Synthesis ofCis-1-[(2-Hydroxymethyl) Cyclopentyl]Uridine and Determination of its Conformation by X-Ray Crystallography and Ami Theoretical Calculations
- 1 June 1996
- journal article
- research article
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 15 (6) , 1179-1187
- https://doi.org/10.1080/07328319608007386
Abstract
Abtract:The title compound 1 was prepared from racemic cis-2-hydroxymethylcyclo pentylamine, constructing the heterocyclic base in a two-step procedure (64 % yield). The crystal structure of the compound was determined and its conformation was studied using AMI theoretical calculations. The calculated low-energy conformations were similar to those reported for several other nucleoside analogues, and one of them closely corresponded to the X-ray structure.Keywords
This publication has 11 references indexed in Scilit:
- Synthesis and Antiviral Activity of 1,2-CarbonucleosidesNucleosides, Nucleotides and Nucleic Acids, 1995
- Conformation of 3-Substituted Purine Nucleoside Studied By X-Ray Crystallography and Theoretical CalculationsNucleosides and Nucleotides, 1994
- Solid-State and Solution Conformations of the Potent HIV Inhibitor, 4'-AzidothymidineJournal of Medicinal Chemistry, 1994
- Solid-state and solution conformation of 3'-amino-3'-deoxythymidine, precursor to a noncompetitive inhibitor of HIV-1 reverse transcriptaseJournal of Medicinal Chemistry, 1991
- Correlation between preferred sugar ring conformation and activity of nucleoside analogues against human immunodeficiency virus.Proceedings of the National Academy of Sciences, 1989
- The anti-conformation of 2′,3′-dideoxy nucleosides may be essential for anti-HIV activity: Evidence from the crystal structure of 2′,3′-dideoxy formycin ABiochemical and Biophysical Research Communications, 1989
- Regiospecific synthesis of cyclopentane analogs of (2′- and 3′-deoxy-threo-pentofuranosyl)-uracil and -2-thiouracil nucleosidesCanadian Journal of Chemistry, 1985
- Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular modelJournal of the American Chemical Society, 1985
- Synthesis of the carbocyclic analogs of uracil nucleosidesJournal of Heterocyclic Chemistry, 1976
- 2‐Azabicyclo [3.2.0] Heptane‐3‐OneIsrael Journal of Chemistry, 1972