Novel glitazones: Design, synthesis, glucose uptake and structure-activity relationships

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 6, 2010, Pages 1953-1956

  Kumar, B R Prashantha ^a   Nanjan, M J ^a  

^a JSS COLLEGE OF PHARMACY   (India)

Author keywords

Antidiabetic activity; Diabetes; Glitazones; Glucose uptake; PPAR

Indexed keywords

2,4 THIAZOLIDINEDIONE DERIVATIVE; ANTIDIABETIC AGENT; GLITAZONE DERIVATIVE; GLUCOSE; INSULIN; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA AGONIST; ROSIGLITAZONE;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; GLUCOSE TRANSPORT; HEMIDIAPHRAGM; IN VITRO STUDY; NONHUMAN; RAT; SCREENING; STRUCTURE ACTIVITY RELATION;

ANIMALS; GLUCOSE; HYPOGLYCEMIC AGENTS; MODELS, MOLECULAR; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLIDINEDIONES;

RATTUS;

EID: 77549084886     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.01.125     Document Type: Article

References (31)

1. Turner N.C. Drug Discovery Today 1 (1996) 109
2. Viberti G.J. Diabetes Complications 19 (2005) 168
3. Wild S., Roglic G., Green A., Sicree R., and King H. Diabetes Care 27 (2004) 1047
4. Alan R.S. Cell 104 (2001) 517
5. Olefsky J.M., and Saltiel A.R. Diabetes 45 (1996) 1661
6. Benardeau A., Benz J., Binggeli A., Blum D., Boehringer M., Grether U., Hilpert H., Kuhn B., Marki H.P., Meyer M., Puntener K., Raab S., Ruf A., Schlatter D., and Mohr P. Bioorg. Med. Chem. Lett. 19 (2009) 2468
7. Maccari R., Ottanà R., Ciurleo R., Rakowitz D., Matuszczak B., Laggner C., and Langer T. Bioorg. Med. Chem. 16 (2008) 5840
8. Janine C., Menciu C., Rakotoarisoa H., Kahn P.H., and Desmurs J.R. Bioorg. Med. Chem. Lett. 9 (1999) 3439
9. Helen D.B., James S.K., and Linda A.J. Diabetes Res. Clin. Pract. 76 (2007) 279
10. Nissen S.E., and Wolski K.N. N. Eng. J. Med. 356 (2007) 2457
11. Peraza M.A., Burdick A.D., Marin H.E., Gonzalez F.J., and Peters J.M. Toxicol. Sci. 90 (2006) 269
12. Michaael L., and Mitchell A.L. Cell 123 (2005) 993
13. Ranjan C., and Ramanujam R. Current Science 8312 (2002) 25
14. Nuss J.M., and Wagman A.S. In: Hagmann (Ed). Annual Reports in Medicinal Chemistry vol. 35 (1999), Academic Press, USA 211-220
15. Kuhn B., Hilpert H., Benz J., Binggeli A., Grether U., Humm R., Maerki H.P., Meyer M., and Mohr P. Bioorg. Med. Chem. Lett. 16 (2006) 4016
16. Sundriyal S., Viswanad B., Bharathy E., Ramarao P., Chakraborti A.K., and Bharatam P.V. Bioorg. Med. Chem. Lett. 18 (2008) 3192
17. Prashantha Kumar B.R., and Nanjan M.J. Indian J. Pharm. Sci. 705 (2008) 565
18. Prashantha Kumar B.R., Desai B.J., Vergheese J., Praveen T.K., Suresh B., and Nanjan M.J. Lett. Drug Design Discovery 5 (2008) 79
19. Prashantha Kumar B.R., Karvekar M.D., Adhikary L., Nanjan M.J., and Suresh B. J. Heterocycl. Chem. 43 (2006) 897
20. Prashantha Kumar B.R., Praveen T.K., Nanjan M.J., Karvekar M.D., and Suresh B. Indian J. Pharmacol. 39 (2007) 299
21. Prashantha Kumar, B. R.; Nanjan, M. J. Med. Chem. Res. 2009, 18 (doi:10.1007/s00044-009-9246-0).
22. +.
23. Walaas E., and Walaas O. J. Biol. Chem. 195 (1952) 367
24. Chattopadhyay R.R., Sarkar S.K., Ganguly S., Banerjee R.N., and Basu T.K. Indian J. Physiol. Pharmacol. 36 (1992) 137
25. Trinder P. Ann. Clin. Biochem. 6 (1964) 24
26. Scand. J. Clin. Lab. Invest. 12 (1960) 402
27. (a) Glucose uptake measurement: Six well microtitre plates were selected for the study with each well capacity of 5 ml (n = 4). Plates were divided into following groups; Group 1: 2 ml of Tyrode solution with 2000 mg/l glucose. Group 2: 2 ml of Tyrode solution with 2000 mg/l glucose and regular insulin (Nova Nardisk, 40 IU/ml) 5 μl containing 0.2 units of insulin. Groups 3-17: 2 ml of Tyrode solution with 2000 mg/l glucose and 2 mg of the test compound 4-18. Group 18: 2 ml of Tyrode solution with 2000 mg/l glucose and 2 mg of rosiglitazone (standard). Groups 19-33: 2 ml of Tyrode solution with 2000 mg/l glucose, regular insulin 5 μl containing 0.2 units of insulin and 2 mg of the test compound 4-18. Group 34: 2 ml of Tyrode solution with 2000 mg/l glucose, regular insulin 5 μl containing 0.2 units of insulin and 2 mg of rosiglitazone (standard). 68 Wistar rats of either sex were maintained on a standard pellet diet, water ad libitum, and fasted overnight. The animals were killed by decapitation and diaphragms were taken out swiftly avoiding trauma and divided into two halves. The hemi-diaphragms were then rinsed in cold Tyrode solution (without glucose) to remove any blood clots and transferred to the respective wells. The plates were closed with the lids and incubated for 45 min at 21 °C with shaking at 60 cycles per min. Following the incubation, the glucose content of the incubated wells was measured by GOD/POD enzymatic method using Merckotest glucose kit and Merck-Microlab 200 analyser.
28. Feige J.N., Gelman L., Michalik L., Desvergne B., and Wahli W. Prog. Lipid Res. 45 (2006) 120
29. Sohda T., Mizuno K., Imamiya E., Sugiyama Y., Fujita T., and Kawamatsu Y. Chem. Pharm. Bull. 30 (1982) 3580
30. Rose D.P., and Connolly J.M. Pharmacol. Ther. 83 (1999) 217
31. SYBYL 6.7, Tripos Inc., 1699 South Hanley Road, St. Louis, MO 631444, USA. www.tripos.com.