Racemic Synthesis and Antiviral Evaluation of 4′(α)-Hydroxymethyl and 6′(α)-Methyl Substituted Apiosyl Nucleosides

REFERENCES

• De , Clercq, E. 1999 . Perspectives for the treatment of hepatitis B Virus infection . Int. J. Antimicrob. Agents , 112 : 81 – 95 . (a) (b) De Clercq, E. New anti-HIV agents and targets. Med. Res. Rev. 2002, 22, 531– 565
   Google Scholar
• Waga , T. , Nishizaki , T. , Miyakawa , I. , Ohrui , H. and Meguro , H. 1993 . Synthesis of 4′-C-methylnucleosides . Biosci. Biotech. Biochem. , 57 : 1433 – 1438 . (b) Walton, E.; Jenkins, S.R.; Nutt, R.F.; Holly, F.W. Synthesis and antiviral properties of several branched-chain sugar nucleosides. J. Med. Chem. 1969, 12, 306–309; (c) Matsuda, A.; Takenuki, K.; Sasaki, T.; Ueda, T. Radical deoxygenation of tert-alcohols in 1-(2-C-alkylpentofuranosyl)pyrimidines: Synthesis of (2′S)-2′-deoxy-2′-methylcytidine, an antileukemic nucleoside. J. Med. Chem. 1991, 34, 234–239.
   PubMed Web of Science ®Google Scholar
• O-Yang , C. , Wu , H.Y. , Fraser-Smith , E.B. and Walker , K.A.M. 1992 . Synthesis of 4′-cyanothymidine and analogs as potent inhibitors of HIV . Tetrahedron Lett , 33 : 37 – 40 .
   Web of Science ®Google Scholar
• Nair , V. and Tahnke , T. 1995 . Antiviral activities of isomeric dideoxynucleosides of D- and L-related stereochemistry . Antimicrob. Agents Chemother. , 39 : 1017 – 1029 .
   PubMed Web of Science ®Google Scholar
• Vair , V. , Wentel , T. , Chao , Q. and Jahnke , T.S. 1997 . Synthesis, enzymology, and anti-HIV studies of analogues of isodide oxyadenosine and its phosphorylated derivatives . Antiviral Res. , 34 : A55
   Google Scholar
• Sell , T.B. and Nair , V. 1993 . Synthetic approaches to novel isomeric dideoxynucleosides containing a chiral furanethanol carbohydrate moiety . Tetrahedron Lett. , 34 : 3527 – 3530 .
   Web of Science ®Google Scholar
• Katagiri , N. , Shiraishi , T. , Sato , H. , Toyota , A. , Kaneko , C. , Oh-hara , T. and Tsuruo , T. 1992 . Resolution of 9-(c-4,t-5-bishydroxymethylcyclopent-2-en-r-1-yl)-9 H-adenine and selective inhibition of human immunodeficiency virus by the (−) enantiomer . Biochem. Biophys. Res. Commun. , 184 : 154 – 159 . (b) Katagiri, N.; Nomura, M.; Sato, H.; Kaneko, C.; Yusa, K.; Tsuruo, T. Synthesis and anti-HIV activity of 9-[c-4,t-bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9 H-adenine. J. Med. Chem. 1992, 35, 1882– 1886.
   PubMed Web of Science ®Google Scholar
• Tanaka , M. , Norimine , Y. , Fujita , T. , Suemune , H. and Sakai , K. 1996 . Chemoenzymatic synthesis of antiviral carbocyclic nucleosides: asymmetric hydrolysis of meso-3,5-bis(acetoxymethyl)cyclopentenes using Rhizopus delemar Lipase . J. Org. Chem. , 61 : 6952 – 6957 .
   PubMed Web of Science ®Google Scholar
• Kim , J.W. , Choi , B.G. and Hong , J.H. 2004 . Stereoselective synthesis and antiviral activity of novel 4′(α)-hydroxymethyl and 6′(α)-methyl dually branched carbocyclic nucleosides . Bull. Korean Chem. Soc. , 25 : 1812 – 1816 .
   Web of Science ®Google Scholar