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Mini-Reviews in Medicinal Chemistry

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ISSN (Print): 1389-5575
ISSN (Online): 1875-5607

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Review Article

Chemical Synthesis, Mechanism of Action and Anticancer Potential of Medicinally Important Thiazolidin-2,4-dione Derivatives: A Review

Author(s): Harsh Kumar, Aakash Deep* and Rakesh Kumar Marwaha*

Volume 19, Issue 18, 2019

Page: [1474 - 1516] Pages: 43

DOI: 10.2174/1389557519666190513093618

Price: $65

Abstract

Thiazolidin-2,4-dione (TZD) possessing an active methylene constitute an important chemical class of compounds for the development of new drugs. So, many scholars have synthesized these derivatives as target molecules and evaluated their biological potential. Currently, some of the TZDs are synthesized to treat human cancers stating high levels of PPARγ because it is expected that activation of PPARγ arbitrates their anticancer activity because PPARγ ligands have recently been established to affect differentiation, cell proliferation and apoptosis of different cell types. In the present review, the synthesis of various derivatives of thiazolidine-2,4-diones, their mechanism of action and anticancer activity have been highlighted.

Keywords: Anticancer, thiazolidin-2, 4-dione, PPARγ, chemical synthesis, thiazolidin-2, 4-diones (TZDs).

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[1]
Parekh, N.M.; Juddhawala, K.V.; Rawal, B.M. Antimicrobial activity of thiazolyl benzenesulfonamide-condensed 2,4-thiazolidinediones derivatives. Med. Chem. Res., 2013, 22(6), 2737-2745.
[http://dx.doi.org/10.1007/s00044-012-0273-x]
[2]
Asati, V.; Mahapatra, D.K.; Bharti, S.K. Thiazolidine-2,4-diones as multi-targeted scaffold in medicinal chemistry: Potential anticancer agents. Eur. J. Med. Chem., 2014, 87(1), 814-833.
[http://dx.doi.org/10.1016/j.ejmech.2014.10.025] [PMID: 25440883]
[3]
Grillier-Vuissoz, I.; Mazerbourg, S.; Boisbrun, M.; Kuntz, S.; Chapleur, Y.; Flament, S. PPARγ-independent activity of thiazolidinediones: A promising mechanism of action for new anticancer drugs. J. Carcinogene. Mutagene , 2012, S8. 002
[http://dx.doi.org/10.4172/2157-2518.S8-002]
[4]
Palkar, M.B.; Jalalpure, S.S.; Rane, R.A.; Patel, H.M.; Shaikh, M.S.; Hampannavar, G.A.; Alwan, W.S.; Bolakatti, G.S.; Karpoormath, R. Novel series of coumarinyl substituted-thiazolidin-2,4-dione analogs as anticancer agents: Design, synthesis, spectral studies and cytotoxicity evaluation. Anticancer. Agents Med. Chem., 2015, 15(8), 970-979.
[http://dx.doi.org/10.2174/1871520615666150424110339] [PMID: 25909852]
[5]
Desai, N.C.; Satodiya, H.M.; Rajpara, K.M.; Joshi, V.V.; Bhatt, K.; Vaghani, H.V. Synthesis and evaluation of N-substituted thiazolidine-2,4-dione containing pyrazole as potent antimicrobial agents. Antiinfect. Agents, 2014, 12(1), 85-94.
[http://dx.doi.org/10.2174/22113525113119990117]
[6]
Patil, V.; Tilekar, K.; Mehendale-Munj, S.; Mohan, R.; Ramaa, C.S. Synthesis and primary cytotoxicity evaluation of new 5-benzylidene-2,4-thiazolidinedione derivatives. Eur. J. Med. Chem., 2010, 45(10), 4539-4544.
[http://dx.doi.org/10.1016/j.ejmech.2010.07.014] [PMID: 20667627]
[7]
Blanquicett, C.; Roman, J.; Hart, C. M. Thiazolidinediones as anti-cancer agents. Cancer Ther , 2008, 6(A), 25.
