Synthesis of 3′-C-branched 1′,5′-anhydromannitol nucleosides as new antiherpes agents

作者: Nafizal Hossain , Herman van Halbeek , Erik De Clercq , Piet Herdewijn

DOI: 10.1016/S0040-4020(97)10431-8

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摘要: Abstract A series of 3′-β-C-branched anhydromannitol nucleosides were conveniently synthesized starting from commercially available d -ribose. The reaction sequences were: (i) conversion the protected pentofuranose to corresponding nitrohexopyranose; (ii) addition conjugated base nitrosugar formaldehyde; (iii) removal nitro group by n-tributyltin hydride treatment and (iv) Mitsunobu type alkylation introduce nucleobase. conformation intermediates final compounds deduced NMR analysis. thymine congener showed potent activity against herpes simplex virus (HSV).

参考文章(27)
P. J. O'Hanlon, P. H. Bentley, Anti-infectives : recent advances in chemistry and structure-activity relationships Royal Society of Chemistry. ,(1997)
Roy Lester Whistler, Melville Lawrence Wolfrom, Derek H. Shaw, James N. BeMiller, Methods in Carbohydrate Chemistry ,(1965)
Katherine Stott, Jonathan Stonehouse, James Keeler, Tsang-Lin Hwang, A. J. Shaka, Excitation Sculpting in High-Resolution Nuclear Magnetic Resonance Spectroscopy: Application to Selective NOE Experiments Journal of the American Chemical Society. ,vol. 117, pp. 4199- 4200 ,(1995) , 10.1021/JA00119A048
Noboru Ono, Hideyoshi Miyake, Rui Tamura, Aritsune Kaji, A new synthetic method: Direct replacement of the nitro group by hydrogen or deuterium Tetrahedron Letters. ,vol. 22, pp. 1705- 1708 ,(1981) , 10.1016/S0040-4039(01)90417-4
María-Jesús Pérez-Pérez, Erik De Clercq, Piet Herdewijn, Synthesis and antiviral activity of 2-deoxy-1,5-anhydro-D-mannitol nucleosides containing a pyrimidine base moiety Bioorganic & Medicinal Chemistry Letters. ,vol. 6, pp. 1457- 1460 ,(1996) , 10.1016/S0960-894X(96)00244-2
Yuris Maurinsh, Jan Schraml, Hans De Winter, Norbert Blaton, Oswald Peeters, Eveline Lescrinier, Jef Rozenski, Arthur Van Aerschot, Erik De Clercq, Roger Busson, Piet Herdewijn, Synthesis and Conformational Study of 3-Hydroxy-4-(Hydroxymethyl)-1-Cyclohexanyl Purines and Pyrimidines. Journal of Organic Chemistry. ,vol. 62, pp. 2861- 2871 ,(1997) , 10.1021/JO962204X
U. Piantini, O. W. Sorensen, Richard R. Ernst, Multiple quantum filters for elucidating NMR coupling networks Journal of the American Chemical Society. ,vol. 104, pp. 6800- 6801 ,(1982) , 10.1021/JA00388A062