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Mini-Reviews in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

Mini-Review Article

A Review on the Synthesis and Biological Studies of 2,4-Thiazolidinedione Derivatives

Author(s): Srinivasa Reddy Bireddy*, Veera Swamy Konkala, Chandraiah Godugu and Pramod Kumar Dubey

Volume 17, Issue 8, 2020

Page: [958 - 974] Pages: 17

DOI: 10.2174/1570193X17666200221123633

Price: $65

Abstract

2,4-Thiazolidinediones are versatile scaffolds with a unique structural feature of hydrogen bonding donor and the hydrogen bonding acceptor region. This review deals with the synthesis of various bio-active 2,4-thiazolidinedione derivatives. It is presented on the basis of the linker variations at 3rd & 5th positions of 2,4-thizolidinediones. Biological evaluations of various derivatives thus prepared and toxicity studies on the respective products as given by various researchers/ Research groups have been described.

Keywords: 2, 4-Thiazolidinediones, antidiabetic activity, glitazones, Knoevenagel condensation, acid hydrolysis, type-2 diabetes.

Graphical Abstract
[1]
Elzahhar, P.A.; Alaaeddine, R.; Ibrahim, T.M.; Nassra, R.; Ismail, A.; Chua, B.S.K.; Frkic, R.L.; Bruning, J.B.; Wallner, N.; Knape, T.; von Knethen, A.; Labib, H.; El-Yazbi, A.F.; Belal, A.S.F. Shooting three inflammatory targets with a single bullet: Novel multi-targeting anti-inflammatory glitazones. Eur. J. Med. Chem., 2019, 167, 562-582.
[http://dx.doi.org/10.1016/j.ejmech.2019.02.034] [PMID: 30818268]
[2]
Levshin, I.B.; Rastorgueva, N.A.; Kiselev, A.V.; Vedenkin, A.S.; Stovbun, S.V.; Churakov, A.V.; Saveliev, O.Y.; Polshakov, V.I. Thiazolidine-2,4-dione in benzoylation reaction. Chem. Heterocycl. Compd., 2019, 55, 178-183.
[http://dx.doi.org/10.1007/s10593-019-02436-2]
[3]
Hussain, F.; Khan, Z.; Jan, M.S.; Ahmad, S.; Ahmad, A.; Rashid, U.; Ullah, F.; Ayaz, M.; Sadiq, A. Synthesis, in vitro α-glucosidase inhibition, antioxidant, in vivo antidiabetic and molecular docking studies of pyrrolidine-2,5-dione and thiazolidine-2,4-dione derivatives. Bioorg. Chem., 2019. 91103128
[http://dx.doi.org/10.1016/j.bioorg.2019.103128] [PMID: 31369977]
[4]
Sun, J.; He, W.; Liu, H.Y.; Qin, J.; Ye, C.L. Design, synthesis and molecular docking of 1,4-benzodioxane thiazolidinedione piperazine derivatives as FabH inhibitors. Bioorg. Chem., 2019, 88102958
[http://dx.doi.org/10.1016/j.bioorg.2019.102958] [PMID: 31054434]
[5]
Marc, G.; Stana, A.; Oniga, S.D.; Pîrnău, A.; Vlase, L.; Oniga, O. New Phenolic derivatives of thiazolidine-2,4-dione with antioxidant and antiradical properties: Synthesis, characterization, in vitro evaluation, and quantum studies. Molecules, 2019, 24(11), 2060.
[http://dx.doi.org/10.3390/molecules24112060] [PMID: 31151176]
[6]
Whiting, E.; Raje, M.R.; Chauhan, J.; Wilder, P.T.; Van Eker, D.; Hughes, S.J.; Bowen, N.G.; Vickers, G.E.A.; Fenimore, I.C.; Fletcher, S. Discovery of Mcl-1 inhibitors based on a thiazolidine-2,4-dione scaffold. Bioorg. Med. Chem. Lett., 2018, 28(3), 523-528.
