Synthesis of novel Peptidyl adenosine antibiotic analogs

Academic Article

Abstract

  • A small library of peptidyl adenosine antibiotic analogs was synthesized, under the Pilot Scale Library Program of the NIH Roadmap initiative, from 2′,3′-O-isoproylideneadenosine-5′-carboxylic acid 2 in excellent yield. The coupling of the amino terminus of L-2-aminophenylbutyric methyl ester to a free 5′-carboxylic acid moiety of 2 followed by sodium hydroxide treatment led to carboxylic acid analog 4. Hydrolysis of this latter gave unprotected nucleoside analog 5. Intermediate 4 served as the precursor for the preparation of novel peptidyl adenosine analogs 6-18 in good yields and high purity through peptide coupling reactions to diverse amine derivatives. No marked anticancer and antimalaria activity was noted on preliminary cellular testing; however these analogs should be useful candidates for other types of biological activity. © 2014 Copyright © Taylor and Francis Group, LLC.
  • Digital Object Identifier (doi)

    Author List

  • Moukha-Chafiq O; Reynolds RC
  • Start Page

  • 53
  • End Page

  • 63
  • Volume

  • 33
  • Issue

  • 2