Journal of medicinal chemistry

Design and synthesis of tetrahedral intermediate analogs as potential dihydroorotase inhibitors

CH Levenson, RB Meyer Jr

Index: Levenson, Corey H.; Meyer, Rich B. Journal of Medicinal Chemistry, 1984 , vol. 27, # 2 p. 228 - 232

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Citation Number: 32

Abstract

Three new heterocyclic analogues (4-6) of dihydroorotic acid were designed, synthesized, and tested as inhibitors of dihydroorotase. Each compound possessed a tetrahedral sulfur atom at the position equivalent to carbon 4 in the dihydroorotate ring in an attempt to mimic the presumed tetrahedral transition state in the course of the enzymatic reaction. Additionally, N-carbamyl-3-phosphonoalanine was prepared and evaluated as a ...