Synthesis and biological evaluation of acyclic neplanocin analogs
- 1 January 1987
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 30 (1), 198-200
- https://doi.org/10.1021/jm00384a033
Abstract
Acyclic neplanocin analogues were prepared by condensation of adenine or N2-acetylguanine with (E)-1,4-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.This publication has 8 references indexed in Scilit:
- Neplanocin A. A potent inhibitor of S-adenosylhomocysteine hydrolase and of vaccinia virus multiplication in mouse L929 cells.Journal of Biological Chemistry, 1984
- Synthesis of Purine and Pyrimidine TrihydroxyacyclonucleosidesNucleosides, Nucleotides and Nucleic Acids, 1984
- Biologically active acyclonucleoside analogues. II. The synthesis of 9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]guanine (BIOLF-62)Canadian Journal of Chemistry, 1982
- Studies on neplanocin A,new antitumor antibiotic. II. Structure determination.The Journal of Antibiotics, 1981
- Carbocyclic Analogs of Arabinosylpurine NucleosidesJournal of Pharmaceutical Sciences, 1980
- 9-(2-Hydroxyethoxymethyl)guanine activity against viruses of the herpes groupNature, 1978
- Selectivity of action of an antiherpetic agent, 9-(2-hydroxyethoxymethyl)guanineProceedings of the National Academy of Sciences, 1977
- SEARCHING FOR ANTIVIRAL MATERIALS FROM MICROBIAL FERMENTATIONSAnnals of the New York Academy of Sciences, 1965