An overview on medicinal perspective of thiazolidine-2,4-dione: A remarkable scaffold in the treatment of type 2 diabetes

被引:75
作者
Bansal, Garima [1 ]
Thanikachalam, Punniyakoti Veeraveedu [1 ,2 ]
Maurya, Rahul K. [1 ,3 ]
Chawla, Pooja [1 ]
Ramamurthy, Srinivasan [4 ]
机构
[1] ISF Coll Pharm, Dept Pharmaceut Chem, Moga 142001, Punjab, India
[2] GRT Inst Pharmaceut Educ & Res, Grt Mahalakshmi Nagar, Tiruttani, India
[3] Amity Univ Uttar Pradesh, Amity Inst Pharm, Lucknow Campus, Lucknow, Uttar Pradesh, India
[4] Univ Sci & Technol Fujairah, Coll Pharm & Hlth Sci, Fujairah, U Arab Emirates
关键词
Diabetes; PPAR-gamma; Thiazolidine-2,4-diones; Pioglitazone; Rosiglitazone; PPAR-GAMMA AGONISTS; VIVO ANTIDIABETIC ACTIVITY; INCRETIN-BASED DRUGS; BIOLOGICAL-ACTIVITY; THIAZOLIDINEDIONE DERIVATIVES; HYPOLIPIDEMIC AGENTS; MOLECULAR DOCKING; IN-VITRO; PEROXISOME PROLIFERATOR; JAPANESE PATIENTS;
D O I
10.1016/j.jare.2020.01.008
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Diabetes or diabetes mellitus is a complex or polygenic disorder, which is characterized by increased levels of glucose (hyperglycemia) and deficiency in insulin secretion or resistance to insulin over an elongated period in the liver and peripheral tissues. Thiazolidine-2,4-dione (TZD) is a privileged scaffold and an outstanding heterocyclic moiety in the field of drug discovery, which provides various opportunities in exploring this moiety as an antidiabetic agent. In the past few years, various novel synthetic approaches had been undertaken to synthesize different derivatives to explore them as more potent antidiabetic agents with devoid of side effects (i.e., edema, weight gain, and bladder cancer) of clinically used TZD (pioglitazone and rosiglitazone). In this review, an effort has been made to summarize the up to date research work of various synthetic strategies for TZD derivatives as well as their biological significance and clinical studies of TZDs in combination with other category as antidiabetic agents. This review also highlights the structure-activity relationships and the molecular docking studies to convey the interaction of various synthesized novel derivatives with its receptor site. (C) 2020 The Authors. Published by Elsevier B.V. on behalf of Cairo University.
引用
收藏
页码:163 / 205
页数:43
相关论文
共 102 条
[91]   Synthesis, Characterization, Biological Evaluation and Docking of Coumarin Coupled Thiazolidinedione Derivatives and its Bioisosteres as PPAR Agonists [J].
Shukla, Shubhanjali ;
Kumar, Pankaj ;
Das, Nirupam ;
Moorthy, N. S. Hari Narayana ;
Shrivastava, Sushant Kumar ;
Trivedi, Piyush ;
Srivastava, Radhey Shyam .
MEDICINAL CHEMISTRY, 2012, 8 (05) :834-845
[92]   Thiazolidinediones and the Promise of Insulin Sensitization in Type 2 Diabetes [J].
Soccio, Raymond E. ;
Chen, Eric R. ;
Lazar, Mitchell A. .
CELL METABOLISM, 2014, 20 (04) :573-591
[93]   STUDIES ON ANTIDIABETIC AGENTS .11. NOVEL THIAZOLIDINEDIONE DERIVATIVES AS POTENT HYPOGLYCEMIC AND HYPOLIPIDEMIC AGENTS [J].
SOHDA, T ;
MIZUNO, K ;
MOMOSE, Y ;
IKEDA, H ;
FUJITA, T ;
MEGURO, K .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (14) :2617-2626
[94]   Vanadyl-thiazolidinedione combination agents for diabetes therapy [J].
