Covalent analogues of DNA base-pairs and triplets. Part 2. Synthesis and cytostatic activity of bis(purin-6-yl) acetylenes, -diacetylenes and related compounds

被引:34
作者
Hocek, M [1 ]
Votruba, I [1 ]
机构
[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CZ-16610 Prague 6, Czech Republic
关键词
D O I
10.1016/S0960-894X(02)00077-X
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The title bis(purin-6-yl)acetylenes, -diacetylenes, -ethylenes and -ethanes were prepared as covalent base-pair analogues starting from 6-ethynylpurines and 6-iodopurines by cross-coupling and homo-coupling reactions and hydrogenations. The bis(purin-6-yl)acetylenes and -diacetylenes exhibited significant cytostatic activity in vitro (IC50=0.4-1.0 mumol/l). (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1055 / 1058
页数:4
相关论文
共 42 条
[1]   Tautomerization dynamics of a model base pair in DNA [J].
Abou-Zied, OK ;
Jimenez, R ;
Romesberg, FE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) :4613-4614
[2]   SYNTHESIS OF BRIDGED DINUCLEOSIDES [J].
AGATHOCLEOUS, DC ;
PAGE, PCB ;
COSSTICK, R ;
GALPIN, IJ ;
MCLENNAN, AG ;
PRESCOTT, M .
TETRAHEDRON, 1990, 46 (06) :2047-2058
[3]  
AKAHORI K, 1984, TETRAHEDRON LETT, V25, P2379, DOI 10.1016/S0040-4039(01)80260-4
[4]  
BAGULEY BC, 1991, ANTI-CANCER DRUG DES, V6, P1
[5]   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
[6]   Deoxyadenosine and thymidine bases held proximal and distal by means of a covalently-linked dimensional analogue of dA center dot dT: Intramolecular vs intermolecular hydrogen bonding [J].
Bhat, B ;
Leonard, NJ ;
Robinson, H ;
Wang, AHJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (44) :10744-10751
[7]   2'(3')-O-L-AMINOACYL DERIVATIVES OF BRIDGED ADENINE RIBONUCLEOSIDES AS SUBSTRATES FOR RIBOSOMAL PEPTIDYLTRANSFERASE [J].
BHUTA, P ;
LI, C ;
ZEMLICKA, J .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1977, 77 (04) :1237-1244
[8]   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
[9]   ISOLATION AND IDENTIFICATION OF CROSS-LINKS FROM FORMALDEHYDE-TREATED NUCLEIC-ACIDS [J].
CHAW, YFM ;
CRANE, LE ;
LANGE, P ;
SHAPIRO, R .
BIOCHEMISTRY, 1980, 19 (24) :5525-5531
[10]   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