Stereoselective Synthesis of Some 3-Nitroglucopyranosyladenine Analogues via a Nitroolefin: Intermediate as Potential Therapeutic Agents

REFERENCES

• Fox , J. J. , Watanabe , K. A. and Bloch , A. 1966 . Progress in Nucleic Acid Research and Molecular Biology , Edited by: Davidson , J. N. and Cohn , W. E. p. 251 Academic Press .
   Google Scholar
• Venulet , J. and VanEtten , L. 1970 . The chemistry of the nitro and nitroso group Part 2 , Edited by: Feuer , H. p. 201 Interscience Publishers .
   Google Scholar
• Ohta , N. , Minamoto , K. , Yamamoto , T. , Koide , N. and Sakoda , S. 1996 . Nucleosides Nudeotides , 15 : 833 – 855 .
   Google Scholar
• In this context, the first synthesis of 3′-deoxy-3′-nitrothymidine and its 2′,3′-didehydro analogue as potential anti-AIDS substances has been recorded recently by Hossain et al.5
   Google Scholar
• Hossain , N , Papchikhin , A. , Garg , N. , Fedorov , L and Chattopadhyaya , J. Nucleosides Nudeotides , 12 499 – 528 .
   Google Scholar
• Hossain , N. , Garg , N. and Chattopadhyaya , J. 1993 . Tetrahedron , 49 : 10061 – 10068 .
   Web of Science ®Google Scholar
• Beranek , J. , Friedman , H. , Watanabe , K. A. and Fox , J. J. 1965 . J. Heterocycl. Chem. , 2 : 188 – 191 .
   Web of Science ®Google Scholar
• An attempt to isolate compound 6 as a hydrochloride salt has also failed.
   Google Scholar
• Biffin , M. E. C. , Miller , J. and Paul , D. B. 1971 . The chemistry of azido groupⁿ , Edited by: Patai , S. p. 57 Interscience Publishers .
   Google Scholar
• Yamamoto , T. , Tsuboike , K. and Minamoto , K. 1996 . Nucleic Acids Symp. Series , 35 : 35 – 36 .
   Google Scholar
• Similar azide reactions in THF or acetone revealed the formations of compound 11 and a similar amount of a far less polar product (silica gel TLC; CHCl3/EtOH, 9:1). The latter compound was isolated by column chromatography, recrystallized from MeOH at room temperature (mp 178–180°C) and shown to absorb at 2140 cm−1 (N3). However, repeated elemental analyses gave no satisfactory analysis values for this compound probably owing to thermal change to 11. In fact, its partial conversion into 11 was observed by TLC after being heated in MeOH for 30 min. Probably, the more electronegative adenine base would make H-3 more labile, thus rendering the azide insertion of the initially formed Michael adduct more facile. Polarity or basisity of the reaction medium may also influence the insertion. Elimination of nitrous acid from iv would occur rapidly to effect resonance stabilization.
   Google Scholar
• Huryn , D. M. and Okabe , M. 1992 . Chem. Rev. , 92 : 1745 – 1768 .
   Web of Science ®Google Scholar