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

Medicinal Chemistry

Volumn 8, Issue 5, 2012, Pages 834-845

  Shukla, Shubhanjali ^a   Kumar, Pankaj ^b   Das, Nirupam ^a   Moorthy, N S Hari Narayana ^b   Shrivastava, Sushant Kumar ^a   Trivedi, Piyush ^b   Srivastava, Radhey Shyam ^a  

^a BANARAS HINDU UNIVERSITY   (India)

^b UNIVERSITY INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Bioisosteres; Diabetes; Imidazolidinedione; Oxazolidinedione; QikProp; Schr dinger; Thiazolidinedione etc.

Indexed keywords

2,4 THIAZOLIDINEDIONE DERIVATIVE; BENZALDEHYDE; COUMARIN; OXAZOLIDINEDIONE DERIVATIVE; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR AGONIST; ROSIGLITAZONE; STREPTOZOCIN;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIDIABETIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ANALYSIS; DRUG SCREENING; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; KNOEVENAGEL CONDENSATION; MALE; MASS SPECTROMETRY; MOLECULAR DOCKING; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RAT;

ANIMALS; BENZALDEHYDES; COMPUTER SIMULATION; COUMARINS; DIABETES MELLITUS, EXPERIMENTAL; ESTERS; HYDANTOINS; HYPOGLYCEMIC AGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MASS SPECTROMETRY; MODELS, MOLECULAR; OXAZOLES; PPAR GAMMA; RATS; RATS, WISTAR; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEREOISOMERISM; STREPTOZOCIN; THIAZOLIDINEDIONES;

EID: 84865797353     PISSN: 15734064     EISSN: 18756638     Source Type: Journal    
DOI: 10.2174/157340612802084388     Document Type: Article

References (29)

