Synthesis and hypoglycemic activity of phenylalkyloxiranecarboxylic acid derivatives
作者:Klaus Eistetter、Horst P. O. Wolf
DOI:10.1021/jm00344a003
日期:1982.2
A series of new 2-(phenylalkyl)oxirane-2-carboxylic acids has been synthesized and studied for its effects on the concentration of blood glucose. Most of the compounds exhibit remarkable blood glucose lowering activities in fasted rats. Structure-activity studies reveal that substituents like Cl or CF3 on the phenyl ring and a chain length of three to five carbon atoms lead to the most effective substances
A copper-catalyzed reaction of a-azidocarbonyl compounds under an oxygen atmosphere is reported where nitriles are formed via C C bond cleavage of a transient Iminyl copper intermediate. The transformation is carried out by a sequence of denitrogenative formation of iminyl copper species from alpha-azidocarbonyl compounds and their C C bond cleavage, where molecular oxygen (1 atm) is a prerequisite to achieve the catalytic process and one of the oxygen atoms of O-2 was found to be incorporated Into the beta-carbon fragment as a carboxylic acid.
GOEL, O. P.;KROLLS, U., TETRAHEDRON LETT., 1983, 24, N 2, 163-166