Synthesis and Biological Evaluation of Acyclic Neplanocin Analogues

Mei Hua, Phillip M. Korkowski, Robert Vince

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

Acyclic neplanocin analogues were prepared by condensation of adenine or N2-acetylguanine with (E)-l,4-dichlorobut-2-ene and subsequent hydrolysis. The N-9-substituted product 9- [E)-4-hydroxybut-2-enyl]adenine (5) was obtained when adenine was employed as the starting purine, while N2-acetylguanine yielded both the N-7 and N-9 isomers. Cell-culture studies revealed that only the chloro-substituted intermediate 9-[E)-4-chlorobut-2-enyl]adenine (4) exhibited significant cytotoxicity against P-388 mouse lymphoid leukemia cells, while the N-9-substituted guanine analogue 9-[E)-4-hydroxybut-2-enyl]guanine (10) inhibited replication of herpes simplex viruses type 1 and type 2.

Original languageEnglish (US)
Pages (from-to)198-200
Number of pages3
JournalJournal of medicinal chemistry
Volume30
Issue number1
DOIs
StatePublished - Jan 1 1987

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