Synthesis of 6-substituted 1-deazapurine 2'-deoxyribonucleosides

被引:12
作者
Wenzel, T [1 ]
Seela, F [1 ]
机构
[1] UNIV OSNABRUCK,INST CHEM,ORGAN & BIOORGAN CHEM LAB,D-49069 OSNABRUCK,GERMANY
关键词
D O I
10.1002/hlca.19960790117
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis of 6-substituted 1-deazapurine 2'-deoxyribonucleosides is described. Glycosylation of the 1-deazapurine (imidazo[4,5-b]pyridine) anions with the alpha-D-halogenose 5 gives stereoselectively N-7- and N-9-regioisomers. H-1-NMR NOE and C-13-NMR spectroscopy are used for unambiguous assignment of isomers, and N-15-NMR chemical shifts are correlated with sigma(para) Hammett constants and point charges.
引用
收藏
页码:169 / 178
页数:10
相关论文
共 26 条
[1]   DEAZA ANALOGS OF ADENOSINE AS INHIBITORS OF BLOOD-PLATELET AGGREGATION [J].
ANTONINI, I ;
CRISTALLI, G ;
FRANCHETTI, P ;
GRIFANTINI, M ;
MARTELLI, S ;
PETRELLI, F .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1984, 73 (03) :366-369
[2]   THE STEREOSELECTIVE ENZYMATIC-SYNTHESIS OF 9-BETA-D-2'-DEOXYRIBOFURANOSYL 1-DEAZAPURINE [J].
BETBEDER, D ;
HUTCHINSON, DW ;
RICHARDS, AO .
NUCLEIC ACIDS RESEARCH, 1989, 17 (11) :4217-4222
[3]  
CHATTERJEE S. K., 1960, JOUR SCI AND INDUST RES [INDIA], V19, P35
[4]   PURINE AND 1-DEAZAPURINE RIBONUCLEOSIDES AND DEOXYRIBONUCLEOSIDES - SYNTHESIS AND BIOLOGICAL-ACTIVITY [J].
CRISTALLI, G ;
VITTORI, S ;
ELEUTERI, A ;
GRIFANTINI, M ;
VOLPINI, R ;
LUPIDI, G ;
CAPOLONGO, L ;
PESENTI, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (07) :2226-2230
[5]   IMPROVED SYNTHESIS AND ANTITUMOR-ACTIVITY OF 1-DEAZAADENOSINE [J].
CRISTALLI, G ;
FRANCHETTI, P ;
GRIFANTINI, M ;
VITTORI, S ;
BORDONI, T ;
GERONI, C .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (09) :1686-1688
[6]   GLYCOSYLATION REACTIONS OF 6-NITRO-1,3-DIDEAZAPURINE AND 6-NITRO-1-DEAZAPURINE [J].
DEVLIN, TA ;
LACROSAZROUANET, E ;
VO, D ;
JEBARATNAM, DJ .
TETRAHEDRON LETTERS, 1995, 36 (10) :1601-1604
[7]   PREDICTION OF PROTON MAGNETIC-RESONANCE SHIFTS - THE DEPENDENCE ON HYDROGEN CHARGES OBTAINED BY ITERATIVE PARTIAL EQUALIZATION OF ORBITAL ELECTRONEGATIVITY [J].
GASTEIGER, J ;
MARSILI, M .
ORGANIC MAGNETIC RESONANCE, 1981, 15 (04) :353-360
[8]   ITERATIVE PARTIAL EQUALIZATION OF ORBITAL ELECTRONEGATIVITY - A RAPID ACCESS TO ATOMIC CHARGES [J].
GASTEIGER, J ;
MARSILI, M .
TETRAHEDRON, 1980, 36 (22) :3219-3228
[9]   ALPHA-THYMIDIN [J].
HOFFER, M .
CHEMISCHE BERICHTE-RECUEIL, 1960, 93 (12) :2777-2781
[10]  
IKEHARA M, 1974, J BIOCHEM-TOKYO, V76, P107, DOI 10.1093/oxfordjournals.jbchem.a130534