d- andl-2‘,3‘-Didehydro-2‘,3‘-dideoxy-3‘-fluoro-carbocyclic Nucleosides: Synthesis, Anti-HIV Activity and Mechanism of Resistance
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چکیده
منابع مشابه
5'-Nor carbocyclic 5'-deoxy-5'-(isobutylthio)adenosine and a 2',3'-dideoxy-2',3'-didehydro derivative.
The inhibition of biochemical processes requiring S-adenosylmethionine as a co-factor have led to many nucleoside-based medicinal agents. Included in this group are 5'-deoxy-5'-(isobutylthio)adenosine (SIBA), a nucleoside with antiparasitic, antiviral and antiproliferative effects, and 5'-noraristeromycin, a carbocyclic-derived nucleoside with potent antiviral properties. This report brings tog...
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A series of 2',3'-dideoxy-2',2'-difluoro-4'-azanucleosides of both pyrimidine and purine nucleobases were synthesized in an efficient manner starting from commercially available L-pyroglutamic acid via glycosylation of difluorinated pyrrolidine derivative 15. Several 4'-azanucleosides were prepared as a separable mixture of α- and β-anomers. The 6-chloropurine analogue was obtained as a mixture...
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The discovery of a novel cytosine nucleoside, â-D-2′,3′-didehydro-2′,3′-dideoxy-5-fluorocytidine (D-D4FC), as a potent antihuman immunodeficiency virus (HIV) agent led us to synthesize a series of analogues and derivatives of â-D-D4FC that could be more selective and also possess increased glycosidic bond stability. The synthesized D-D4FC analogues were evaluated for antiHIV-1 activity, antican...
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Carbocyclic nucleoside analogues remain interesting target molecules having the potential to combine biological activity with greater metabolic stability than their sugar counterparts. This paper describes a rapid and versatile synthetic approach to such compounds based on commercial cyclopentenones (e.g., 1) that has been developed in our laboratory. Carbocyclic nucleosides like 2 0-methylaris...
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23-Amino-4',23-dideoxymycaminosyl tylonolide diethyl acetal (5) has been prepared from 4',23-dideoxy-23-iodomycaminosyl tylonolide diethyl acetal (3) by treatment with sodium azide followed by selective reduction of the resulting azide (4). 23-Acylamino-23-deoxy (6 approximately 8) and 23-deoxy-23-urethane-type compounds (12 approximately 15) were further prepared. Treatment of the 23-alkylamin...
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ژورنال
عنوان ژورنال: Journal of Medicinal Chemistry
سال: 2007
ISSN: 0022-2623,1520-4804
DOI: 10.1021/jm061304k