Synthesis and antitumor activity of 10-alkyl-10-deazaminopterins. A convenient synthesis of 10-deazaminopterin

…, H Tagawa, RL Kisliuk, Y Gaumont…

Index: DeGraw; Brown; Tagawa; Kisliuk; Gaumont; Sirotnak Journal of Medicinal Chemistry, 1982 , vol. 25, # 10 p. 1227 - 1230

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Citation Number: 64

Abstract

Requirements for large-scale synthesis of the potent antitumor drug 10-deazaminopterin have led to development of a facile synthesis of this compound and its 10-alkyl analogues. The lithium diisopropyl amide generated dianions of appropriate p-alkylbenzoic acids were alkylated with 3-methoxyallyl chloride. The resulting 4-(p-carboxy-phenyl)-1-methoxy-1- butenes were brominated at pH 7-8 to afford the 2-bromo-4-(p-carboxyhenyl) ...