolidinones. Indian J Heterocycl Chem 14:119–122
Bandgar PB, Gawande SS, Bodade RG, Gawande NM, Khobragade CN (2009) Synthesis and biological evaluation of a novel series of pyrazole chalcones as anti-inflammatory, antioxidant and antimicrobial agents. Bioorg Med Chem 17:8168–8173
Bandgar PB, Gawande SS, Bodade RG, Totre JV, Khobragade CN (2010) Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents. Bioorg Med Chem 18:1364–1370
Brueggemeier RW, John CH, Edgar SD (2004) Aromatase inhibitors in the treatment of breast cancer. Endocrine Rev 26:331–345
Chandrakantha B, Isloor AM, Shetty P, Isloor S, Malladi S, Fun HK (2011) Synthesis, characterization and antimicrobial activity of novel ethyl 1-(N-substituted)-5-phenyl-1H-pyrazole-4-carboxylate derivatives. Med Chem Res. doi:10.1007/s00044-011-9796-9
Demirbas N, Karaoglu SA, Demirbas A, Sanack K (2004) Synthesis and antimicrobial activities of some new 1-(5-phenylamino-[1,3,4]thiadiazol-2-yl)methyl-5-oxo-[1,2,4]triazole and 1-(4-phenyl-5-thioxo-[1,2,4] triazole-3-yl)methyl-5-oxo[1,2,4]triazole derivatives. Eur J Med Chem 39:793–804
Dobrowsky W, Huigol NG, Jayatilake RS, Kizilbash NI, Okkan S, Kagiya TV, Tatsuzaki H (2005) AK-2123 (Sanazol) as a radiation sensitizer in the treatment of stage III cancer cervix: initial results of an IAEA multicentre randomized trial. J Cancer Res Ther 1:75–78
Hafez HN, El-Gazzar ABA (2009) Synthesis and antitumor activity of substituted triazolo[4,3-a]pyrimidin-6-sulfonamide with an incorporated thiazolidinone moiety. Bioorg Med Chem Lett 19:4143–4147
Holla BS, Poojary KN, Rao BS, Shivananda MK (2002) New bis-aminomercaptotriazoles and bis-triazolothiadiazoles as possible anticancer agents. Eur J Med Chem 37:511–517
Ibrahim DA (2009) Synthesis and biological evaluation of 3,6-disubstituted [1,2,4] triazolo[3,4-b][1,3,4]thiadiazole derivatives as a novel class of potential anti-tumor agents. Eur J Med Chem 44:2776–2781
Isloor AM, Kalluraya B, Shetty P (2009) Regioselective reaction: synthesis, characterization and pharmacological studies of some new Mannich bases derived from 1,2,4-triazoles. Eur J Med Chem 44:3784–3787
Kavitha CV, Nambiar M, Ananda Kumar CS, Choudhari B, Muniyappa K, Rangappa KS, Raghavan SC (2009) Novel derivatives of spirohydantoin induce growth inhibition followed by apoptosis in leukemia cells. Biochem Pharmacol 77:348–363
Lee T, Lau T, Ng I (2002) Doxorubicin-induced apoptosis and chemosensitivity in hepatoma cell lines. Cancer Chemother Pharmacol 49:78–86
Malladi S, Isloor AM, Isloor S, Akhila DS (2011a) Synthesis, characterization and ntibacterial activity of some new pyrazole based Schiff bases. Arabian J Chem. doi:10.1016/j.arabjc.2011.10.009
Malladi S, Isloor AM, Shetty P, Fun HK, Telkar S, Mahmood R, Isloor N (2011b) Synthesis and anti-inflammatory evaluation of some new 3,6-disubstituted-1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazoles bearing pyrazole moiety. Med Chem Res. doi:10.1007/s00044-011-9865-0
Mathew V, Keshavayya J, Vaidya VP, Giles D (2007) Studies on synthesis and pharmacological activities of 3,6-disubstituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and their dihydro analogues. Eur J Med Chem 42:823–840
Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxic assays. Immunol Methods 65:55–63
Padmavathi V, Reddy GS, Padmaja A, Kondaiah P, Ali-Shazia (2009) Synthesis, antimicrobial and cytotoxic activities of 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles. Eur J Med Chem 44:2106–2112
Palekar VS, Damle AJ, Shukla SR (2009) Synthesis and antibacterial activity of some novel bis-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and bis-4-thiazolidinone derivatives from terephthalic dihydrazide. Eur J Med Chem 44:5112–5116
Porter P (2008) Westernizing women’s risks? Breast cancer in lower-income countries. N Engl J Med 358:213–216
Selvi G, Rajendran SP (2007) Synthesis of 2-[3′(2′-chloroquinolinyl)-3-carbethoxymethyl]-4-thiazolidinones. Indian J Het Chem 17:201–202
Siddiqui N, Deepanjali, Md Arshad F, Rana A (2007) Synthesis and anticonvulsant screening of 2-(substituted aryl)-3-(4H-1,2,4-triazol-4-yl)-1,3-thiazolidinon-4-ones. Indian J Het Chem 16:403–404
Singh NP (2000) Microgels for estimation of DNA strand breaks, DNA protein cross links and apoptosis. Mutation Res 455:111–127
Sreejayan N, Rao MN (1996) Free radical scavenging activity of curcuminoids. Drug Res 46:169–171
Sunil D, Isloor AM, Shetty P, Chandrakantha B, Satyamoorthy K (2011) Synthesis, characterization and in vitro cytotoxic properties of some new Schiff and Mannich bases in Hep G2 cells. Med Chem Res 20:1024–1032
Swamy SN, Basappa, Priya BS, Prabhuswamy B, Doreswamy BH, Prasad JS, Rangappa KS (2006) Synthesis of pharmaceutically important condensed heterocyclic 4,6-disubstituted-1,2,4-triazolo-1,3,4-thiadiazole derivatives as antimicrobials. Eur J Med Chem 41:531–538
Vaijanathappa J, Badami S, Bhojraj S (2008) In vitro antioxidant activity of Enicostemmaaxillare. J Health Sci 54:524–528
Vijesh AM, Isloor AM, Prabhu V, Ahmad S, Malladi S (2010) Synthesis, characterization and anti-microbial studies of some novel 2,4-disubstituted thiazoles. Eur J Med Chem 45:5460–5464
Vijesh AM, Isloor AM, Telkar S, Peethambar SK, Rai S, Isloor N (2011a) Synthesis, characterization and antimicrobial studies of some new pyrazole incorporated imidazole derivatives. Eur J Med Chem 46:3531–3536
Vijesh AM, Isloor AM, Peethambar SK, Shivananda KN, Arulmoli T, Isloor NA (2011b) Hantzsch reaction: synthesis and characterization of some new 1,4-dihydropyridine derivatives as potent antimicrobial and antioxidant agents. Eur J Med Chem 46:5591–5597
Wilson C, Gomes CRB, Vellasco WT (2008) Chemistry and biological activities of 1,3-thiazolidin-4-ones. Mini-Rev Org Chem 5:336–344
Acknowledgments
The authors are thankful to the Head-SIF, Indian Institute of Science, Bangalore for providing NMR and mass spectral data. AMI is thanks Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India for the ‘Young Scientist’ award.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Isloor, A.M., Sunil, D., Shetty, P. et al. Synthesis, characterization, anticancer, and antioxidant activity of some new thiazolidin-4-ones in MCF-7 cells. Med Chem Res 22, 758–767 (2013). https://doi.org/10.1007/s00044-012-0071-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00044-012-0071-5