Novel isomeric dideoxynucleosides as potential antiviral agents

Bolon, Pascal J.; Sells, Todd B.; Nuesca, Zoraida M.; Purdy, David F.; Nair, Vasu

doi:10.1016/s0040-4020(01)85259-5

Cited by 62 publications

(16 citation statements)

References 28 publications

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“…The syntheses of enantiomerically pure (S,S)-isodideoxyadenosine and (S,S)-isodideoxyinosine from D-xylose have been reported previously by Nair and coworkers (4,30). [ 6 Ci/mmol) was prepared from IsoddA by Moravek Biochemicals (Brea, Calif.).…”

Section: Methodsmentioning

confidence: 99%

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Antiviral, metabolic, and pharmacokinetic properties of the isomeric dideoxynucleoside 4(S)-(6-amino-9H-purin-9-yl)tetrahydro-2(S)-furanmethanol

Nair

Clair

Reardon

et al. 1995

Antimicrob Agents Chemother

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4(S)-(6-Amino-9H-purin-9-yl)tetrahydro-2(S)-furanmethanol ((subclone P5A) cell lines but were 12 and 11 M for human granulocyte-macrophage (CFU-GM) and erythroid (BFU-E) progenitor cells, respectively. When given orally to rats and mice, the compound was very well absorbed and rapidly eliminated. However, there was no detectable brain penetration by IsoddA in rats. Catabolic metabolites were not detected, and this is consistent with the observed resistance of the compound to metabolic degradation by adenosine deaminase.

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Section: Methodsmentioning

confidence: 99%

“…1). The synthesis of this compound has been reported by us, and its absolute stereochemistry has been established by X-ray crystallography (4,30). The enantiomer of this compound has been synthesized and discussed elsewhere (18).…”

mentioning

confidence: 99%

Antiviral, metabolic, and pharmacokinetic properties of the isomeric dideoxynucleoside 4(S)-(6-amino-9H-purin-9-yl)tetrahydro-2(S)-furanmethanol

Nair

Clair

Reardon

et al. 1995

Antimicrob Agents Chemother

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“…To shed some more light on the hybridization properties and the conformational requirement for duplex formation, oligonucleotides built up from structurally different isonucleosides were investigated. For this purpose, the enantiomeric anhydro-d-arabinitol 2 ([a] 20 D À 16.7 (c 0.647, MeOH ) was synthesized from l-xylose on an analogous synthetic route [16] [17]. For the synthesis of oligonucleotides consisting of the isonucleosides 1 and 2, the latter were transformed into the building blocks 5 and 7 by dimethoxyltritylation ( 3 4 and 6, respectively) and subsequent phosphitylation with 2-cyanoethyl diisopropylphosphoramidochloridite by the standard protocol ( Scheme 1).…”

mentioning

confidence: 99%

Synthesis and Duplex Stabilization of Oligonucleotides Consisting of Isonucleosides

Yang

Zhang

Min

et al. 1999

HCA

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“…The characteristic feature of these interesting compounds is the transposition of the nucleobase from its "classical" position 1 0 of the tetrahydrofurylmethanol to the neighboring 2 0 position. According to the published data [53,54], the major activity is expressed toward HIV. Interestingly, the activity is not limited to the standard stereochemistry, but active compounds are encountered in both series.…”

Section: Homentioning

confidence: 99%

“…There was a report in the literature about the N4-amidine derivative of HPMPC (54) that is easy to prepare by treatment of HPMPC with dimethylformamide dimethyl acetal and that would generate the parent drug by chemical hydrolysis [99]; also, there appeared a note about the activity of the 5-fluoro-HPMPC (55) [100]. …”

Section: 6-aza-(s)-chpmpcmentioning

confidence: 99%

Anti‐DNAVirus Agents

Holý

Clercq

2010

Burger's Medicinal Chemistry and Drug Discovery

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Anti‐DNA virus agents that are inhibitory to the replication of DNA viruses have been reviewed by Tim Middleton and Rockway in Burger's Medicinal Chemistry, 6th ed., volume 5. Here we will address the various agents effective against these different viruses. For each of the (classes of) compound(s), we will, where applicable, specifically focus on (i) the antiviral compounds that are clinically available; (ii) the antiviral compounds that are under (pre)clinical development; (iii) the mechanism of action of the compounds; (iv) their structure–activity relationship (SAR); (v) resistance that may have arisen; (vi) recent clinical data obtained with the compounds while under development. Previous reviews on antiviral agents have been dealing with “looking back in 2009 at the dawning of antiviral therapy now 50 years ago: an historical perspective,” highlighting the discovery of acyclovir [9‐(2‐hydroxyethoxymethyl)guanine] as a specific antiherpetic agent, “the design of drugs for HIV and HCV,” “HIV drug development: the next 25 years,” “interferons at age 50: past, current, and future impact on biomedicine,” “the way forward in HCV treatment‐finding the right path,” “antiviral treatment of chronic hepatitis B virus infections: the past, the present, and the future,” “antiviral agents active against influenza A viruses,” “the war against influenza: discovery and development of sialidase inhibitors,” “antivirals and antiviral strategies,” and “clinical potential of the acyclic nucleoside phosphonates cidofovir, adefovir, and tenofovir in treatment of DNA virus and retrovirus infections.”

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Novel isomeric dideoxynucleosides as potential antiviral agents

Cited by 62 publications

References 28 publications

Antiviral, metabolic, and pharmacokinetic properties of the isomeric dideoxynucleoside 4(S)-(6-amino-9H-purin-9-yl)tetrahydro-2(S)-furanmethanol

Antiviral, metabolic, and pharmacokinetic properties of the isomeric dideoxynucleoside 4(S)-(6-amino-9H-purin-9-yl)tetrahydro-2(S)-furanmethanol

Synthesis and Duplex Stabilization of Oligonucleotides Consisting of Isonucleosides

Anti‐DNAVirus Agents

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