1. Dixit, M.; Tripathi, B. K.; Tamrakar, A.K.; Srivastava, A.K.; Kumar, B.; Goel, A. Synthesis of benzofuran scaffold-based potential PTP-1B inhibitors. Bioorg. Med. Chem., 2007, 15(2), 727-734. (Pubitemid 44880728)
2. Yue, E.W.; Wayland, B.; Douty, B.; Crawley, M. L.; Mclaughlin, E.; Takvorian, A.; Wasserman, Z.; Bower, M.J.; Wei, M.; Li, Y.L.; Ala, P. J.; Gonneville, L.; Wynn, R.; Burn, T. C.; Liu, P. C. C.; Combs, A.P. Isothiazolidinone heterocycles as inhibitors of protein tyrosine phosphatases: Synthesis and structure-activity relationships of a peptide scaffold. Bioorg. Med. Chem., 2006, 14(17), 5833-5849. (Pubitemid 44080592)
3. Murthy, V. S.; Kulkarni, V. M. Molecular modeling of protein tyrosine phosphatase 1B (PTP 1B) Inhibitors. Bioorg. Med. Chem., 2002, 10(4), 897-906. (Pubitemid 34139904)
4. Liljebris, C.; Martinsson, J.; Tedenborg, L.; Williams, M.; Barker, E.; Duffy, J. E. S.; Nygren, A.; James, S. Synthesis and Biological Activity of a Novel class of pyridazine analogues as noncompetitive reversible inhibitors of protein tyrosine phosphatase 1B (PTP1B). Bioorg. Med. Chem., 2002, 10(10), 3197-3212. (Pubitemid 34855393)
5. Hastings, K.L.; D.A.B.T, P.H. Thiazolidinedione Hepatotoxicity: The PPAR Paradigm., Office of New Drugs, Center for Drug Evaluation and Research, U.S. Food and Drug Administration.
6. Forman, L.M.; Simmons, D.A.; Diamond, R.H. Hepatic failure in a patient taking rosiglitazone. Ann. Intern. Med., 2000, 132, 118-121. (Pubitemid 30044178)
7. Yoshioka, T.; Fujita, T.; Kanai, T.; Aizawa, Y.; Kurumada, T.; Hasegawa, K.; and 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. (Pubitemid 19061888)
8. Cantello, B. C.; Cawthorne, M. A.; Cottam, G. P.; Duff, P. T.; Haigh, D.; Hindley, R. M.; Lister, C. A.; Snith, S. A.; Thurlby, P. L.[[ω- (Heterocyclylamino) alkoxy] benzyl]-2,4-thiazolidinediones as Potent Antihyperglycemic Agents. J. Med. Chem., 1994, 37(23), 3977-3985. (Pubitemid 24379687)
9. Sohda, T.; Momose, Y.; Meguro, K.; Kawamatsu, Y.; Sugiyama, Y.; Ikeda, H. Studies on antidiabetic agents, synthesis and hypoglycemic activity of 5-[4-(Pyridylalkoxy)benzyl]-2,4 thiazolidinediones. Arzneim. Forsch., 1990, 40, 37-42. (Pubitemid 20037527)
10. Jeon, R.; Park, S.Y. Synthesis and biological activity of benzoxazole containing thiazolidinedione derivatives. Arch. Pharm. Res., 2004, 27(11) 1099-1105.
11. Aronoff, S.; Rosenblatt, S.; Braithwaite, S.; Egan, J.W.; Mathisen, A.L.; and Schneider, R.L. Pioglitazone hydrochloride monotherapy improves glycemic control in the treatment of patients with type 2 diabetes: a 6-month randomized placebo-controlled dose-response study. The Pioglitazone 001 Study Group. Diabetes Care, 2000, 23(11), 1605-1611.
12. Inzucchi, S.E. Oral antihyperglycemic therapy for type 2 diabetes. J. Am. Med. Assoc., 2002, 287, 360-372. (Pubitemid 34256388)
13. Parulkar, A.A.; Pendergrass, M.L.; Ayala, R. G.; Lee, T.R.; Fonseca, V.A. Nonhypoglycemic Effects of thiazolidinediones. Ann. Intern. Med., 2001, 134, 61-71. (Pubitemid 32037344)
14. Actos Prescribing Information.Takeda Chemical Industries Ltd, Osaka, Japan, 2002.
15. 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-M activators. Bioorg. Med. Chem. Lett., 2010, 20(22), 6758-6763.
16. Kennedy, E. L.; Tchao, R.; Harvison, P. J. Nephrotoxic and hepatotoxic potential of imidazolidinedione, oxazolidinedione- and thiazolidinedione- containing analogues of N-(3,5-dichloro phenyl) succinimide (NDPS) in Fischer 344 rats. Toxicol. 2003, 186(1-2), 79-91. (Pubitemid 36246621)
17. Houcine, A.; Souhir; A.; Forgue, S. F. Synthesis and spectroscopic study of new biscoumarin dyes based on 7-(4-methylcoumarinyl) diesters. Dyes Pigm. 2008, 78(1), 1-7.
18. Li, X.; Jain, N.K.; Russell, R.K.; Ma, R.; Branum, S.; Xu, J.; Sui, Z. Development of a scalable synthetic process for selective bromination of 4-Methyl-3,7-Substituted Coumarins Org. Process Res. Dev., 2006, 10(2), 354-360. (Pubitemid 43508451)
19. Ghate, M.; Manohar, D.; Kulkarni, V.; Shobha R.; Kattimani, S.Y. Synthesis of vanillin ethers from 4-(bromomethyl) coumarins as anti-inflammatory agents. Eur. J. Med. Chem., 2003, 38(3), 297-302. (Pubitemid 36349672)
20. 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-thiazolidine- dione. Eur. J. Med. Chem., 2004, 39(5), 433-447. (Pubitemid 38526360)
21. Adisakwattana, S.; Roengsamran, S.; Hsu, W. H.; Yibchokanun, S. Mechanisms of antihyperglycemic effect of p-methoxycinnamic acid in normal and streptozotocin-induced diabetic rats., Life Sci., 2005, 78(4), 406-412. (Pubitemid 41597550)
22. Henke, B.R.; Adkison, K.K.; Blanchard, S.G.; Leesnitzer, L.M.; Mook, R.A.; Plunker, K.D.; Ray, J.A.; Roberson, C.R.; Unwalla, R.; Willson, T.M.; Synthesis and biological activity of a novel series of indole derived PPARM agonists. Bioorg. Med. Chem. Lett., 1999, 9(23), 3329-3334.
23. Nomura, M.; Kinoshita, S.; Satoh, H.; Maeda, T.; Murakami, K.; Tsunoda, M.; Miyachi, H.; Awano, K. (3-Substituted Benzyl) thiazolidine-2,4-diones as structurally new antihyperglycemic Agents. Bioorg. Med. Chem. Lett., 1999, 9(4), 533-538. (Pubitemid 29090646)
24. Dundar, O.B.; Verspohl, E.J.; Evcimen, N.D.; Kaup, R.M.; Bauer, K.; Sarikaya, M.; Evranos, B.; Ertan, R. Synthesis and biological activity of some new flavonyl-2,4-thiazolidinediones. Bioorg. Med. Chem., 2008, 16(14), 6747-6751.
25. Kuhn, B.; Hilpert, H.; Benz, J.; Binggeli, A.; Grether, U.; Humm, R.; Marki, H.P.; Meyer, M.; Mohr, P. Structure-based design of indole propionic acids as novel PPAR α/γ co-agonists. Bioorg. Med. Chem. Lett., 2006, 16(15), 4016-4020. (Pubitemid 43903212)
26. http://www.rcsb.org/pdb/.
27. Halgren, T. A.; Murphy, R. B.; Friesner, R. A.; Beard, H. S.; Frye, L. L.; Pollard, W. T.; & Banks, J. L. Glide: a new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening. J. Med. Chem., 2004, 47(7), 1750-1759. (Pubitemid 38380918)
28. Sengupta, D.; Verma, D.; Naik, P.K. Docking mode of delvardine and its analogues into the p66 domain of HIV-1 reverse transcriptase: screening using molecular mechanics generalized born/surface area and absorption, distribution, metabolism and excretion properties. J. Biosci., 2007, 32, 1307-1316.
29. Moorthy N.S.H.N.; Karthikeyan C.; Trivedi P. Synthesis, cytotoxic evaluation and in silico pharmacokinetic prediction of some benzo[a]phenazine-5- sulfonic acid derivatives. Med. chem., 2009, 5(6), 549-557.