[8]
Dai, Y.; Wang, W.H. Peroxisome proliferator-activated receptor γ and colorectal cancer. World J. Gastrointest. Oncol., 2010, 2(3), 159-164.
[http://dx.doi.org/10.4251/wjgo.v2.i3.159] [PMID: 21160824]
[9]
Cesario, R.M.; Stone, J.; Yen, W.C.; Bissonnette, R.P.; Lamph, W.W. Differentiation and growth inhibition mediated via the RXR: PPARgamma heterodimer in colon cancer. Cancer Lett., 2006, 240(2), 225-233.
[http://dx.doi.org/10.1016/j.canlet.2005.09.010] [PMID: 16271436]
[10]
Bozic, B.; Rogan, J.; Poleti, D.; Rancic, M.; Trisovic, N.; Bozic, B.; Uscumlic, G. Synthesis, characterization and biological activity of 2-(5-arylidene-2,4-dioxotetrahydrothiazole-3-yl)propanoic acid derivatives. Arab. J. Chem., 2017, 10, S2637-S2643.
[http://dx.doi.org/10.1016/j.arabjc.2013.10.002]
[11]
Chinthala, Y.; Kumar Domatti, A.; Sarfaraz, A.; Singh, S.P.; Kumar Arigari, N.; Gupta, N.; Satya, S.K.V.N.; Kotesh Kumar, J.; Khan, F.; Tiwari, A.K.; Paramjit, G. Synthesis, biological evaluation and molecular modeling studies of some novel thiazolidinediones with triazole ring. Eur. J. Med. Chem., 2013, 70, 308-314.
[http://dx.doi.org/10.1016/j.ejmech.2013.10.005] [PMID: 24177357]
[12]
Kaminskyy, D.; Zimenkovsky, B.; Lesyk, R. Synthesis and in vitro anticancer activity of 2,4-azolidinedione-acetic acids derivatives. Eur. J. Med. Chem., 2009, 44(9), 3627-3636.
[http://dx.doi.org/10.1016/j.ejmech.2009.02.023] [PMID: 19299038]
[13]
Barros, F.W.A.; Silva, T.G.; da Rocha Pitta, M.G.; Bezerra, D.P.; Costa-Lotufo, L.V.; de Moraes, M.O.; Pessoa, C.; de Moura, M.A.; de Abreu, F.C. de Lima, Mdo.C.; Galdino, S.L.; Pitta, Ida.R.; Goulart, M.O.F. Synthesis and cytotoxic activity of new acridine-thiazolidine derivatives. Bioorg. Med. Chem., 2012, 20(11), 3533-3539.
[http://dx.doi.org/10.1016/j.bmc.2012.04.007] [PMID: 22546208]
[14]
Rego, M.J.B.D.M.; Pitta, M.R.G.; Pereira, D.T.M.; Silva, J.C.D.; Rabello, M.M.; Lima, M.D.C.A.D.; Hernandes, M.Z.; Pitta, I.D.R.; Galdino, S.L.; Pitta, M.G.D.R. Synthesis, in vitro anticancer activity and in silico study of new disubstituted thiazolidinedione derivatives. Med. Chem. Res., 2014, 23, 3220-3226.
[http://dx.doi.org/10.1007/s00044-013-0902-z]
[15]
Nagarapu, L.; Yadagiri, B.; Bantu, R.; Kumar, C.G.; Pombala, S.; Nanubolu, J. Studies on the synthetic and structural aspects of benzosuberones bearing 2, 4-thiazolidenone moiety as potential anti-cancer agents. Eur. J. Med. Chem., 2014, 71, 91-97.
