Abstract
Two series of new 5-benzylidenethiazolidine-2,4-diones bearing benzenesulfonamide moiety were designed and synthesized. The synthesized compounds were evaluated for several biological activities, including cytotoxicity, histone deacetylation, and protein phosphatase 1B (PTP1B) inhibitory effects. It was found that those 5-benzylidenethiazolidine-2,4-diones with a chlorine substituent on the benzenesulfonamide moiety exhibited significant cytotoxicity, comparable to that of SAHA, which was used as a positive control. Several cytotoxic compounds also exhibited inhibitory effects against histone deacetylation, suggesting that these compounds might possess histone deacetylase inhibitory property. On the activity of PTP1B, however, these compounds displayed insignificant inhibitory effects.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Alegaon SG, Alagawadi KR (2012) New thiazolidine-2, 4-diones as antimicrobial and cytotoxic agent. Med Chem Res 21:3214–3223
Aneja DK, Lohan P, Arora S, Sharma C, Aneja KR, Prakash O (2011) Synthesis of new pyrazolyl-2, 4-thiazolidinediones as antibacterial and antifungal agents. Org Med Chem Lett 1:15–19
Baba S (2001) Pioglitazone: a review of Japanese clinical studies. Curr Med Res Opin 17:166–189
Barros FW, Silva TG, da Rocha Pitta MG, Bezerra DP, Costa-Lotufo LV, de Moraes MO, Pessoa C, de Moura MA, de Abreu FC, de Lima Mdo C, Galdino SL, Pitta Ida R, Goulart MO (2012) Synthesis and cytotoxic activity of new acridine-thiazolidine derivatives. Bioorg Med Chem 20:3533–3539
Bhattarai BR, Kafle B, Hwang JS, Ham SW, Lee KH, Park H, Han IO, Cho H (2010) Novel thiazolidinedione derivatives with anti-obesity effects: dual action as PTP1B inhibitors and PPAR-γ activators. Bioorg Med Chem Lett 20:6758–6763
Bozdağ-Dündar O, Ozgen O, Menteşe A, Altanlar N, Atli O, Kendi E, Ertan R (2007) Synthesis and antimicrobial activity of some new thiazolyl thiazolidine-2,4-dione derivatives. Bioorg Med Chem 15:6012–6017
Bruno G, Costantino L, Curinga C, Maccari R, Monforte F, Nicoló F, Ottanà R, Vigorita MG (2002) Synthesis and aldose reductase inhibitory activity of 5-aryliden-2, 4-thiazolidinediones. Bioorg Med Chem 10:1077–1084
Cheng-Lai A, Levine A (2000) Rosiglitazone: an agent from the thiazolidinedione class for the treatment of type 2 diabetes. Heart Dis 2:326–333
da Rocha Junior LF, Rêgo MJ, Cavalcanti MB, Pereira MC, Pitta MG, de Oliveira PS, Gonçalves SM, Duarte AL, de Lima Mdo C, Pitta Ida R, Pitta MG (2013) Synthesis of novel thiazolidinedione and evaluation of its modulatory effect on IFN-γ, IL-6, IL-17A, and IL-22 production in PBMCs from rheumatoid arthritis patients. Biomed Res Int 2013:926060
Desai NC, Satodiya HM, Kotadiya GM, Vaghani HV (2014) Synthesis and antibacterial and cytotoxic activities of new N-3 substituted thiazolidine-2,4-dione derivatives bearing the pyrazole moiety. Arch Pharm (Weinheim). doi:10.1002/ardp.201300466
Jain VS, Vora DK, Ramaa CS (2013) Thiazolidine-2,4-diones: progress towards multifarious applications. Bioorg Med Chem 21:1599–1620
Kim Y, You YJ, Nam NH, Ahn BZ (2002) Prodrugs of 4′-demethyl-4-deoxypodophyllotoxin: synthesis and evaluation of the antitumor activity. Bioorg Med Chem Lett 12:3435–3438
Lauffer BE, Mintzer R, Fong R, Mukund S, Tam C, Zilberleyb I, Flicke B, Ritscher A, Fedorowicz G, Vallero R, Ortwine DF, Gunzner J, Modrusan Z, Neumann L, Koth CM, Lupardus PJ, Kaminker JS, Heise CE, Steiner P (2013) Histone deacetylase (HDAC) inhibitor kinetic rate constants correlate with cellular histone acetylation but not transcription and cell viability. J Biol Chem 288:26926–26943
Maccari R, Paoli P, Ottanà R, Jacomelli M, Ciurleo R, Manao G, Steindl T, Langer T, Vigorita MG, Camici G (2007) 5-Arylidene-2,4-thiazolidinediones as inhibitors of protein tyrosine phosphatases. Bioorg Med Chem 15:5137–5149
