136982-89-3Relevant academic research and scientific papers
2-Substituted-4-substituted-1,3-dioxolanes and use thereof
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Page column 51 -52, (2010/11/29)
Nucleoside analogues containing a 1,3-dioxolane structure are suitable antiviral agents, particulary for the treatment of the HIV infections in mammals, especially humans. Examples of the nucleoside analogues include: cis-2-acetoxymethyl-4-(thymin-1′-yl)-1,3,-dioxolane, cis-2-hydroxymethyl-4-(thymin-1′-yl)-1,3-dioxolane, cis-2-benzoyloxymethyl-4-(cytosin-1′-yl)-1,3-dioxolane, and cis-2-hydroxymethyl-4-(cytosin-1′-yl)-1,3-dioxolane. These compounds can be in the form of their racemates or their separate enantiomers.
Enantiomerically pure β-D-dioxolane-nucleosides
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, (2008/06/13)
A method and composition for the treatment of humans infected with HIV that includes the administration of an HIV treatment amount of an enantiomerically pure β-D-dioxolanyl purine nucleoside of the formula: STR1 wherein R is OH, Cl, NH2, or H,
Process for the preparation of enantiomerically pure β-D-(-)-dioxolane-nucleosides
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, (2008/06/13)
An asymmetric process for the preparation of enantiomerically pure β-D-(-)-dioxolane-nucleosides. The enantiomerically pure dioxolane nucleosides are active HIV agents, that are significantly more effective than the prior prepared racemic mixtures of the
Divergent Asymmetric Syntheses of Dioxolane Nucleoside Analogues
Evans, Colleen A.,Dixit, Dilip M.,Siddiqui, M. Arshad,Jin, Haolun,Tse, H. L. Allan,et al.
, p. 2319 - 2322 (2007/10/02)
Oxidative degradation of benzyloxymethylacetals derived from D-mannitol or L-ascorbic acid provides dioxolane intermediate 6 and 7 useful in the synthesis of all the stereoisomers of dioxolane nucleoside analogues.
Asymmetric Synthesis of 1,3-Dioxolane-Pyrimidine Nucleosides and Their Anti-HIV Activity
Kim, Hea O.,Ahn, Soon K.,Alves, Antonio J.,Beach, J. Warren,Jeong, Lak S.,et al
, p. 1987 - 1995 (2007/10/02)
In order to study the structure-activity relationships of dioxolane nucleosides as potential anti-HIV agents, various enantiomerically pure dioxolane-pyrimidine nucleosides have been synthesized and evaluated against HIV-1 in human peripheral blood mononuclear cells.The enantiomerically pure key intermediate 8 has been synthesized in nine steps from 1,6-anhydro-D-mannose (1), which was condensed with 5-substituted pyrimidines to obtain various dioxolane-pyrimidine nucleosides.Upon evaluation of these compounds, cytosine derivative 19 was found to exhibit the most potent anti-HIV agent although it is the most toxic.The order of anti-HIV potency was as follows: cytosine (β-isomer) > thymine > cytosine (α-isomer) > 5-chlorouracil > 5-bromouracil > 5-fluorouracil derivatives.Uracil, 5-methylcytosine, and 5-iodouracil derivatives were found to be inactive.Interestingly, α-isomer 20 showed good anti-HIV activity without cytotoxicity.As expected, other α-isomers did not exhibit any significant antiviral activity. (-)-Dioxolane-T was 5-fold less effective against AZT-resistant virus than AZT-sensitive virus.
Asymmetric synthesis of enantiomerically pure (-)-(1'R,4'R)-dioxolane-thymine and its anti-HIV activity
Chu,Ahn,Kim,Beach,Alves,Jeong,Islam,Van Roey,Schinazi
, p. 3791 - 3794 (2007/10/02)
An asymmetric synthesis leading to the enantiomerically pure dioxolane-T has been achieved and its crystal structure has been determined and compared to the previously reported racemate. (-)-(1'R,4'R)-dioxolane-T was found to have potent and selective ant
(±)-Dioxolane-T ((±)-1-[(2β,4β)-2-(hydroxymethyl)-4-dioxolanyl]thymine). A new 2',3'-dideoxynucleoside prototype with in vitro activity against HIV
Norbeck,Spanton,Broder,Mitsuya
, p. 6263 - 6266 (2007/10/02)
A novel analogue of 3'-deoxythymidine, in which the 3'-carbon is replaced by oxygen, was synthesized in 5 steps from benzyloxyacetaldehyde dimethyl acetal and (±)-methyl glycerate. In ATH8 cells, this analogue showed significant inhibition of the infectiv
