Convenient syntheses of 6-methylpurine and related nucleosides

被引:22
作者
Hassan, AEA [1 ]
Abou-Elkair, RAI [1 ]
Montgomery, JA [1 ]
Secrist, JA [1 ]
机构
[1] So Res Inst, Dept Organ Chem, Drug Discovery Div, Birmingham, AL 35255 USA
关键词
D O I
10.1080/15257770008035035
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Efficient methods for the synthesis of 6-methylpurine (3), 9-(2-deoxy-beta-D-erythro-pentofuranosyl)-6-methylpurine (8), and 6-methyl-9-beta-D-ribofuranosylpurine (5) are described. Methodology involving the (Ph3P)(4)Pd catalyzed cross-coupling reaction of CH3ZnBr with several different 6-chloropurine derivatives is described in high yield. This methodology now provides a facile and high-yielding synthesis of 8, which is needed in significant amounts for studies in cancer gene therapy.
引用
收藏
页码:1123 / 1134
页数:12
相关论文
共 32 条
[21]   In vivo gene therapy of cancer with E-coli purine nucleoside phosphorylase [J].
Parker, WB ;
King, SA ;
Allan, PW ;
Bennett, LL ;
Secrist, JA ;
Montgomery, JA ;
Gilberg, KS ;
Waud, WR ;
Wells, AH ;
Gillespie, GY ;
Sorscher, EJ .
HUMAN GENE THERAPY, 1997, 8 (14) :1637-1644
[22]  
PHILIPS FREDERICK S., 1954, ANN NEW YORK ACAD SCI, V60, P283
[23]   NUCLEIC-ACID RELATED COMPOUNDS .8. DIRECT CONVERSION OF 2'-DEOXYINOSINE TO 6-CHLOROPURINE 2'-DEOXYRIBOSIDE AND SELECTED 6-SUBSTITUTED DEOXYNUCLEOSIDES AND THEIR EVALUATION AS SUBSTRATES OF ADENOSINE DEAMINASE [J].
ROBINS, MJ ;
BASOM, GL .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1973, 51 (19) :3161-3169
[24]   PURINE NUCLEOSIDES .1. SYNTHESIS OF CERTAIN 6-SUBSTITUTED-9-(TETRAHYDRO-2-PYRANYL)-PURINES AS MODELS OF PURINE DEOXYNUCLEOSIDES [J].
ROBINS, RK ;
LEWIS, LR ;
TAYLOR, EC ;
GODEFROI, EF ;
JACKSON, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (11) :2574-&
[25]   Gene therapy of cancer:: Activation of nucleoside prodrugs with E-coli purine nucleoside phosphorylase [J].
Secrist, JA ;
Parker, WB ;
Allan, PW ;
Bennett, LL ;
Waud, WR ;
Truss, JW ;
Fowler, AT ;
Montgomery, JA ;
Ealick, SE ;
Wells, AH ;
Gillespie, GY ;
Gadi, VK ;
Sorscher, EJ .
NUCLEOSIDES & NUCLEOTIDES, 1999, 18 (4-5) :745-757
[26]   SYNTHESIS OF 6-SUBSTITUTED PURINE N-7-(2-DEOXY-BETA-D-RIBONUCLEOSIDES) VIA ANION GLYCOSYLATION AND ANOMERIZATION DURING THE N-7/N-9-GLYCOSYL TRANSFER [J].
SEELA, F ;
WINTER, H .
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1995, 14 (1-2) :129-142
[27]  
SORSCHER EJ, 1994, GENE THER, V1, P233
[28]   GENERAL METHOD FOR ALKYLATION AND ALKENYLATION OF HETEROCYCLES [J].
TAYLOR, EC ;
MARTIN, SF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (26) :8095-8102
[29]   ANTIVIRAL ACTIVITY OF C-ALKYLATED PURINE NUCLEOSIDES OBTAINED BY CROSS-COUPLING WITH TETRAALKYLTIN REAGENTS [J].
VANAERSCHOT, AA ;
MAMOS, P ;
WEYNS, NJ ;
IKEDA, S ;
DECLERCQ, E ;
HERDEWIJN, PA .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (20) :2938-2942
[30]   C-SUBSTITUTION OF NUCLEOSIDES WITH AID OF ESCHENMOSER SULFIDE CONTRACTION [J].
VORBRUGGEN, H ;
KROLIKIEWICZ, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (11) :689-690