Menteşe A, Ceylan-Unlüsoy M, Bozdağ-Dündar O, Altanlar N, Ertan R (2009) Synthesis and antimicrobial activity of some novel thiazolidine-2,4-dione derivatives. Arzneimittelforschung 59:659–665
Mohan R, Sharma AK, Gupta S, Ramaa CS (2012) Design, synthesis, and biological evaluation of novel 2,4-thiazolidinedione derivatives as histone deacetylase inhibitors targeting liver cancer cell line. Med Chem Res 21:1156–1165
Nam NH, Huong TL, do Dung TM, Dung PT, Oanh DT, Quyen D, le Thao T, Park SH, Kim KR, Han BW, Yun J, Kang JS, Kim Y, Han SB (2013) Novel isatin-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents. Eur J Med Chem 70:477–486
Nastasă C, Tiperciuc B, Pârvu A, Duma M, Ionuţ I, Oniga O (2013) Synthesis of new N-substituted 5-arylidene-2,4-thiazolidinediones as anti-inflammatory and antimicrobial agents. Arch Pharm (Weinheim) 346:481–490
Oanh DT, Hai HV, Park SH, Kim HJ, Han BW, Kim HS, Hong JT, Han SB, Hue VT, Nam NH (2011) Benzothiazole-containing hydroxamic acids as histone deacetylase inhibitors and antitumor agents. Bioorg Med Chem Lett 21:7509–7512
Patel J, Anderson RJ, Rappaport EB (1999) Rosiglitazone monotherapy improves glycaemic control in patients with type 2 diabetes: a twelve-week, randomized, placebo-controlled study. Diabetes Obes Metab 1:165–172
Romagnoli R, Baraldi PG, Salvador MK, Camacho ME, Balzarini J, Bermejo J, Estévez F (2013) Anticancer activity of novel hybrid molecules containing 5-benzylidene thiazolidine-2,4-dione. Eur J Med Chem 63:44–57
Schuttelkopf AW, van Aalten DM (2004) PRODRG: a tool for high-throughput crystallography of protein-ligand complexes. Acta crystallogr Sect D Biol Crystallogr 60:1355–1363
Skehan P, Storeng R, Scudiero D, Monk A, MacMahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR (1990) New colorimetric cytotoxicity assay for anticancer drug screening. J Natl Cancer Inst 82:1107–1112
Somoza JR, Skene RJ, Katz BA, Mol C, Ho JD, Jennings AJ, Luong C, Arvai A, Buggy JJ, Chi E, Tang J, Sang BC, Verner E, Wynands R, Leahy EM, Dougan DR, Snell S, Navre M, Knuth MW, Swanson RV, McRee DE, Tari LW (2004) Structural snapshots of human HDAC8 provide insights into the class I histone deacetylases. Structure 12:1325–1334
Trott O, Olson AJ (2010) AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 31:455–461
Tung TT, Oanh DT, Dung PT, Hue VT, Park SH, Han BW, Kim Y, Hong JT, Han SB, Nam NH (2013) New benzothiazole/thiazole-containing hydroxamic acids as potent histone deacetylase inhibitors and antitumor agents. Med Chem 9:1051–1057
Wu L, Smythe AM, Stinson SF, Mullendore LA, Monks A, Scudiero DA, Paull KD, Koutsoukos AD, Rubinstein LV, Boyd MR, Shoemaker RH (1992) Multidrug-resistant phenotype of disease-oriented panels of human tumor cell lines used for anticancer drug screening. Cancer Res 52:3029–3034
You YJ, Kim Y, Nam NH, Bang SC, Ahn BZ (2004) Alkyl and carboxylalkyl esters of 4′-demethyl-4-deoxypodophyllotoxin: synthesis, cytotoxic, and antitumor activity. Eur J Med Chem 39:189–193
Acknowledgments
We acknowledge the principal financial supports from the National Foundation for Science and Technology of Vietnam (NAFOSTED, Grant number 104.01-2014.11). The biological study was supported by the Medical Research Center program (MRC, Grant number 2010-0029480).
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Thuan, N.T., Dung, D.T.M., Que, D.N. et al. Synthesis and bioevaluation of new 5-benzylidenethiazolidine-2,4-diones bearing benzenesulfonamide moiety. Med Chem Res 24, 3803–3812 (2015). https://doi.org/10.1007/s00044-015-1422-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00044-015-1422-9