Storr, T ;
Mitchell, D ;
Buglyó, P ;
Thompson, KH ;
Yuen, VG ;
McNeill, JH ;
Orvig, C .
BIOCONJUGATE CHEMISTRY, 2003, 14 (01) :212-221
[95]   Synthesis and biological activity of metabolites of the antidiabetic, antihyperglycemic agent pioglitazone [J].
Tanis, SP ;
Parker, TT ;
Colca, JR ;
Fisher, RM ;
Kletzein, RF .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (26) :5053-5063
[96]   Rhodanine as a Privileged Scaffold in Drug Discovery [J].
Tomasic, T. ;
Masic, L. P. .
CURRENT MEDICINAL CHEMISTRY, 2009, 16 (13) :1596-1629
[97]   Pioglitazone improves glucose metabolism and modulates skeletal muscle TIMP-3-TACE dyad in type 2 diabetes mellitus: a randomised, double-blind, placebo-controlled, mechanistic study [J].
Tripathy, Devjit ;
Daniele, Giuseppe ;
Fiorentino, Teresa V. ;
Perez-Cadena, Zandra ;
Chavez-Velasquez, Alberto ;
Kamath, Subhash ;
Fanti, Paolo ;
Jenkinson, Christopher ;
Andreozzi, Francesco ;
Federici, Massimo ;
Gastaldelli, Amalia ;
DeFronzo, Ralph A. ;
Folli, Franco .
DIABETOLOGIA, 2013, 56 (10) :2153-2163
[98]  
Tuncbilek Meral, 2003, Farmaco (Lausanne), V58, P79, DOI 10.1016/S0014-827X(02)01241-7
[99]   Synthesis and antidiabetic activity of 2,4-thiazolidindione, imidazolidinedione and 2-thioxo-imidazolidine-4-one derivatives bearing 6-methyl chromonyl pharmacophore [J].
Unlusoy, Meltem Ceylan ;
Kazak, Canan ;
Bayro, Ornela ;
Verspohl, Eugen J. ;
Ertan, Rahmiye ;
Dundar, Oya Bozdag .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2013, 28 (06) :1205-1210
[100]   Effects on the incidence of cardiovascular events of the addition of pioglitazone versus sulfonylureas in patients with type 2 diabetes inadequately controlled with metformin (TOSCA. IT): a randomised, multicentre trial [J].
Vaccaro, Olga ;
Masulli, Maria ;
Nicolucci, Antonio ;
Bonora, Enzo ;
Del Prato, Stefano ;
Maggioni, Aldo P. ;
Rivellse, Angela A. ;
Squatrito, Sebastian ;
Giorda, Carlo B. ;
Sesti, Giorgio ;
Mocarelli, Paolo ;
Lucisaiio, Giuseppe ;
Sacco, Micheie ;
Signorini, Stefano ;
Cappellini, Fabrizio ;
Perriello, Gabriefe ;
Babini, Anna Carla ;
Lapolla, Annunziata ;
Gregori, Giovonna ;
Giordano, Carla ;
Corsi, Laura ;
Buzzetti, Raffaeffa ;
Clemente, Gennaro ;
Di Cianni, Graziano ;
Iannarelli, Rossella ;
Cordera, Renzo ;
La Macchia, Olga ;
Zamboni, Chiara ;
Scaranna, Cristiana ;
Boemi, Massimo ;
Iovine, Ciro ;
Lauro, Davide ;
Leotta, Sergio ;
Dall'Aglio, Elisabetta ;
Cannarsa, Emanuela ;
Tonutti, Laura ;
Pugliese, Giuseppe ;
Bossi, Antonio C. ;
Anichini, Roberto ;
Dotta, Francesco ;
Di Benedetto, Antonin ;
Citro, Giuseppe ;
Antenucci, Daniela ;
Ricci, Lucia ;
Giorgino, Francesco ;
Santini, Costanza ;
Gnasso, Agostino ;
De Cosmo, Salvatore ;
Zavaroni, Donatella ;
Vedovato, Monica .
LANCET DIABETES & ENDOCRINOLOGY, 2017, 5 (11) :887-897