[http://dx.doi.org/10.1016/j.ejmech.2013.10.078] [PMID: 24287557]
[16]
Kumar, K.S.; Reddy, B.M.; Babu, V.H. Synthesis of some novel 2, 4-thiazolidinedione incorporated pyrazole derivatives as anti-cancer agents. Int. J. Pharm. Pharm. Sci., 2014, 6(2), 831-834.
[17]
Prakash, O.; Aneja, D.K.; Arora, S.; Sharma, C.; Aneja, K.R. Synthesis and antimicrobial activities of some new 5-((3-(aryl)-1-phenyl-1H-pyrazol-4-yl)methylene)-3-phenylthiazolidine-2,4-diones. Med. Chem. Res., 2012, 21, 10-15.
[http://dx.doi.org/10.1007/s00044-010-9503-2]
[18]
Sunduru, N.; Srivastava, K.; Rajakumar, S.; Puri, S.K.; Saxena, J.K.; Chauhan, P.M.S. Synthesis of novel thiourea, thiazolidinedione and thioparabanic acid derivatives of 4-aminoquinoline as potent antimalarials. Bioorg. Med. Chem. Lett., 2009, 19(9), 2570-2573.
[http://dx.doi.org/10.1016/j.bmcl.2009.03.026] [PMID: 19339178]
[19]
Ponnuchamy, S.; Kanchithalaivan, S.; Ranjith Kumar, R.; Ali, M.A.; Choon, T.S. Antimycobacterial evaluation of novel hybrid arylidene thiazolidine-2,4-diones. Bioorg. Med. Chem. Lett., 2014, 24(4), 1089-1093.
[http://dx.doi.org/10.1016/j.bmcl.2014.01.007] [PMID: 24472146]
[20]
Lobo, P.L.; Poojary, B.; Manjunatha, K.; Prathibha, A.; Kumari, N.S. Novel thiazolidine-2,4-dione mannich bases: Synthesis, characterization and antimicrobial activity. Pharma Chem., 2012, 4(3), 867-871.
[21]
Patel, N.B.; Purohit, A.C.; Rajani, D. Newer thiazolopyrimidine-based sulfonamides clubbed with benzothiazole moiety: Synthesis and biological evaluation. Med. Chem. Res., 2014, 23, 4789-4802.
[http://dx.doi.org/10.1007/s00044-014-1052-7]
[22]
Shaikh, F.M.; Patel, N.B.; Sanna, G.; Busonera, B.; Colla, P.L.; Rajani, D.P. Synthesis of some new 2-amino-6-thiocyanato benzothiazole derivatives bearing 2,4-thiazolidinediones and screening of their in vitro antimicrobial, antitubercular and antiviral activities. Med. Chem. Res., 2015, 24, 3129-3142.
[http://dx.doi.org/10.1007/s00044-015-1358-0]
[23]
Sindhu, J.; Singh, H.; Khurana, J.M.; Sharma, C.; Aneja, K.R. Multicomponent domino process for the synthesis of some novel 5-(arylidene)-3-((1-aryl-1H-1,2,3-triazol-4-yl)methyl)-thiazolidine-2,4-diones using PEG-400 as an efficient reaction medium and their antimicrobial evaluation. Chin. Chem. Lett., 2015, 26, 50-54.
[http://dx.doi.org/10.1016/j.cclet.2014.09.006]
[24]
Malik, N.; Prasad, D.N. Synthesis and antimicrobial evaluation of N-substituted-5-benzylidene-2,4-thiazolidinedione derivatives. Iran. J. Pharm. Res., 2012, 8(3), 209-214.
[25]
Tunçbilek, M.; Altanlar, N. Synthesis and antimicrobial evaluation of some 3-(substituted phenacyl)-5-[4′-(4H-4-oxo-1-benzopyran-2-yl)-benzylidene]-2,4- thiazolidinediones. Farmaco, 1999, 54(7), 475-478.
