Synthesis and in vivo antidiabetic activity of novel dispiropyrrolidines through [3 + 2] cycloaddition reactions with thiazolidinedione and rhodanine derivatives

European Journal of Medicinal Chemistry

Volumn 44, Issue 8, 2009, Pages 3272-3279

  Murugan, Ramalingam ^a   Anbazhagan, S ^b   Sriman Narayanan, S ^c  

^a Orchid Research Laboratories Limited   (India)

^b C L BAID METHA COLLEGE OF PHARMACY   (India)

^c UNIVERSITY OF MADRAS   (India)

Author keywords

1,3 Dipolar cycloaddition; Antidiabetic; Rhodanine; Thiazolidinedione

Indexed keywords

2,4 THIAZOLIDINEDIONE DERIVATIVE; 5 (2,4 DIOXO 5 THIAZOLIDINYLMETHYL) 2 METHOXY N [4 (TRIFLUOROMETHYL)BENZYL]BENZAMIDE; ALLOXAN; DISPIROPYRROLIDINE DERIVATIVE; FARGLITAZAR; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; PIOGLITAZONE; PYRROLIDINE DERIVATIVE; RHODANINE; RIVOGLITAZONE; ROSIGLITAZONE; UNCLASSIFIED DRUG;

ALANINE AMINOTRANSFERASE BLOOD LEVEL; ALKALINE PHOSPHATASE BLOOD LEVEL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIDIABETIC ACTIVITY; ARTICLE; CONTROLLED STUDY; CREATININE BLOOD LEVEL; CRYSTAL STRUCTURE; CYCLOADDITION; DIABETES MELLITUS; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; GLUCOSE BLOOD LEVEL; IN VIVO STUDY; MALE; MOLECULAR DOCKING; NONHUMAN; RAT; STEREOCHEMISTRY; UREA NITROGEN BLOOD LEVEL;

ANIMALS; BLOOD GLUCOSE; DIABETES MELLITUS; DRUG DESIGN; HUMANS; HYPOGLYCEMIC AGENTS; INSULIN; LIGANDS; MALE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PYRROLIDINES; RATS; RATS, WISTAR; RHODANINE; THIAZOLIDINES;

EID: 67349138213     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.03.035     Document Type: Article

References (50)

