Cytostatic 6-arylpurine nucleosides III.: Synthesis and structure-activity relationship study in cytostatic activity of 6-aryl-, 6-hetaryl- and 6-benzylpurine ribonucleosides

被引:122
作者
Hocek, M [1 ]
Holy, A
Votruba, I
Dvorákova, H
机构
[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CZ-16610 Prague 6, Czech Republic
[2] Inst Chem Technol, Lab NMR Spect, CZ-16628 Prague, Czech Republic
关键词
purines; nucleosides; cross-coupling reactions; antineoplastic agents; antitumor activity; arylboronic acids; stannanes; organozinc reagents; Suzuki reaction;
D O I
10.1135/cccc20010483
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of fifteen 6-aryl-, 6-hetaryl- and 6-benzylpurine ribonucleosides has been prepared by Pd-catalyzed cross-coupling reactions of 6-chloro-9-(2,3,5-tri-O-acetyl-beta -D-ribofuranosyl)-purine with arylboronic acids, hetarylzinc halides, hetarylstannanes or benzylzinc halides followed by deprotection. Structure-activity relationship study revealed that besides 6-(4-substituted phenyl)purine nucleosides, also some 6-hetaryl- and 6-benzylpurine ribonucleosides possess considerable cytostatic activity.
引用
收藏
页码:483 / 499
页数:17
相关论文
共 22 条
[1]   9-benzylpurines with inhibitory activity against Mycobacterium tuberculosis [J].
Bakkestuen, AK ;
Gundersen, LL ;
Langli, G ;
Liu, FS ;
Nolsoe, JMJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (11) :1207-1210
[2]   Synthesis of 6-alkenyl- and 6-alkynylpurines with cytokinin activity [J].
Bråthe, A ;
Gundersen, LL ;
Rise, E ;
Eriksen, AB ;
Vollsnes, AV ;
Wang, LN .
TETRAHEDRON, 1999, 55 (01) :211-228
[3]   AN UNAMBIGUOUS SYNTHESIS OF ADENYLOSUCCINIC ACID AND ITS CONSTITUENT NUCLEOSIDE [J].
BUCK, IM ;
REESE, CB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :2937-2942
[4]   Synthesis of acyclic nucleotide analogues derived from 2-amino-6-C-substituted purines via cross-coupling reactions of 2-amino-9-{2-[(diisopropoxyphosphoryl)methoxy]ethyl}-6-halopurines with diverse organometallic reagents [J].
Cesnek, M ;
Hocek, M ;
Holy, A .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2000, 65 (08) :1357-1373
[5]   Use of the Suzuki reaction for the synthesis of aryl-substituted heterocycles as corticotropin-releasing hormone (CRH) antagonists [J].
Cocuzza, AJ ;
Chidester, DR ;
Culp, S ;
Fitzgerald, L ;
Gilligan, P .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (07) :1063-1066
[6]   6-CHLOROPURINES AND ORGANOSTANNANES IN PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS [J].
GUNDERSEN, LL .
TETRAHEDRON LETTERS, 1994, 35 (19) :3155-3158
[7]   6-HALOPURINES IN PALLADIUM-CATALYZED COUPLING WITH ORGANOTIN AND ORGANOZINC REAGENTS [J].
GUNDERSEN, LL ;
BAKKESTUEN, AK ;
AASEN, AJ ;
OVERAS, H ;
RISE, F .
TETRAHEDRON, 1994, 50 (32) :9743-9756
[8]   Convenient syntheses of 6-methylpurine and related nucleosides [J].
Hassan, AEA ;
Abou-Elkair, RAI ;
Montgomery, JA ;
Secrist, JA .
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2000, 19 (07) :1123-1134
[9]  
Havelková M, 1999, SYNLETT, P1145
[10]   Synthesis and cytostatic activity of substituted 6-phenylpurine bases and nucleosides:: Application of the Suzuki-Miyaura cross-coupling reactions of 6-chloropurine derivatives with phenylboronic acids [J].
Hocek, M ;
Holy, A ;
Votruba, I ;
Dvoráková, H .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (09) :1817-1825