[http://dx.doi.org/10.1016/S0014-827X(99)00054-3] [PMID: 10486915]
[26]
Juddhawala, K.V.; Parekh, N.M.; Rawal, B.M. Synthesis and antibacterial activities of N-chloro aryl acetamide substituted thaizole and 2,4-thazolidinedione derivatives. Arch. Appl. Sci. Res., 2011, 3(5), 540-548.
[27]
Bozdağ-Dündar, O.; Ozgen, O.; Menteşe, A.; Altanlar, N.; Atli, O.; Kendi, E.; Ertan, R. Synthesis and antimicrobial activity of some new thiazolyl thiazolidine-2,4-dione derivatives. Bioorg. Med. Chem., 2007, 15(18), 6012-6017.
[http://dx.doi.org/10.1016/j.bmc.2007.06.049] [PMID: 17618124]
[28]
Alegaon, S.G.; Alagawadi, K.R. New thiazolidine-2,4-diones as antimicrobial and cytotoxic agent. Med. Chem. Res., 2012, 21, 3214-3223.
[http://dx.doi.org/10.1007/s00044-011-9876-x]
[29]
Alegaon, S.G.; Alagawadi, K.R.; Pawar, S.M.; Vinod, D.; Rajput, U. Synthesis, characterization, and biological evaluation of thiazolidine-2,4-dione derivatives. Med. Chem. Res., 2014, 23, 987-994.
[http://dx.doi.org/10.1007/s00044-013-0705-2]
[30]
Datar, P.A.; Aher, S.B. Design and synthesis of novel thiazolidine-2,4-diones as hypoglycemic agents. J. Saudi Chem. Soc., 2016, 20, S196-S201.
[http://dx.doi.org/10.1016/j.jscs.2012.10.010]
[31]
da Costa Leite, L.F.; Veras Mourão, R.H. de Lima, Mdo.C.; Galdino, S.L.; Hernandes, M.Z.; de Assis Rocha Neves, F.; Vidal, S.; Barbe, J.; da Rocha Pitta, I. Synthesis, biological evaluation and molecular modeling studies of arylidene-thiazolidinediones with potential hypoglycemic and hypolipidemic activities. Eur. J. Med. Chem., 2007, 42(10), 1263-1271.
[http://dx.doi.org/10.1016/j.ejmech.2007.02.015] [PMID: 17448573]
[32]
Mishra, G.; Sachana, N.; Chawla, P. Synthesis and evaluation of thiazolidinedione-coumarin adducts as antidiabetic, anti-inflammatory and antioxidant agents. Lett. Org. Chem., 2015, 12, 429-445.
[http://dx.doi.org/10.2174/1570178612666150424235603]
[33]
Bozdağ-Dündar, O.; Evranos, B.; Daş-Evcimen, N.; Sarikaya, M.; Ertan, R. Synthesis and aldose reductase inhibitory activity of some new chromonyl-2,4-thiazolidinediones. Eur. J. Med. Chem., 2008, 43(11), 2412-2417.
[http://dx.doi.org/10.1016/j.ejmech.2008.01.004] [PMID: 18313804]
[34]
Bruno, G.; Costantino, L.; Curinga, C.; Maccari, R.; Monforte, F.; Nicoló, F.; Ottanà, R.; Vigorita, M.G. Synthesis and aldose reductase inhibitory activity of 5-arylidene-2,4-thiazolidinediones. Bioorg. Med. Chem., 2002, 10(4), 1077-1084.
[http://dx.doi.org/10.1016/S0968-0896(01)00366-2] [PMID: 11836118]
[35]
Kim, B.Y.; Ahn, J.B.; Lee, H.W.; Kang, S.K.; Lee, J.H.; Shin, J.S.; Ahn, S.K.; Hong, C.I.; Yoon, S.S. Synthesis and biological activity of novel substituted pyridines and purines containing 2,4-thiazolidinedione. Eur. J. Med. Chem., 2004, 39(5), 433-447.
