Literature DB >> 32154036

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

Garima Bansal1, Punniyakoti Veeraveedu Thanikachalam1,2, Rahul K Maurya1,3, Pooja Chawla1, Srinivasan Ramamurthy4.   

Abstract

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.
© 2020 THE AUTHORS. Published by Elsevier BV on behalf of Cairo University.

Entities:  

Keywords:  ADDP, 1,1′-(Azodicarbonyl)dipiperidine; AF, activation factor; ALP, alkaline phosphatase; ALT, alanine transaminase; AST, aspartate transaminase; Boc, Butyloxycarbonyl; DBD, DNA-binding domain; DCM, dichloromethane; DM, diabetes mellitus; DMF, dimethylformamide; DMSO, dimethyl sulfoxide; DNA, deoxyribonucleic acid; Diabetes; E, Entgegen; ECG, electrocardiogram; FDA, food and drug administration; FFA, free fatty acid; GAL4, Galactose transporter type; GLUT4, glucose transporter type 4; GPT, glutamic pyruvic transaminase; HCl, Hydrochloric Acid; HDL, high-density lipoprotein; HEK, human embryonic kidney; HEp-2, Human epithelial type 2; HFD, high-fat diet; IDF, international diabetes federation; IL-β, interlukin-beta; INS-1, insulin-secreting cells; K2CO3, Potassium carbonate; KOH, potassium hydroxide; LBD, ligand-binding domain; LDL, low-density lipoprotein; MDA, malondialdehyde; NA, nicotinamide; NBS, N-bromosuccinimide; NFκB, nuclear factor kappa-B; NO, nitric oxide; NaH, Sodium Hydride; OGTT, oral glucose tolerance test; PDB, protein data bank; PPAR, peroxisome-proliferator activated receptor; PPAR-γ; PPRE, peroxisome proliferator response element; PTP1B, protein-tyrosine phosphatase 1B; Pd, Palladium; Pioglitazone; QSAR, quantitative structure-activity relationship; RXR, retinoid X receptor; Rosiglitazone; SAR, structure-activity relationship; STZ, streptozotocin; T2DM, type 2 diabetes mellitus; TFA, trifluoroacetic acid; TFAA, trifluoroacetic anhydride; TG, triglycerides; THF, tetrahydrofuran; TNF-α, tumor necrosis factor-alpha; TZD, thiazolidine-2,4-dione; Thiazolidine-2,4-diones; WAT, white adipose tissue; Z, Zusammen; i.m, Intramuscular; mCPBA, meta-chloroperoxybenzoic acid

Year:  2020        PMID: 32154036      PMCID: PMC7052407          DOI: 10.1016/j.jare.2020.01.008

Source DB:  PubMed          Journal:  J Adv Res        ISSN: 2090-1224            Impact factor:   10.479


  86 in total

Review 1.  Thiazolidinediones in the treatment of insulin resistance and type II diabetes.

Authors:  A R Saltiel; J M Olefsky
Journal:  Diabetes       Date:  1996-12       Impact factor: 9.461

2.  Novel euglycemic and hypolipidemic agents. 1.

Authors:  B B Lohray; V Bhushan; B P Rao; G R Madhavan; N Murali; K N Rao; A K Reddy; B M Rajesh; P G Reddy; R Chakrabarti; R K Vikramadithyan; R Rajagopalan; R N Mamidi; H K Jajoo; S Subramaniam
Journal:  J Med Chem       Date:  1998-05-07       Impact factor: 7.446

3.  Design, synthesis and molecular docking of thiazolidinedione based benzene sulphonamide derivatives containing pyrazole core as potential anti-diabetic agents.

Authors:  Mohd Javed Naim; Ozair Alam; Md Jahangir Alam; Md Quamrul Hassan; Nadeem Siddiqui; V G M Naidu; Md Iqbal Alam
Journal:  Bioorg Chem       Date:  2017-11-16       Impact factor: 5.275

4.  The effect of intensive treatment of diabetes on the development and progression of long-term complications in insulin-dependent diabetes mellitus.

Authors:  D M Nathan; S Genuth; J Lachin; P Cleary; O Crofford; M Davis; L Rand; C Siebert
Journal:  N Engl J Med       Date:  1993-09-30       Impact factor: 91.245

5.  Synthesis, characterization, biological evaluation and docking of coumarin coupled thiazolidinedione derivatives and its bioisosteres as PPARγ agonists.

Authors:  Shubhanjali Shukla; Pankaj Kumar; Nirupam Das; N S Hari Narayana Moorthy; Sushant Kumar Shrivastava; Piyush Trivedi; Radhey Shyam Srivastava
Journal:  Med Chem       Date:  2012-09       Impact factor: 2.745

6.  Comparison of vildagliptin and thiazolidinedione as add-on therapy in patients inadequately controlled with metformin: results of the GALIANT trial--a primary care, type 2 diabetes study.

