A Convenient Synthesis of Acyclic Adenosines with an Unsaturated Side Chain by Modification of 9-(2,3-O-Isopropylidene-D-Ribityl)Adenine
- 1 August 1998
- journal article
- research article
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 17 (8) , 1333-1345
- https://doi.org/10.1080/07328319808003472
Abstract
In expectation of discovering their antiviral activity, acyclic adenosine derivatives 7, 11, 12, and 16 were designed as analogs of neplanocin A (NPA) and L-eritadenine which are strong inhibitors of S-adenosyl-L-homocysteine hydrolase. The 1′,5′-seco-analog of 4′-deoxymethyl-NPA (DHCA) 7 was synthesized by dideoxygenation of 9-(2,3-O-isopropylidene-D-ribityl)adenine (2). Acyclic DHCA analogs 11 and 16 were obtained by Wittig reaction of the aldehyde 3 with Ph3P=CHCO2Et and Ph3P=CHCN, respectively. Hydrolysis of the ester 11 afforded a vinylog of L-eritadenine 12. The synthesized acyclic nucleosides 7, 10, and 11 were evaluated for antiviral activity, however, none of them showed any significant antiviral activity.This publication has 24 references indexed in Scilit:
- A Novel Approach for the Synthesis of Purine Acyclonucleosides Using 9-D-Ribitylpurines as a Chiral PoolSynlett, 1997
- S-Adenosyl-L-homocysteine hydrolase as a target for antiviral chemotherapyJournal of Medicinal Chemistry, 1991
- Controlled Synthesis of Enantio-, Regio-, and Diastereomers of Amino-4-pentenediols from 1,4-Pentadien-3-ol via Epoxy-4-pentenols I.erythro-1-Amino-4-pentene-2,3-diolsSynthesis, 1991
- 9-(Trans-2'-trans-3'-dihydroxycyclopent-4'-enyl) derivatives of adenine and 3-deazaadenine: potent inhibitors of bovine liver S-adenosylhomocysteine hydrolaseJournal of Medicinal Chemistry, 1988
- An efficient total synthesis of 3′-azido-3′-deoxythymidine (AZT) and 3′-azido-2′,3′-dideoxyuridine (AZDDU, CS-87) from D-mannitolTetrahedron Letters, 1988
- Mechanism of epimerization of 2,3-erythro-aldoses to 2,3-threo-Aldoses: An NMR studyMagnetic Resonance in Chemistry, 1985
- S-adenosyl-L-homocysteine hydrolase from mouse leukemic cells: Isolation and propertiesCollection of Czechoslovak Chemical Communications, 1983
- Synthesis and antiviral activity of stereoisomeric eritadeninesCollection of Czechoslovak Chemical Communications, 1982
- Eritadenines - Novel type of potent inhibitors of S-adenosyl-L-homocysteine hydrolaseCollection of Czechoslovak Chemical Communications, 1982
- Interconversions of hexofuranosyl nucleosides. I. Synthesis of 9-.beta.-L-gulofuranosyladenine from 9-.alpha.-D-mannofuranosyladenineThe Journal of Organic Chemistry, 1972