[http://dx.doi.org/10.1016/j.ejmech.2004.03.001] [PMID: 15110969]
[36]
Ha, Y.M.; Park, Y.J.; Kim, J.A.; Park, D.; Park, J.Y.; Lee, H.J.; Lee, J.Y.; Moon, H.R.; Chung, H.Y. Design and synthesis of 5-(substituted benzylidene)thiazolidine-2,4-dione derivatives as novel tyrosinase inhibitors. Eur. J. Med. Chem., 2012, 49, 245-252.
[http://dx.doi.org/10.1016/j.ejmech.2012.01.019] [PMID: 22301213]
[37]
Chen, H.; Fan, Y.H.; Natarajan, A.; Guo, Y.; Iyasere, J.; Harbinski, F.; Luus, L.; Christ, W.; Aktas, H.; Halperin, J.A. Synthesis and biological evaluation of thiazolidine-2,4-dione and 2,4-thione derivatives as inhibitors of translation initiation. Bioorg. Med. Chem. Lett., 2004, 14(21), 5401-5405.
[http://dx.doi.org/10.1016/j.bmcl.2004.08.017] [PMID: 15454234]
[38]
Kim, S.H.; Choi, Y.J.; Moon, K.M.; Lee, H.J.; Woo, Y.; Chung, K.W.; Jung, Y.; Kim, S.; Chun, P.; Byun, Y.; Ha, Y.M.; Moon, H.R.; Chung, H.Y. The inhibitory effect of a synthetic compound, (Z)-5-(2,4-dihydroxybenzylidene) thiazolidine-2,4-dione (MHY498), on nitric oxide-induced melanogenesis. Bioorg. Med. Chem. Lett., 2013, 23(15), 4332-4335.
[http://dx.doi.org/10.1016/j.bmcl.2013.05.094] [PMID: 23806552]
[39]
Jeong, T.S.; Kim, J.R.; Kim, K.S.; Cho, K.H.; Bae, K.H.; Lee, W.S. Inhibitory effects of multi-substituted benzylidenethiazolidine-2,4-diones on LDL oxidation. Bioorg. Med. Chem., 2004, 12(15), 4017-4023.
[http://dx.doi.org/10.1016/j.bmc.2004.06.001] [PMID: 15246079]
[40]
Prakash, O.; Aneja, D.K.; Lohan, P.; Hussain, K.; Arora, S.; Sharma, C.; Aneja, K.R. Synthesis and antimicrobial activity of 5-((3-aryl-1-phenyl-1Hpyrazol-4-yl)methylene)thiazolidine-2,4-diones. Med. Chem. Res., 2012, 21, 2961-2968.
[http://dx.doi.org/10.1007/s00044-011-9829-4]
[41]
Mohammed Iqbal, A.K.; Khan, A.Y.; Kalashetti, M.B.; Belavagi, N.S.; Gong, Y.D.; Khazi, I.A.M. Synthesis, hypoglycemic and hypolipidemic activities of novel thiazolidinedione derivatives containing thiazole/triazole/oxadiazole ring. Eur. J. Med. Chem., 2012, 53, 308-315.
[http://dx.doi.org/10.1016/j.ejmech.2012.04.015] [PMID: 22575535]
[42]
Swathi, N.; Ramu, Y.; Subrahmanyam, C.V.S.; Satyanarayana, K. Synthesis, quantum mechanical calculation and biological evaluation of 5-(4-substituted aryl/hetero aryl methylidene)-1,3-thiazolidine-2,4-diones. Int. J. Pharm. Pharm. Sci., 2012, 4(2), 561-566.
[43]
Gupta, D.; Ghosh, N.N.; Chandra, R. Synthesis and pharmacological evaluation of substituted 5-[4-[2-(6,7-dimethyl-1,2,3,4-tetrahydro-2-oxo-4-quinoxalinyl)ethoxy]phenyl]methylene]thiazolidine-2,4-dione derivatives as potent euglycemic and hypolipidemic agents. Bioorg. Med. Chem. Lett., 2005, 15(4), 1019-1022.
