Covalent Analogues of DNA Base-Pairs and Triplets VII. Synthesis and Cytostatic Activity of Bis(purin-6-yl)acetylene and -diacetylene Nucleosides

[img]PDF - Authorized users only
Language: English
141Kb
Title:Covalent Analogues of DNA Base-Pairs and Triplets VII. Synthesis and Cytostatic Activity of Bis(purin-6-yl)acetylene and -diacetylene Nucleosides
Creators:
Nauš, Petr
Votruba, Ivan
Hocek, Michal
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 10, pp. 1955-1970
Uncontrolled Keywords:Desilylation, Protecting groups, Purines, Nucleosides, Oxidative dimerization, Nucleobases, Cytostatics, Alkynes, Cross-coupling reactions, Base-pairs

Abstract

The title bis(purin-6-yl)acetylene and -diacetylene nucleoside derivatives were prepared as covalent base-pair analogues starting from acyl-protected 6-ethynylpurine and 6-iodopurine nucleosides by the Sonogashira cross-coupling or oxidative alkyne-dimerization reactions followed by deprotection. The key starting acyl-protected 6-ethynylpurine nucleosides were prepared by a sequence of cross-coupling reactions of protected 6-halopurine nucleosides with (trimethylsilyl)acetylene followed by a modified desilylation with TBAF in presence of acetic acid. Surprisingly, the acyl-protected nucleosides exhibited significant cytostatic activity higher than the fully deprotected title compounds. <p>

Title:Covalent Analogues of DNA Base-Pairs and Triplets VII. Synthesis and Cytostatic Activity of Bis(purin-6-yl)acetylene and -diacetylene Nucleosides
Creators:
Nauš, Petr
Votruba, Ivan
Hocek, Michal
Uncontrolled Keywords:Desilylation, Protecting groups, Purines, Nucleosides, Oxidative dimerization, Nucleobases, Cytostatics, Alkynes, Cross-coupling reactions, Base-pairs
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:69
Number:10
Page Range:pp. 1955-1970
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20041955UNSPECIFIED
ID Code:2314
Item Type:Article
Deposited On:06 Feb 2009 17:17
Last Modified:06 Feb 2009 16:17

Citation

Nauš, Petr; Votruba, Ivan; Hocek, Michal (2004) Covalent Analogues of DNA Base-Pairs and Triplets VII. Synthesis and Cytostatic Activity of Bis(purin-6-yl)acetylene and -diacetylene Nucleosides. Collection of Czechoslovak Chemical Communications, 69 (10). pp. 1955-1970. ISSN 0010-0765

Repository Staff Only: item control page