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6544586 
Journal Article 
Synthesis, structure and hypocholesterolemic activity of a series of substituted 4-aryl, 4-oxo butyric acids 
Cousse, H; Mouzin, G; Rieu, JP; Delhon, A; Bruniquel, F; Fauran, F 
1987 
Yes 
European Journal of Medicinal Chemistry
ISSN: 0223-5234
EISSN: 1768-3254 
22 
1 
45-57 
French 
WOS:A1987G951300008 
A series of substituted 4-biphenyl, 2 or 3-methylene 4-oxo butyric acids, their isomers and acids selectively reduced on carbonyl and double bond were synthesized and their hypolipidemic actions were comparatively tested. Substitution on biphenyl by chlorine in position 2′ gave the derivative with maximal effect (itanoxone 1h). 4-Keto, 2-butenoic acid isomers and their hydrogenated homologues presented good activity when the methyl group was in position 2 of the aliphatic chain (compounds 3, 5 et 6). Esters, and mainly amide derivatives, were less active. Partial or total reduction of carbonyl into alcohol or CH2 gave acids which were half as active, except for 4-hydroxy, 2-methylene butyric acids which were inactive. Itanoxone 1h can be considered as the prototype of a new class of hypocholesterolemic substances. 
itanoxone; metbufene; hypocholesterolemic; structure—activity