[http://dx.doi.org/10.1016/j.bmcl.2004.12.041] [PMID: 15686904]
[44]
Jeon, R.; Kim, Y.J.; Cheon, Y.; Ryu, J.H. Synthesis and biological activity of [[(heterocycloamino)alkoxy] benzyl]-2,4-thiazolidinediones as PPARgamma agonists. Arch. Pharm. Res., 2006, 29(5), 394-399.
[http://dx.doi.org/10.1007/BF02968589] [PMID: 16756084]
[45]
Alagawadi, K.R.; Alegaon, S.G. Synthesis, characterization and antimicrobial activity evaluation of new 2,4-thiazolidinediones bearing imidazo[2,1-b][1,3,4]thiadiazole moiety. Arab. J. Chem., 2011, 4, 465-472.
[http://dx.doi.org/10.1016/j.arabjc.2010.07.012]
[46]
Alegaon, S.G.; Alagawadi, K.R. New thiazolidinedione-5-acetic acid amide derivatives: synthesis, characterization and investigation of antimicrobial and cytotoxic properties. Med. Chem. Res., 2012, 21, 816-824.
[http://dx.doi.org/10.1007/s00044-011-9598-0]
[47]
Avupati, V.R.; Yejella, R.P.; Akula, A.; Guntuku, G.S.; Doddi, B.R.; Vutla, V.R.; Anagani, S.R.; Adimulam, L.S.; Vyricharla, A.K. Synthesis, characterization and biological evaluation of some novel 2,4-thiazolidinediones as potential cytotoxic, antimicrobial and antihyperglycemic agents. Bioorg. Med. Chem. Lett., 2012, 22(20), 6442-6450.
[http://dx.doi.org/10.1016/j.bmcl.2012.08.052] [PMID: 22981328]
[48]
Jawale, D.V.; Pratap, U.R.; Rahuja, N.; Srivastava, A.K.; Mane, R.A. Synthesis and antihyperglycemic evaluation of new 2,4-thiazolidinediones having biodynamic aryl sulfonylurea moieties. Bioorg. Med. Chem. Lett., 2012, 22(1), 436-439.
[http://dx.doi.org/10.1016/j.bmcl.2011.10.110] [PMID: 22123321]
[49]
Kumar, A.; Chawla, A.; Jain, S.; Kumar, P.; Kumar, S. 3-Aryl-2-4-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxy]-phenyl-acrylic acid alkyl ester: synthesis and antihyperglycemic evaluation. Med. Chem. Res., 2011, 20, 678-686.
[http://dx.doi.org/10.1007/s00044-010-9369-3]
[50]
Yanagisawa, H.; Takamura, M.; Yamada, E.; Fujita, S.; Fujiwara, T.; Yachi, M.; Isobe, A.; Hagisawa, Y. Novel oximes having 5-benzyl-2,4-thiazolidinedione as antihyperglycemic agents: synthesis and structure-activity relationship. Bioorg. Med. Chem. Lett., 2000, 10(4), 373-375.
[http://dx.doi.org/10.1016/S0960-894X(00)00003-2] [PMID: 10714503]
[51]
Gim, H.J.; Kang, B.; Jeon, R. Synthesis and biological activity of 5-4-[2-(methyl-p-substitutedphenylamino)ethoxy]benzylthiazolidine-2,4-diones. Arch. Pharm. Res., 2007, 30(9), 1055-1061.
[http://dx.doi.org/10.1007/BF02980237] [PMID: 17958320]
[52]
Jeon, R.; Park, S. Synthesis and biological activity of benzoxazole containing thiazolidinedione derivatives. Arch. Pharm. Res., 2004, 27(11), 1099-1105.