1. Turner N.C. Drug Discovery Today 1 (1996) 103-108
2. King H., Aubert R.E., and Herman W.H. Diabetes Care 21 (1998) 1414-1431
3. Rotella D.P. J. Med. Chem. 47 (2004) 4111-4112
4. DeFronzo R.A., Bonadonna R.C., and Ferrannini E. Diabetologia 35 (1992) 389-397
5. Lebovitz H.E. Clinician's Mannual on Insulin Resistance (2002), London Science Press Ltd, London
6. Groop L., and Orho-Melander M. J. Int. Med 250 (2001) 105-120
7. DeFronzo R.A., Bonadonna R.C., and Ferrannini E. Diabetes Care 15 (1992) 318-368
8. Saltiel A.R., and Olefsky J.M. Diabetes 45 (1996) 1661-1669
9. Frances C.B. Chem. Rev. 61 (1961) 463-521
10. Fonseca V., Rosenstock J., Patwardhan R., and Salzman A. J. Am. Med. Assoc. 283 (2000) 1695-1702
11. Sing W.T., Lee C.L., Yeo S.L., Lim S.P., and Sim M.M. Bioorg. Med. Chem. Lett. 11 (2001) 91-94
12. Momose Y., Meguro K., Ikeda H., Hatanaka C., Oi S., and Sohada T. Chem. Pharm. Bull. 39 (1991) 1440-1445
13. Fujishima H., and Tuboto K. Br. J. Ophthalmol. 86 (2002) 860-865
14. Grant E.B., Guiadeen D., Baum E.Z., Foleno B.D., Jin H., Montenegro D.A., Nelson E.A., Bush K., and Hlasta D.J. Bioorg. Med. Chem. Lett. 10 (2000) 2179-2181
15. Free C.A., Majchrowich E., and Hess S.M. Biochem. Pharmacol. 20 (1971) 1421-1428
16. Cutshall N.S., O'Day C., and Prezhdo M. Bioorg. Med. Chem. Lett. 15 (2005) 3374-3379
17. Ram V.J. Drugs Today 39 (2003) 609-632
18. Lehmann J.M., Moore L.B., Smith Oliver T.A., Wilkinson W.O., Willson T.M., and Kliewer S.A. J. Biol. Chem. 270 (1995) 12953-12956
19. Lambe K.G., and Tugwood J.D. Eur. J. Biochem. 239 (1996) 1-7
20. Berger J., Bailey P., Biswas C., Cullinan C.A., Doebber W., Hayes N.S., Sapestein R., Smith R.G., and Leibowitz M.D. Endocrinology 137 (1996) 4189-4195
21. Nomura M., Kinoshita S., Satoh H., Maeda T., Murakami K., Tsunoda M., Miyachi H., and Awano K. Bioorg. Med. Chem. Lett. 9 (1999) 533-538
22. In: Tsuge O., Kanemasa S., and Katritzky A.R. (Eds). Advances in Heterocyclic Chemistry (1989), Academic, San Diego, CA
23. In: Padwa A. (Ed). 1,3-Dipolar Cycloaddition Chemistry vols. 1 and 2 (1984), Wiley, New York, NY
24. In: Grigg R., Sridharan V., and Curran D.P. (Eds). Advances in Cycloaddition (1993), Jai, London
25. Kozikowski A.P. Acc. Chem. Res. 17 (1984) 410-416
26. Howe R.K., and Shelton B.R. J. Org. Chem. 55 (1990) 4603-4607
27. De Amici M., De Michelli C., and Misani V. Tetrahedron 46 (1990) 1975-1986
28. V.L. Cohen, E.E. Kleinmann, PCT. Int. Appl. W.O. 24 (1995) 398.
29. Caroll W.A., and Grieco P.A. J. Am. Chem. Soc. 115 (1993) 1164-1165
30. Earley W.G., Oh T., and Overman L.E. Tetrahedron Lett. 29 (1988) 3785-3788
31. Ban Y., Taga N., and Oishi T. Tetrahedron Lett. 2 (1974) 187-190
32. Van Tamelen E.E., Yardley J.P., Miyano M., and Hinshaw Jr. W.B. J. Am. Chem. Soc. 26 (1969) 7333-7341
33. Grigg R., Suredrakumar S., Thianpatanagul S., and Vipond D.J. J. Chem. Soc., Perkin Trans. 1 (1988) 2693-2770
34. Grigg R., Idle J., McMeekin P., and Vipond D.J. J. Chem. Soc., Perkin Trans. 1 (1988) 2703-2713
35. Volhard J.J. J. Prakt. Chem. 9 (1874) 217-224
36. Charles K.B., and Frances C.B. J. Am. Chem. Soc. 78 (1956) 6189-6192
37. Nencki M.J. J. Prakt. Chem. 16 (1877) 2-22
38. Shepherd R.G. J. Org. Chem. 12 (1947) 275-283
39. Amal Raj A., and Raghunathan R. Tetrahedron 57 (2001) 10293-10298
40. Amal Raj A., Raghunathan R., Sridevikumari M.R., and Raman N. Bioorg. Med. Chem. 11 (2003) 407-419
41. Diller D.J., and Merz Jr. K.M. Proteins 43 (2001) 113-124
42. Khanna S., Sobhia M.E., and Bharatam P.V. J. Med. Chem. 48 (2005) 3015-3025
43. Ramachandran U., Mital A., Bharatam P.V., Khanna S., Rao P.R., Srinivasan K., Kumar R., Chawla H.P.S., Kaul C.L., Raichur S., and Chakrabarti R. Bioorg. Med. Chem. 12 (2004) 655-662
44. Reginato M.J., Bailey S.T., Krakow S.L., Minami C., Ishii S., Tanaka H., and Lazar M.A. J. Biol. Chem. 273 (1998) 32679-32684
45. Fukui Y., Masui S.I., Osada S., Umesono K., and Motojima K. Diabetes 49 (2000) 759-767
46. Lohary B.B., Bhushan V., Reddy A.S., Rao P.B., Reddy N.J., Harikishore P., Haritha N., Vikramadityan R.K., Chakrabarati R., Rajagopalan R., and Katneni K. J. Med. Chem. 42 (1999) 2569-2581
47. Liver damage warning for troglitazone. Scrip 21 (1997) 2282-2285
48. In: Varley H., Gowenlock A.H., and Bell M. (Eds). Practical Clinical Biochemistry (1980), William Heinemann Medical Books Ltd, London
49. Cooperstien S.J., and Walkins D. The Islets of Langerhans (1981), Academic Press, New York pp. 387
50. Perfumi M., and Tacconi R. Int. J. Pharm. 34 (1996) 41-47