[http://dx.doi.org/10.1016/j.bmcl.2017.11.023] [PMID: 29329659]
[7]
Satish, S.; Srivastava, A.; Yadav, P.; Varshney, S.; Choudhary, R.; Balaramnavar, V.M.; Narender, T.; Gaikwad, A.N. Aegeline inspired synthesis of novel amino alcohol and thiazolidinedione hybrids with antiadipogenic activity in 3T3-L1 cells. Eur. J. Med. Chem., 2018, 143, 780-791.
[http://dx.doi.org/10.1016/j.ejmech.2017.11.041] [PMID: 29220798]
[8]
Reddy, M.U.; Reddy, M.C.S. Synthesis and antidiabetic evaluation of 5-(2-methoxy-6-pentadecylbenzylidene)-3-alkyl/aryl substituted thiazolidine-2,4-dione derivatives. Asian J. Chem., 2018, 30, 1231-1236.
[http://dx.doi.org/10.14233/ajchem.2018.21168]
[9]
Mahapatra, M.K.; Kumar, R.; Kumar, M. Exploring sulfonate esters of 5-arylidene thiazolidine-2,4-diones as PTP1B inhibitors with anti-hyperglycemic activity. Med. Chem. Res., 2017, 27, 476-487.
[http://dx.doi.org/10.1007/s00044-017-2074-8]
[10]
Tran, H.Q.; Nguyen, H.C.; Van Nguyen, T.; Nguyen, T.T.; Vo, T.N.; Nguyend, C.T. Synthesis and evaluation of cytotoxic activity on MCF-7 cell line of some diesters derived from 5-(hydroxy-benzylidene)thiazolidine-2,4-diones. Acta Chem. Iasi, 2018, 26, 233-248.
[http://dx.doi.org/10.2478/achi-2018-0015]
[11]
Sucheta, S.T.; Verma, P.K. Synthesis, SAR and in vitro therapeutic potentials of thiazolidine-2,4-diones. Chem. Cent. J., 2018, 12(1), 129-140.
[http://dx.doi.org/10.1186/s13065-018-0496-0] [PMID: 30515635]
[12]
Lohray, B.B.; Bhushan, V.; Rao, B.P.; Madhavan, G.R.; Murali, N.; Rao, K.N.; Reddy, A.K.; Rajesh, B.M.; Reddy, P.G.; Chakrabarti, R.; Vikramadithyan, R.K.; Rajagopalan, R.; Mamidi, R.N.V.S.; Jajoo, H.K.; Subramaniam, S. Novel euglycemic and hypolipidemic agents. J. Med. Chem., 1998, 41(10), 1619-1630.
[http://dx.doi.org/10.1021/jm970444e] [PMID: 9572887]
[13]
Prabhakar, C.; Madhusudhan, G.; Sahadev, K.; Reddy, C.M.; Sarma, M.R.; Reddy, G.O.; Chakrabarti, R.; Rao, C.S.; Kumar, T.D.; Rajagopalan, R. Synthesis and biological activity of novel thiazolidinediones. Bioorg. Med. Chem. Lett., 1998, 8(19), 2725-2730.
[http://dx.doi.org/10.1016/S0960-894X(98)00485-5] [PMID: 9873611]
[14]
Sunduru, N.; Srivastava, K.; Rajakumar, S.; Puri, S.K.; Saxena, J.K.; Chauhan, P.M. 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]
[15]
Reddy, K.A.; Lohray, B.B.; Bhushan, V.; Reddy, A.S.; Kishore, P.H.; Rao, V.V.; Saibaba, V.; Bajji, A.C.; Rajesh, B.M.; Reddy, K.V.; Chakrabarti, R.; Rajagopalan, R. Novel euglycemic and hypolipidemic agents: Part-2. Antioxidant moiety as structural motif. Bioorg. Med. Chem. Lett., 1998, 8(9), 999-1002.
[http://dx.doi.org/10.1016/S0960-894X(98)00159-0] [PMID: 9871696]
[16]
Hafez, H.N.; El-Gazzar, A.R. Synthesis and antitumor activity of substituted triazolo[4,3-a]pyrimidin-6-sulfonamide with an incorporated thiazolidinone moiety. Bioorg. Med. Chem. Lett., 2009, 19(15), 4143-4147.
[http://dx.doi.org/10.1016/j.bmcl.2009.05.126] [PMID: 19540114]
[17]
