Methotrexate analogs. 33. N. delta.-acyl-N. alpha.-(4-amino-4-deoxypteroyl)-L-ornithine derivatives. Synthesis and in vitro antitumor activity

A Rosowsky, H Bader, CA Cucchi…

Index: Rosowsky, Andre; Bader, Henry; Cucchi, Carol A.; Moran, Richard G.; Kohler, William; Freisheim, James H. Journal of Medicinal Chemistry, 1988 , vol. 31, # 7 p. 1332 - 1337

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Citation Number: 47

Abstract

N*-Acyl derivatives of the potent folylpolyglutamate synthetase (FPGS) inhibitor Nm-(4- amino-4-deoxypteroy1)-L-ornithine (APA-L-Om) were synthesized from N~-(4-amino-4- deoxy-N10-formylpteroyl)-~-ornithine by reaction with an N-(acy1oxy) succinimide or acyl anhydride, followed by deformylation with base. The N*-hemiphthaloyl derivative was also prepared from 4-amino-4-deoxy-N10-formylpteroic acid by reaction with persilylated N6- ...