Journal of Medicinal Chemistry p. 2617 - 2626 (1992)
Update date:2022-08-04
Topics:
Sohda
Mizuno
Momose
Ikeda
Fujita
Meguro
In the course of further chemical modification of the novel antidiabetic pioglitazone (AD-4833, U-72, 107), a series of 5-[4-(2- or 4- azolylalkoxy)benzyl- or -benzylidene]-2,4-thiazolidinediones was prepared and evaluated for hypoglycemic and hypolipidemic activities in insulin-resistant, genetically obese, and diabetic KKA(y) mice. Replacement of the 2-pyridyl moiety of pioglitazone by a 2- or 4-oxazolyl or a 2- or 4-thiazolyl moiety greatly enhanced in vivo potency. The corresponding 5-benzylidene-type compounds, in which a methine was used as a linker between the benzene ring and the thiazolidinedione ring, also had potent biological activity. Among the compounds synthesized, 5-[4-[2-(5-methyl-2-phenyl-4- oxazolyl)ethoxy]benzyl]-2,4-thiazolidinedione (18) exhibited the most potent activity, more than 100 times that of pioglitazone. The synthesis and structure-activity relationships for this novel series of derivatives are detailed.
View MoreJiacheng-Chem Enterprises Limited
Contact:86-571-86711508
Address:19 Floor, CIBC Holley International Building, No. 198,Wuxing Road, Hangzhou, China,310020
Nantong Baokai Chemical Co., Ltd (Hangzhou Baokai Bio-Chemicals Co.,Ltd.)
Contact:+86-513-83886111
Address:No. 68 Suzhou road ,Binjiang Fine Chemical Industrial Park , Beixin town, Qidong city ,Jiangsu province
website:http://www.orchid-chem.com
Contact:+86-571-85395792
Address:607, North Zhongshan Road, Hangzhou 310000 China
Shanghai birch chemical technology co.,ltd
Contact:+86-21-54096810
Address:No.2588,Jungong Road,Shanghai,China
CGeneTech (Suzhou, China) Co., Ltd.
Contact:+86-512-62956962
Address:Room 101,Bld C11,218 Xinghu Rd.,Suzhou industrial Park
Doi:10.1039/c19660000650
(1966)Doi:10.1016/j.bmc.2006.11.007
(2007)Doi:10.1021/acs.joc.0c00915
(2020)Doi:10.1002/chem.201304240
(2014)Doi:10.1016/S0031-9422(00)88465-4
(1972)Doi:10.1002/ddr.21726
(2020)