Synthesis and antifolate evaluation of the aminopterin analogue with a bicyclo [2.2. 2] octane ring in place of the benzene ring

RC Reynolds, CA Johnson, JR Piper…

Index: Reynolds, Robert C; Johnson, Cheryl A; Piper, James R; Sirotnak, Frances M European Journal of Medicinal Chemistry, 2001 , vol. 36, # 3 p. 237 - 242

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Citation Number: 10

Abstract

N-[4-[[2, 4-diamino-6-pteridinyl) methyl] amino] bicyclo [2.2. 2] octane-1-carbonyl]-l-glutamic acid (1) was synthesized and tested for antifolate activity. N-(4-Aminobicyclo [2.2. 2] octane- 1-carbonyl-l-glutamic acid dimethyl ester (6), the side chain precursor to subject compound 1, was synthesized readily via reported bicyclo [2.2. 2] octane-1, 4-dicarboxylic acid monoethyl ester (2). The side chain precursor 6 was alkylated by 6-(bromomethyl)-2, 4- ...