Syntheses of. alpha.-and. gamma.-substituted amides, peptides, and esters of methotrexate and their evaluation as inhibitors of folate metabolism

…, JA Montgomery, FM Sirotnak, PL Chello

Index: Piper; Montgomery; Sirotnak; Chello Journal of Medicinal Chemistry, 1982 , vol. 25, # 2 p. 182 - 187

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Citation Number: 75

Abstract

N-[4-[[(Benzyloxy) carbonyl] methylamino] benzoyl]-~-glutamic acid a-benzyl ester (2) and y- benzyl ester (6) served as key intermediates in syntheses of precursors to amides and peptides of methotrexate (MTX) involving both the a-and y-carboxyl groupings of the glutamate moiety. Coupling of 2 and 6 at the open carboxyl grouping with amino compounds was effected by the mixed anhydride method (using isobutyl chloroformate); carboxyl ...