[http://dx.doi.org/10.1007/BF02975111] [PMID: 15595409]
[53]
Nazreen, S.; Alam, M.S.; Hamid, H.; Yar, M.S.; Shafi, S.; Dhulap, A.; Alam, P.; Pasha, M.A.Q.; Bano, S.; Alam, M.M.; Haider, S.; Ali, Y.; Kharbanda, C.; Pillai, K.K. Design, synthesis, in silico molecular docking and biological evaluation of novel oxadiazole based thiazolidine-2,4-diones bis-heterocycles as PPAR-γ agonists. Eur. J. Med. Chem., 2014, 87, 175-185.
[http://dx.doi.org/10.1016/j.ejmech.2014.09.010] [PMID: 25255433]
[54]
Bhattarai, B.R.; Kafle, B.; Hwang, J.S.; Khadka, D.; Lee, S.M.; Kang, J.S.; Ham, S.W.; Han, I.O.; Park, H.; Cho, H. Thiazolidinedione derivatives as PTP1B inhibitors with antihyperglycemic and antiobesity effects. Bioorg. Med. Chem. Lett., 2009, 19(21), 6161-6165.
[http://dx.doi.org/10.1016/j.bmcl.2009.09.020] [PMID: 19783142]
[55]
Gouveia, F.L.; de Oliveira, R.M.; de Oliveira, T.B.; da Silva, I.M.; do Nascimento, S.C.; de Sena, K.X.; de Albuquerque, J.F. Synthesis, antimicrobial and cytotoxic activities of some 5-arylidene-4-thioxo-thiazolidine-2-ones. Eur. J. Med. Chem., 2009, 44(5), 2038-2043.
[http://dx.doi.org/10.1016/j.ejmech.2008.10.006] [PMID: 19027993]
[56]
Gaonkar, S.L.; Namratha, B.; Shetty, N.K.S.; Shimizu, H. Microwave- assisted synthesis and evaluation of N-substituted thiazolidine- 2,4-dione derivatives as antimicrobial agents. Interact. Med. Chem , 2014.
[http://dx.doi.org/10.7243/2053-7107-2-2]
[57]
Mohan, R.; Sharma, A.K.; Gupta, S.; Ramaa, C.S. Design, synthesis, and biological evaluation of novel 2,4-thiazolidinedione derivatives as histone deacetylase inhibitors targeting liver cancer cell line. Med. Chem. Res., 2012, 21, 1156-1165.
[http://dx.doi.org/10.1007/s00044-011-9623-3]
[58]
Kamal, A.; Srikanth, Y.V.V.; Khan, M.N.A.; Shaik, T.B.; Ashraf, M. Synthesis of 3,3-diindolyl oxyindoles efficiently catalysed by FeCl3 and their in vitro evaluation for anticancer activity. Bioorg. Med. Chem. Lett., 2010, 20(17), 5229-5231.
[http://dx.doi.org/10.1016/j.bmcl.2010.06.152] [PMID: 20673629]
[59]
Trotsko, N.; Przekora, A.; Zalewska, J.; Ginalska, G.; Paneth, A.; Wujec, M. Synthesis and in vitro antiproliferative and antibacterial activity of new thiazolidine-2,4-dione derivatives. J. Enzyme Inhib. Med. Chem., 2018, 33, 17-24.
[http://dx.doi.org/10.1080/14756366.2017.1387543] [PMID: 29098896]
[60]
Laxmi, S.V.; Anil, P.; Rajitha, G.; Rao, A.J.; Crooks, P.A.; Rajitha, B. Synthesis of thiazolidine-2,4-dione derivatives: Anticancer, antimicrobial and DNA cleavage studies. J. Chem. Biol., 2016, 9(4), 97-106.
[http://dx.doi.org/10.1007/s12154-016-0154-8] [PMID: 27698947]
[61]
Cho, H.; Tai, H.H. Thiazolidinediones as a novel class of NAD(+)-dependent 15-hydroxyprostaglandin dehydrogenase inhibitors. Arch. Biochem. Biophys., 2002, 405(2), 247-251.
