title: Synthesis of novel peptidyl adenosine antibiotic analogs.
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.
authors.affiliation: a Southern Research Institute, Drug Discovery Division , Birmingham , AL 35205 , USA.
authors.forename: Omar
authors.initials: O
authors.lastname: Moukha-Chafiq
authors.forename: Robert C
authors.initials: RC
authors.lastname: Reynolds
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000962:Antimalarials / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D006801:Humans; D015394:Molecular Structure; D021261:Parasitic Sensitivity Tests
chemical_list: D000962:Antimalarials; D000970:Antineoplastic Agents; D000241:Adenosine