Bonde, C.G.; Gaikwad, N.J. Synthesis and preliminary evaluation of some pyrazine containing thiazolines and thiazolidinones as antimicrobial agents. Bioorg. Med. Chem., 2004, 12(9), 2151-2161.
[http://dx.doi.org/10.1016/j.bmc.2004.02.024] [PMID: 15080915]
[18]
Fan, Y-H.; Chen, H.; Natarajan, A.; Guo, Y.; Harbinski, F.; Iyasere, J.; Christ, W.; Aktas, H.; Halperin, J.A. Structure-activity requirements for the antiproliferative effect of troglitazone derivatives mediated by depletion of intracellular calcium. Bioorg. Med. Chem. Lett., 2004, 14(10), 2547-2550.
[http://dx.doi.org/10.1016/j.bmcl.2004.02.087] [PMID: 15109648]
[19]
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]
[20]
Madhavan, G.R.; Chakrabarti, R.; Reddy, K.A.; Rajesh, B.M.; Balraju, V.; Rao, P.B.; Rajagopalan, R.; Iqbal, J. Dual PPAR-α and,
γ activators derived from novel benzoxazinone containing thiazolidinediones having antidiabetic and hypolipidemic potential. Bioorg. Med. Chem., 2006, 14(2), 584-591.
[http://dx.doi.org/10.1016/j.bmc.2005.08.043] [PMID: 16198573]
[21]
Hossain, S.U.; Bhattacharya, S. Synthesis of O-prenylated and O-geranylated derivatives of 5-benzylidene2,4-thiazolidinediones and evaluation of their free radical scavenging activity as well as effect on some phase II antioxidant/detoxifying enzymes. Bioorg. Med. Chem. Lett., 2007, 17(5), 1149-1154.
[http://dx.doi.org/10.1016/j.bmcl.2006.12.040] [PMID: 17197183]
[22]
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]
[23]
Sambasivarao, S.V.; Soni, L.K.; Gupta, A.K.; Hanumantharao, P.; Kaskhedikar, S.G. Quantitative structure-activity analysis of 5-arylidene-2,4-thiazolidinediones as aldose reductase inhibitors. Bioorg. Med. Chem. Lett., 2006, 16(3), 512-520.
[http://dx.doi.org/10.1016/j.bmcl.2005.10.069] [PMID: 16297625]
[24]
Heng, S.; Tieu, W.; Hautmann, S.; Kuan, K.; Pedersen, D.S.; Pietsch, M.; Gütschow, M.; Abell, A.D. New cholesterol esterase inhibitors based on rhodanine and thiazolidinedione scaffolds. Bioorg. Med. Chem., 2011, 19(24), 7453-7463.
[http://dx.doi.org/10.1016/j.bmc.2011.10.042] [PMID: 22075233]
[25]
Wu, Y.; Tai, H-H.; Cho, H. Synthesis and SAR of thiazolidinedione derivatives as 15-PGDH inhibitors. Bioorg. Med. Chem., 2010, 18(4), 1428-1433.
[http://dx.doi.org/10.1016/j.bmc.2010.01.016] [PMID: 20122835]
[26]
Hu, B.; Ellingboe, J.; Gunawan, I.; Han, S.; Largis, E.; Li, Z.; Malamas, M.; Mulvey, R.; Oliphant, A.; Sum, F-W.; Tillett, J.; Wong, V. 2,4-Thiazolidinediones as potent and selective human β3 agonists. Bioorg. Med. Chem. Lett., 2001, 11(6), 757-760.
[http://dx.doi.org/10.1016/S0960-894X(01)00063-4] [PMID: 11277513]
[27]
Koide, Y.; Tatsui, A.; Hasegawa, T.; Murakami, A.; Satoh, S.; Yamada, H.; Kazayama, S.; Takahashi, A. Identification of a stable chymase inhibitor using a pharmacophore-based database search. Bioorg. Med. Chem. Lett., 2003, 13(1), 25-29.
[http://dx.doi.org/10.1016/S0960-894X(02)00853-3] [PMID: 12467610]
[28]
