Showing papers by "Edward C. Taylor published in 1996"

Synthesis of N-{4-[2-(2-Amino-5,6-dihydro-4(3H)-oxo-7H-pyrrolo[2,3-d]pyrimidin-6-yl)- ethyl]benzoyl}-l-glutamic Acid: A Ring-Contracted Analogue of 5,10-Dideaza-5,6,7,8-tetrahydrofolic Acid†

Abstract: This paper describes the synthesis of N-{4-[2-(2-amino-5,6-dihydro-4(3H)-oxo-7H-pyrrolo[2,3-d]pyrimidin-6-yl)ethyl]benzoyl}-l-glutamic acid (4), which can be viewed as a ring-contracted analogue of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF, 1) in which the C-7 methylene group of the latter has been excised and C-6 joined to N-8. This compound exhibits significant activity as an inhibitor of the growth of human (CCRF-CEM) lymphoblastic leukemic cells in vitro and apparently acts by blocking de novo purine biosynthesis through inhibition of glycinamide ribonucleotide formyltransferase (GAR FTase).

A simplified and efficient synthesis of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF).

Abstract: A new and extremely efficient synthesis of DDATHF from 4-vinylbenzoic acid and bromomalondialdehyde as precursors has been developed which proceeds in 48% overall yield.

Comments on an Attempted Synthesis of 1-Aminocyclopropane-1,2- dicarboxylic Acid.

Abstract: Aminolysis of dimethyl 1-bromocyclopropane-1,2-dicarboxylate in the presence of KHMDS was reinvestigated. Dimethyl 1-methoxycyclopropane-1,2-dicarboxylate instead of the putative dimethyl 1-aminocyclopropane-1,2-dicarboxylate was isolated from the reaction.