136884-16-7Relevant articles and documents
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,
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