Brooke, E.W.; Davies, S.G.; Mulvaney, A.W.; Okada, M.; Pompeo, F.; Sim, E.; Vickers, R.J.; Westwood, I.M. Synthesis and in vitro evaluation of novel small molecule inhibitors of bacterial arylamine N-acetyltransferases (NATs). Bioorg. Med. Chem. Lett., 2003, 13(15), 2527-2530.
[http://dx.doi.org/10.1016/S0960-894X(03)00484-0] [PMID: 12852958]
[29]
Alcaraz, L.; Baxter, A.; Bent, J.; Bowers, K.; Braddock, M.; Cladingboel, D.; Donald, D.; Fagura, M.; Furber, M.; Laurent, C.; Lawson, M.; Mortimore, M.; McCormick, M.; Roberts, N.; Robertson, M. Novel P2X7 receptor antagonists. Bioorg. Med. Chem. Lett., 2003, 13(22), 4043-4046.
[http://dx.doi.org/10.1016/j.bmcl.2003.08.033] [PMID: 14592504]
[30]
Komatsu, T.; Hirano, T.; Songkram, C.; Kawachi, E.; Kagechika, H. Novel thyroid hormone receptor antagonists with an N-alkylated diphenylamine skeleton. Bioorg. Med. Chem., 2007, 15(9), 3115-3126.
[http://dx.doi.org/10.1016/j.bmc.2007.02.053] [PMID: 17363258]
[31]
Bhattarai, B.R.; Kafle, B.; Hwang, J-S.; Ham, S.W.; Lee, K-H.; Park, H.; Han, I-O.; Cho, H. Novel thiazolidinedione derivatives with anti-obesity effects: Dual action as PTP1B inhibitors and PPAR-γ activators. Bioorg. Med. Chem. Lett., 2010, 20(22), 6758-6763.
[http://dx.doi.org/10.1016/j.bmcl.2010.08.130] [PMID: 20850970]
[32]
Ottanà, R.; Maccari, R.; Ciurleo, R.; Paoli, P.; Jacomelli, M.; Manao, G.; Camici, G.; Laggner, C.; Langer, T. 5-Arylidene-2-phenylimino-4-thiazolidinones as PTP1B and LMW-PTP inhibitors. Bioorg. Med. Chem., 2009, 17(5), 1928-1937.
[http://dx.doi.org/10.1016/j.bmc.2009.01.044] [PMID: 19217304]
[33]
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]
[34]
Li, Q.; Wu, J.; Zheng, H.; Liu, K.; Guo, T.L.; Liu, Y.; Eblen, S.T.; Grant, S.; Zhang, S. Discovery of 3-(2-aminoethyl)-5-(3-phenyl-propylidene)-thiazolidine-2,4-dione as a dual inhibitor of the Raf/MEK/ERK and the PI3K/Akt signaling pathways. Bioorg. Med. Chem. Lett., 2010, 20(15), 4526-4530.
[http://dx.doi.org/10.1016/j.bmcl.2010.06.030] [PMID: 20580230]
[35]
Shoda, T.M.E.; Imamia, Y.; Sugiyama, T.; Kawamatsu, Y. studies on antidiabeti agents and its derivatives. Chem. Pharm. Bull. (Tokyo), 1982, 30, 3580-3600.
[36]
Aizawa, Y.; Kanai, T.; Fujita, T.; Horikoshi, H.; Yoshioka, T. Studies on Hindered phenols and analogues. Part 4. Formation of 3, 9‐dioxabicyclo (4.3.1) decanes and their application for antidiabetic agents. ChemInform, 1991, 22, 32-40.
[37]
Yoshioka, T.; Fujita, T.; Kanai, T.; Aizawa, Y.; Kurumada, T.; Hasegawa, K.; Horikoshi, H. Studies on hindered phenols and analogues. 1. Hypolipidemic and hypoglycemic agents with ability to inhibit lipid peroxidation. J. Med. Chem., 1989, 32(2), 421-428.
[http://dx.doi.org/10.1021/jm00122a022] [PMID: 2913302]
[38]
Urban, F.J.; Moore, B.S. Synthesis of optically active 2‐benzyldihydrobenzopyrans for the hypoglycemic agent englitazone. J. Heterocycl. Chem., 1992, 29, 431-438.
[http://dx.doi.org/10.1002/jhet.5570290223]
[39]
Momose, Y.M.K.; Hitoshi, I.; Satoru, O.; Sodha, T. Studies on antidiabetic agnets of pioglitazone. Chem. Pharm. Bull. (Tokyo), 1991, 36, 1440-1445.
