Molecular Design, Synthesis, and Hypoglycemic Activity of a Series of Thiazolidine-2,4-diones
A series of imidazopyridine thiazolidine-2,4-diones were designed and synthesized from their corresponding pyridines. These compounds represent conformationally restricted analogues of the novel hypoglycemic compound rosiglitazone (5). The series was evaluated for its effect on insulin-induced 3T3-L...
Saved in:
Published in | Journal of medicinal chemistry Vol. 43; no. 16; pp. 3052 - 3066 |
---|---|
Main Authors | , , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
10.08.2000
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Summary: | A series of imidazopyridine thiazolidine-2,4-diones were designed and synthesized from their corresponding pyridines. These compounds represent conformationally restricted analogues of the novel hypoglycemic compound rosiglitazone (5). The series was evaluated for its effect on insulin-induced 3T3-L1 adipocyte differentiation in vitro and its hypoglycemic activity in the genetically diabetic KK mouse in vivo. The structure−activity relationships are discussed. On the basis of the in vivo potency, 5-[4-(5-methoxy-3-methyl-3H-imidazo[4,5-b]pyridin-2-ylmethoxy)benzyl]thiazolidine-2,4-dione (19a) was selected as the candidate for further studies in a clinical setting. |
---|---|
Bibliography: | ark:/67375/TPS-VDTXJNC3-K istex:5E9AB2AE4C09F1B5A6EE16644F5C787F4686F4AC |
ISSN: | 0022-2623 1520-4804 |
DOI: | 10.1021/jm990522t |