Plasmin-activated prodrugs for cancer chemotherapy. 1. Synthesis and biological activity of peptidylacivicin and peptidylphenylenediamine mustard

…, PL Carl, MJ Weber, JA Katzenellenbogen

Index: Chakravarty; Carl; Weber; Katzenellenbogen Journal of Medicinal Chemistry, 1983 , vol. 26, # 5 p. 633 - 638

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Citation Number: 79

Abstract

Results Synthesis. Two tripeptide specifiers, D-Val-Leu-Lys and D-Val-Leu-D-Lys, were synthesized in suitably protected forms as outlined in Scheme I. Boc-D-valine was condensed with leucine methyl ester by using N, N-dicyclohexylcarbodiimide (DCC) and 1- hydroxybenzotriazole (HOBT) 5 to give the dipeptide methyl ester 1 (91%), which gave the corresponding dipeptide acid, Boc-D-Val-Leu (3) after saponification (72%). An alternative ...