[http://dx.doi.org/10.1248/cpb.39.1440] [PMID: 1934164]
[40]
Cantello, B.C.; Cawthorne, M.A.; Haigh, D.; Hindley, R.M.; Smith, S.A.; Thurlby, P.L. The synthesis of BRL 49653-a novel and potent antihyperglycaemic agent. Bioorg. Med. Chem. Lett., 1994, 4, 1181-1184.
[http://dx.doi.org/10.1016/S0960-894X(01)80325-5]
[41]
Santosh, L.G. Shimizu, H. Microwave synthesis. Tetrahedron, 2010, 66, 3314-3317.
[42]
Kumar, B.R.; Nanjan, M.J. Novel glitazones: Design, synthesis, glucose uptake and structure-activity relationships. Bioorg. Med. Chem. Lett., 2010, 20(6), 1953-1956.
[http://dx.doi.org/10.1016/j.bmcl.2010.01.125] [PMID: 20167487]
[43]
Drawanz, B.B.; Ribeiro, C.S.; Masteloto, H.G.; Neuenfeldt, P.D.; Pereira, C.M.; Siqueira, G.M.; Cunico, W. Sonochemistry: A good, fast and clean method to promote the synthesis of 5-arylidene-2,4-thiazolidinediones. Ultrason. Sonochem., 2014, 21(5), 1615-1617.
[http://dx.doi.org/10.1016/j.ultsonch.2014.04.013] [PMID: 24830818]
[44]
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]
[45]
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]
[46]
Kallanagouda, R.A.; Shankar, G.A. 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]
[47]
Khaled, M.D.; Ismail, S.; Mostafa, S.M.S.G.M.; Helal, M.A. Benzimidazole containing thiazolidinediones. Eur. J. Med. Chem., 2016, 109, 57.
[48]
Liu, X.F.C-J. Synthesis of new chalcone derivatives bearing 2,4-thiazolidinedione and benzoic acid moieties. Eur. J. Med. Chem., 2011, 46, 3469-3473.
[49]
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]
[50]
Kamel, M.; Harris, P.; Dimitris, K. synthesized two series of novel 2,4-thiazolidinedione derivatives. Eur. J. Med. Chem., 2017, 133, 340-346.
[51]
Mohanty, S.; Roy, A.K.; Reddy, G.S.; Kumar, K.V. RamaDevi, B.; Bhargavi, G.; Karmakar, A.C., Knoevenagel condensation of aromatic bisulfite adducts with 2, 4-thiazolidinedione in the presence of Lewis acid catalysts. Tetrahedron Lett., 2015, 56, 2564-2567.
[http://dx.doi.org/10.1016/j.tetlet.2015.03.117]
[52]
Mohanty, S.R.A.K.; Reddy, G.S.; Vinay, K.P. RamaDevi, B.; Bhargavi, G.; Arun, C.K., Knoevenagel condensation of 2,4-thiazolidinedione. Tetrahedron Lett., 2014, 56, 4585-4590.
[http://dx.doi.org/10.1016/j.tetlet.2014.06.082]
[53]
Sharma, R.K.; Younis, Y.; Mugumbate, G.; Njoroge, M.; Gut, J.; Rosenthal, P.J.; Chibale, K. Synthesis and structure-activity-relationship studies of thiazolidinediones as antiplasmodial inhibitors of the Plasmodium falciparum cysteine protease falcipain-2. Eur. J. Med. Chem., 2015, 90, 507-518.
[http://dx.doi.org/10.1016/j.ejmech.2014.11.061] [PMID: 25486422]
[54]
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-1H-pyrazol-4-yl) methylene) thiazolidine-2, 4-diones. Med. Chem. Res., 2012, 21, 2961-2968.
[http://dx.doi.org/10.1007/s00044-011-9829-4]
[55]
Nazreen, S.; Alam, M.S.; Hamid, H.; Yar, M.S.; Shafi, S.; Dhulap, A.; Alam, P.; Pasha, M.A.; 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]
[56]
