Synthesis and structure-activity relationship studies of cinnamic acid-based novel thiazolidinedione antihyperglycemic agents

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 18, 2003, Pages 4059-4067

  Neogi, Partha ^a   Lakner, Fredrick J ^a   Medicherla, Satyanarayana ^a   Cheng, Jin ^a   Dey, Debendranath ^a   Gowri, Maya ^a   Nag, Bishwajit ^b   Sharma, Somesh D ^b   Pickford, Lesley B ^a   Gross, Coleman ^a  

^a Calyx Therapeutics Inc   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

2,4 THIAZOLIDINEDIONE DERIVATIVE; 3 (3,5 DIMETHOXYPHENYL) 2 (4 HYDROXYPHENYL)PROPIONIC ACID METHYL ESTER; 3 (3,5 DIMETHOXYPHENYL) 2 [4 [4 (2,4 DIOXOTHIAZOLIDIN 5 YLIDENMETHYL)PHENOXY]PHENYL]ACRYLIC ACID METHYL ESTER; 3 (3,5 DIMETHOXYPHENYL) 2 [4 [4 (2,4 DIOXOTHIAZOLIDIN 5 YLIDENMETHYL)PHENOXY]PHENYL]PROPIONIC ACID METHYL ESTER; 3 (3,5 DIMETHOXYPHENYL) 2 [4 [4 (2,4 DIOXOTHIAZOLIDIN 5 YLMETHYL)PHENOXY]PHENYL]ACRYLIC ACID; 3 (3,5 DIMETHOXYPHENYL) 2 [4 [4 (2,4 DIOXOTHIAZOLIDIN 5 YLMETHYL)PHENOXY]PHENYL]ACRYLIC ACID METHYL ESTER; 3 (3,5 DIMETHOXYPHENYL) 2 [4 [4 (2,4 DIOXOTHIAZOLIDIN 5 YLMETHYL)PHENOXY]PHENYL]PROPIONIC ACID METHYL ESTER; ANTIDIABETIC AGENT; CINNAMIC ACID; GLUCOSE; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; PHENYL GROUP; PIOGLITAZONE; ROSIGLITAZONE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DISEASE MODEL; DRUG EFFECT; DRUG MECHANISM; DRUG METABOLISM; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME INHIBITION; GLUCOSE BLOOD LEVEL; GLUCOSE METABOLISM; HUMAN; HUMAN CELL; ISOMER; MOUSE; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; STRUCTURE ACTIVITY RELATION;

RODENTIA;

EID: 0043092029     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00393-6     Document Type: Article

References (25)

1. Harris M.I., Flegal K.M., Cowie C.C., Eberhardt M.S., Goldstein D.E., Little R.R., Weideyer H.M., Byrd-Holt D.D. Diabetes Care. 21:1998;518.
2. Howard B.V. Int. Congr. Ser. 1100:1995;446.
3. Bennet P.H. Diabet. Metab. Rev. 13:1997;583.
4. (a) Reaven G.M. Diabetes. 37:1988;1595
5. (b) Reaven G.M. Diabetes. 2(Suppl.):2000;S274.
6. Gerich J.E. N. Engl. J. Med. 321:1989;1231.
7. Wiernsperger N.F., Baily C.J. Drugs. 58:1999;31.
8. Schmid-Antomarchi H.S., De Weille J., Fosset M., Lazdunski M. J. Biol. Chem. 262:1987;15840.
9. (a) Ferner R.E., Neil H.A.W. Br. Med. J. 269:1988;949
10. (b) Burge M.R., Sood V., Sobhy T.A., Rassam A.G., Schade D.S. Diabetes, Obes. Metab. 1:1999;199.
11. Schoonjans K., Auwerx J. The Lancet. 355:2000;1008.
12. Nuclear Receptors Nomenclature Commitee. Cell 1999, 97, 97-161.
13. Lehmann J.M., Moore L.B., Smith-Oliver T.A., Wilkinson W.O., Wilson T.M., Kliewer S.A. J. Biol. Chem. 270:1995;12953.
14. Shoda T., Mizuno K., Imamiya E., Sugiyama Y., Fujita T., Kawamatsu Y. Chem. Pharm. Bull. 30:1982;3580.
15. Mosome Y., Meguro K., Ikeda H., Hatanaka C., Ot S., Shoda T. Chem. Pharm. Bull. 39:1991;1440.
16. (a) Cantello B.C.C., Cawthorne M.A., Haig D., Hindley R.M., Smith S.A., Thurlby P.L. Bioorg. Med. Chem. Lett. 4:1994;1181
17. (b) Cantello B.C.C., Cawthorne M.A., Cottam G.P., Duff P.T., Haig D., Hindley R.M., Lister C.A., Smith S.A., Thurlby P.L. J. Med. Chem. 37:1994;3977.
18. Dey D., Neogi P., Nag B. FASEB J. 15:2001;A526.
19. Dey D., Medicherla S., Neogi P., Nag B. Diabetes. 48:1999;A119.
20. Pettit G.R., Singh S.B., Schmidt J.M., Niven M.L., Hamel E., Lin C.M. J. Nat. Prod. 51:1998;517.
21. (a) Hudlicky M. ACS Monograph 188. 1996;ACS, Washington, DC. p 46
22. (b) Ram S., Ehrenkaufer R.E. Synthesis. 1988;91.
23. Kessar S.V., Nadir U.K., Gupta Y.P., Pahwa P.S., Singh P. Indian J. Chem. 20B:1981;1.
24. Dey, D.; Medicherla, S.; Neogi, P.; Gowri, M.; Cheng, J.; Gross, C.; Sharma, S. D.; Reaven, G. M.; Nag, B. Metabolism. In press.
25. Sen A., Rydzewski J., Subramaniam K., Gross C. AAPS Pharm. Sci. 4:2002;M1290.