Analogues of the antiviral acyclonucleoside 9-(4-hydroxy-3-hydroxymethylbutyl)guanine. Part 3. Modification of a 3′-hydroxymethyl group
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 2777-2784
- https://doi.org/10.1039/p19880002777
Abstract
Syntheses of 3′-hydroxymethyl modified analogues of the potent antiviral agent 9-(4-hydroxy-3-hydroxymethylbutyl)guanine (1c) are described. These include methyl homologues (7a, b), chain-extended compounds such as the methylene homologue (16) and hydroxyalkyl ethers (26b, c), and methoxy (26a), bromo (28), azido (29), amino (30), and formamido (31) substituted analogues. Compounds (7a, b), (16), and (26a–c) were prepared by construction of an appropriately functionalised alkyl unit followed by purine alkylation and deprotection, whereas compounds (28)–(31) were prepared by selective modification of (1c). The formamido analogue (31) showed moderate anti-herpes virus activity and compounds (16), (26b), and (29) weak activity.This publication has 10 references indexed in Scilit:
- Analogues of the antiviral acyclonucleoside 9-(4-hydroxy-3-hydroxymethylbutyl)guanine. Part 2. Substitutions on C-1? and C-3? of the acyclic N-9 substituentJournal of the Chemical Society, Perkin Transactions 1, 1988
- Analogues of the antiviral acyclonucleoside 9-(4-hydroxy-3-hydroxymethylbutyl)guanine. Part 1. Substitutions on C-2? of the acyclic N-9 substituentJournal of the Chemical Society, Perkin Transactions 1, 1988
- Synthesis and antiviral activity of 9-[4-hydroxy-3-(hydroxymethyl)but-1-yl]purinesJournal of Medicinal Chemistry, 1987
- Antiherpesvirus activity of 9-(4-hydroxy-3-hydroxy-methylbut-1-yl)guanine (BRL 39123) in cell cultureAntimicrobial Agents and Chemotherapy, 1987
- Mode of action, toxicity, pharmacokinetics, and efficacy of some new antiherpesvirus guanosine analogs related to buciclovirAntimicrobial Agents and Chemotherapy, 1986
- Metabolism and mode of action of (R)-9-(3,4-dihydroxybutyl)guanine in herpes simplex virus-infected vero cells.Journal of Biological Chemistry, 1986
- Antiherpes effects and pharmacokinetic properties of 9-(4-hydroxybutyl) guanine and the (R) and (S) enantiomers of 9-(3,4-dihydroxybutyl)guanineAntimicrobial Agents and Chemotherapy, 1985
- Antiherpes Simplex Virus Activity of 9-[4-Hydroxy-3-(hydroxymethyl)-1-butyl] guanineNucleosides, Nucleotides and Nucleic Acids, 1984
- Antiherpetic activity and mechanism of action of 9-(4-hydroxybutyl)guanineAntiviral Research, 1983
- 9-(3,4-dihydroxybutyl)guanine, a new inhibitor of herpesvirus multiplicationAntimicrobial Agents and Chemotherapy, 1983