QUANTITATIVE STRUCTURE-ACTIVITY-RELATIONSHIPS INVOLVING THE INHIBITION OF GLYCOLIC ACID OXIDASE BY DERIVATIVES OF GLYCOLIC AND GLYOXYLIC ACIDS

被引：19

作者：

RANDALL, WC ^{[1
]}

STREETER, KB ^{[1
]}

CRESSON, EL ^{[1
]}

SCHWAM, H ^{[1
]}

MICHELSON, SR ^{[1
]}

ANDERSON, PS ^{[1
]}

CRAGOE, EJ ^{[1
]}

WILLIAMS, HWR ^{[1
]}

EICHLER, E ^{[1
]}

ROONEY, CS ^{[1
]}

机构：

[1] MERCK FROSST LABS,POINTE CLAIRE H9R 4P8,QUEBEC,CANADA

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1979年 / 22卷 / 06期

关键词：

D O I：

10.1021/jm00192a002

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The enzyme glycolic acid oxidase oxidizes glycolate to glyoxylate and glyoxylate to oxalate. Three series of compounds related to the natural substrates, substituted glycolic, oxyacetic, and glyoxylic acids, have been investigated as inhibitors of this enzyme using the techniques of regression analysis and quantitative structure-activity relationships. The best overall correlation with inhibitory potencies was found with the Hansch hydrophobic parameter π. The classical electronic parameters σp, σmℐ, and ℛ performed poorly. For the substituted glyoxylic acids, a dummy parameter relating to the presence of a nucleophilic group in close proximity to the-carbonyl of the glyoxylate group was found to be highly significant. The syntheses of six novel glycolic and glyoxylic acids are described. © 1979, American Chemical Society. All rights reserved.

引用

页码：608 / 614

页数：7

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