136982-89-3Relevant articles and documents
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.
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.