Novel Carbocyclic Nucleosides Containing a Cyclobutyl Ring: Adenosine Analogues

(1S,1'R)-cis-1-(3'-aminomethyl-2',2'-dimethylcyclobutyl)ethanol (1) and (1S,1'R)-cis-1-[3'-(2-aminoethyl)-2',2'-dimethylcyclobutyl]ethanol (2) were used as precursors in the synthesis of cyclobutyl nucleoside analogues containing adenine and 8-azaadenine moiet...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 2001, Vol.49(9), pp.1174-1177
Hauptverfasser:	HERGUETA, Antonio R., FERNÁNDEZ, Franco, LÓPEZ, Carmen, BALZARINI, Jan, CLERCQ, Eric DE
Format:	Artikel
Sprache:	eng
Schlagworte:	Adenosine - analogs & derivatives Adenosine - chemistry Adenosine - pharmacology adenosine analogue Antibiotics. Antiinfectious agents. Antiparasitic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology antitumoral antiviral Antiviral agents Antiviral Agents - chemical synthesis Antiviral Agents - pharmacology Biological and medical sciences carbocyclic nucleoside Cyclobutanes - chemistry Ethanol - analogs & derivatives Ethanol - chemistry HeLa Cells Humans Indicators and Reagents Medical sciences Nucleosides - chemistry Nucleosides - pharmacology Pharmacology. Drug treatments respiratory syncytial virus Respiratory Syncytial Virus, Human - drug effects Tumor Cells, Cultured vaccinia virus Vaccinia virus - drug effects
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Zusammenfassung:	(1S,1'R)-cis-1-(3'-aminomethyl-2',2'-dimethylcyclobutyl)ethanol (1) and (1S,1'R)-cis-1-[3'-(2-aminoethyl)-2',2'-dimethylcyclobutyl]ethanol (2) were used as precursors in the synthesis of cyclobutyl nucleoside analogues containing adenine and 8-azaadenine moieties, which were tested as antiviral and antitumoral agents in a variety of assay systems. Compounds 8 and 9 displayed significant activity against respiratory syncytial virus, and compounds 14 and 15 were moderately active against vaccinia virus.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.49.1174