Folate analogs altered in the C9-N10 bridge region. 18. Synthesis and antitumor evaluation of 11-oxahomoaminopterin and related compounds

…, RL Kisliuk, Y Gaumont, FM Sirotnak

Index: Nair; Bridges; Henkel; Kisliuk; Gaumont; Sirotnak Journal of Medicinal Chemistry, 1981 , vol. 24, # 9 p. 1068 - 1073

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Citation Number: 16

Abstract

The chemical synthesis of 11-oxahomoaminopterin (1) has been carried out using procedures which were also found to be applicable to the synthesis of 11-oxahomofolic acid (2). Reaction of l-bromo-4-[p-(carbomethoxy) phen-oxy]-% butanone (10) with sodium azide gave l-azido-4-[p-(carbomethoxy) phenoxy]-2-butanone (1 1). Protection of the carbonyl group of 11 as the ethylene ketal and subsequent base hydrolysis of the product gave l- ...