Nazreen, S.; Alam, M.S.; Hamid, H.; Yar, M.S.; Dhulap, A.; Alam, P.; Pasha, M.A.; Bano, S.; Alam, M.M.; Haider, S.; Kharbanda, C.; Ali, Y.; Pillai, K.K. Thiazolidine-2,4-diones derivatives as PPAR-γ agonists: Synthesis, molecular docking, in vitro and in vivo antidiabetic activity with hepatotoxicity risk evaluation and effect on PPAR-γ gene expression. Bioorg. Med. Chem. Lett., 2014, 24(14), 3034-3042.
[http://dx.doi.org/10.1016/j.bmcl.2014.05.034] [PMID: 24890090]
[57]
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]
[58]
Madhavan, G.R.; Chakrabarti, R.; Kumar, S.K.; Misra, P.; Mamidi, R.N.; Balraju, V.; Kasiram, K.; Babu, R.K.; Suresh, J.; Lohray, B.B.; Lohrayb, V.B.; Iqbal, J.; Rajagopalan, R. Novel phthalazinone and benzoxazinone containing thiazolidinediones as antidiabetic and hypolipidemic agents. Eur. J. Med. Chem., 2001, 36(7-8), 627-637.
[http://dx.doi.org/10.1016/S0223-5234(01)01257-0] [PMID: 11600232]
[59]
Bhanushali, U.; Rajendran, S.; Sarma, K.; Kulkarni, P.; Chatti, K.; Chatterjee, S.; Ramaa, C.S. 5-Benzylidene-2,4-thiazolidenedione derivatives: Design, synthesis and evaluation as inhibitors of angiogenesis targeting VEGR-2. Bioorg. Chem., 2016, 67, 139-147.
[http://dx.doi.org/10.1016/j.bioorg.2016.06.006] [PMID: 27388635]
[60]
Aneja, D.K.; Lohan, P.; Arora, S.; Sharma, C.; Aneja, K.R.; Prakash, O. Synthesis of new pyrazolyl-2, 4-thiazolidinediones as antibacterial and antifungal agents. Org. Med. Chem. Lett., 2011, 1(1), 15.
[http://dx.doi.org/10.1186/2191-2858-1-15] [PMID: 22373217]
[61]
Suresh, S.J.S. Ultrasound-assisted synthesis of 2,4-thiazoli-dinedione derivatives. Org. Med. Chem. Lett., 2013, 3(1), 2.
[62]
Shelke, K.F.; Sapkal, S.B.; Kakade, G.K.; Sadaphal, S.A.; Shingate, B.B.; Shingare, M.S. Alum catalyzed simple and efficient synthesis of 5-arylidene-2, 4-thiazolidinedione in aqueous media. Green Chem. Lett. Rev., 2010, 3, 17-21.
[http://dx.doi.org/10.1080/17518250903478345]
[63]
Jawale, D.V.; Pratap, U.R.; Lingampalle, D.L.; Mane, R.A. Dicationic ionic liquid mediated synthesis of 5‐arylidine‐2, 4‐thia-zolidinediones. Chin. J. Chem., 2011, 29, 942-946.
[http://dx.doi.org/10.1002/cjoc.201190192]
[64]
Neogi, P.; Lakner, F.J.; Medicherla, S.; Cheng, J.; Dey, D.; Gowri, M.; Nag, B.; Sharma, S.D.; Pickford, L.B.; Gross, C. Synthesis and structure-activity relationship studies of cinnamic acid-based novel thiazolidinedione antihyperglycemic agents. Bioorg. Med. Chem., 2003, 11(18), 4059-4067.
[http://dx.doi.org/10.1016/S0968-0896(03)00393-6] [PMID: 12927868]
[65]
Riyaz, S.N.A.; Dubey, P.K. PEG-600 mediated one-pot synthesis of quinolinylidinethiazolidine-2,4- diones as potential anti-hyperglycemic agents. Indian J. Chem., 2012, 51B, 1396.
[66]
Konkala, V.S.; Dubey, P.K. Urea/thiourea: Efficient, inexpensive and reusable catalysts for the synthesis of pyrazole derivatives with 2-iminothiazolidin-4-one and 2,4-thiazolidinediones under solventfree conditions. Mol. Divers., 2017, 21(2), 283, 291.
[http://dx.doi.org/10.1007/s11030-016-9719-2] [PMID: 28054284]

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