[http://dx.doi.org/10.1016/S0003-9861(02)00352-1] [PMID: 12220539]
[62]
Liu, K.; Rao, W.; Parikh, H.; Li, Q.; Guo, T.L.; Grant, S.; Kellogg, G.E.; Zhang, S. 3,5-Disubstituted-thiazolidine-2,4-dione analogs as anticancer agents: Design, synthesis and biological characterization. Eur. J. Med. Chem., 2012, 47(1), 125-137.
[http://dx.doi.org/10.1016/j.ejmech.2011.10.031] [PMID: 22074985]
[63]
Azizmohammadi, M.; Khoobi, M.; Ramazani, A.; Emami, S.; Zarrin, A.; Firuzi, O.; Miri, R.; Shafiee, A. 2H-chromene derivatives bearing thiazolidine-2,4-dione, rhodanine or hydantoin moieties as potential anticancer agents. Eur. J. Med. Chem., 2013, 59, 15-22.
[http://dx.doi.org/10.1016/j.ejmech.2012.10.044] [PMID: 23202485]
[64]
Romagnoli, R.; Baraldi, P.G.; Salvador, M.K.; Camacho, M.E.; Balzarini, J.; Bermejo, J.; Estévez, F. Anticancer activity of novel hybrid molecules containing 5-benzylidene thiazolidine-2,4-dione. Eur. J. Med. Chem., 2013, 63, 544-557.
[http://dx.doi.org/10.1016/j.ejmech.2013.02.030] [PMID: 23537942]
[65]
Li, Q.; Al-Ayoubi, A.; Guo, T.; Zheng, H.; Sarkar, A.; Nguyen, T.; Eblen, S.T.; Grant, S.; Kellogg, G.E.; Zhang, S. Structure-activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione: Development of potential substrate-specific ERK1/2 inhibitors. Bioorg. Med. Chem. Lett., 2009, 19(21), 6042-6046.
[http://dx.doi.org/10.1016/j.bmcl.2009.09.057] [PMID: 19796943]
[66]
https://pubchem.ncbi.nlm.nih.gov/compound/9832447
[67]
Joshi, H.; Pal, T.; Ramaa, C.S. A new dawn for the use of thiazolidinediones in cancer therapy. Expert Opin. Investig. Drugs, 2014, 23(4), 501-510.
[http://dx.doi.org/10.1517/13543784.2014.884708] [PMID: 24597633]
[68]
https://clinicaltrials.gov/ct2/show/record/NCT02249949
[69]
Yakubu-Madus, F.E.; Stramm, L.E.; Vignati, L.; Johnson, W.T. Method for treating non-insulin dependent diabetes using thiazolidinediones with glucagonlike peptide-1 and agonists thereof. US Pat., 11/650., 410. 2009.
[70]
Meguro, K.; Fujita, T. Thiazolidinedione derivatives, useful as antidiabetic agents. US Pat., 820,390. 1987.
[71]
Meguro, K.; Fujita, T.; Hatanaka, C.; Ooi, S. A method for producing thiazolidinedione derivatives. Europ. Pat., 87306425.7 , 1991.
[72]
Antonucci, T.; Lockwood, D.; Norris, R. Use of thiazolidinedione derivatives in the treatment of anovulation, hyperandrogenism and hirsutism. US Pat., 09/124 , 1999.
[73]
Hitoshi, I.; Takashi, S.; Hiroyuki, O. Pharmaceutical composition comprising pioglitazone and glimepiride for use in treatment of diabetes. 01203170.4 , 2009.
[74]
Hefny, ALS Potentiometric device and method selective for Pioglitazone. World Intellect. Property Organ , PCT/US2014/044041. 2015.
[75]
Bente, R.; Henriksen, K.; Kumar, R. Balaglitazone compositions and methods. US Pat., 13/516,917 , 2013.
[76]
Kalayoglu, M.V.; Singer, M.S. Methods and compositions for locally increasing body fat. US Pat., 14/086,785 . 2014.

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