Authors:  L Blonde; S Dagogo-Jack; M A Banerji; R E Pratley; A Marcellari; R Braceras; D Purkayastha; M Baron
Journal:  Diabetes Obes Metab       Date:  2009-07-13       Impact factor: 6.577

7.  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.

Authors:  Syed Nazreen; Mohammad Sarwar Alam; Hinna Hamid; Mohammad Shahar Yar; Abhijeet Dhulap; Perwez Alam; M A Q Pasha; Sameena Bano; Mohammad Mahboob Alam; Saqlain Haider; Chetna Kharbanda; Yakub Ali; K K Pillai
Journal:  Bioorg Med Chem Lett       Date:  2014-05-22       Impact factor: 2.823

8.  A Multicenter Observational Study of Incretin-based Drugs and Heart Failure.

Authors:  Kristian B Filion; Laurent Azoulay; Robert W Platt; Matthew Dahl; Colin R Dormuth; Kristin K Clemens; Nianping Hu; J Michael Paterson; Laura Targownik; Tanvir C Turin; Jacob A Udell; Pierre Ernst
Journal:  N Engl J Med       Date:  2016-03-24       Impact factor: 91.245

9.  Association Between Incretin-Based Drugs and the Risk of Acute Pancreatitis.

Authors:  Laurent Azoulay; Kristian B Filion; Robert W Platt; Matthew Dahl; Colin R Dormuth; Kristin K Clemens; Madeleine Durand; Nianping Hu; David N Juurlink; J Michael Paterson; Laura E Targownik; Tanvir C Turin; Pierre Ernst; Samy Suissa; Colin R Dormuth; Brenda R Hemmelgarn; Gary F Teare; Patricia Caetano; Dan Chateau; David A Henry; J Michael Paterson; Jacques LeLorier; Adrian R Levy; Pierre Ernst; Robert W Platt; Ingrid S Sketris
Journal:  JAMA Intern Med       Date:  2016-10-01       Impact factor: 21.873

10.  Combination Therapy With Exenatide Plus Pioglitazone Versus Basal/Bolus Insulin in Patients With Poorly Controlled Type 2 Diabetes on Sulfonylurea Plus Metformin: The Qatar Study.

Authors:  Muhammad Abdul-Ghani; Osama Migahid; Ayman Megahed; John Adams; Curtis Triplitt; Ralph A DeFronzo; Mahmoud Zirie; Amin Jayyousi
Journal:  Diabetes Care       Date:  2017-01-17       Impact factor: 19.112

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  5 in total

1.  Thiazolidine-2,4-dione derivative exhibits antitumoral effect and reverts behavioral and metabolic changes in a model of glioblastoma.

Authors:  Alana de Vasconcelos; Larissa Ribeiro de Moura; Nathalia Stark Pedra; Natália Pontes Bona; Mayara Sandrielly Pereira Soares; Magno da Silva Marques; Ana Paula Horn; Luiza Spohr; Roselia Maria Spanevello; Francieli Moro Stefanello; Wilson Cunico
Journal:  Metab Brain Dis       Date:  2022-05-26       Impact factor: 3.655

Review 2.  The forgotten type 2 diabetes mellitus medicine: rosiglitazone.

Authors:  Bo Xu; Aoxiang Xing; Shuwei Li
Journal:  Diabetol Int       Date:  2021-06-29

Review 3.  Fighting the Host Reaction to SARS-COv-2 in Critically Ill Patients: The Possible Contribution of Off-Label Drugs.

Authors:  Stefania Scala; Roberto Pacelli
Journal:  Front Immunol       Date:  2020-05-27       Impact factor: 7.561

Review 4.  Thiazolidin-2,4-Dione Scaffold: An Insight into Recent Advances as Antimicrobial, Antioxidant, and Hypoglycemic Agents.

Authors:  Harsh Kumar; Navidha Aggarwal; Minakshi Gupta Marwaha; Aakash Deep; Hitesh Chopra; Mohammed M Matin; Arpita Roy; Talha Bin Emran; Yugal Kishore Mohanta; Ramzan Ahmed; Tapan Kumar Mohanta; Muthupandian Saravanan; Rakesh Kumar Marwaha; Ahmed Al-Harrasi
Journal:  Molecules       Date:  2022-10-10       Impact factor: 4.927

Review 5.  Thiazolidinediones: An In-Depth Study of Their Synthesis and Application to Medicinal Chemistry in the Treatment of Diabetes Mellitus.

Authors:  Nathan Long; Adam Le Gresley; Stephen P Wren
Journal:  ChemMedChem       Date:  2021-05-04       Impact factor: 3.466

  5 in total

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