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Institute of Organic Chemistry & Biochemistry, Collection of Czechoslovak Chemical Communications, 10(67), p. 1560-1578, 2002

DOI: 10.1135/cccc20021560

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Covalent Analogues of DNA Base-Pairs and Triplets V. Synthesis of Purine-Purine and Purine-Pyrimidine Conjugates Connected by Diverse Types of Acyclic Carbon Linkages

Journal article published in 2002 by Michal Hocek ORCID, Hana Dvořáková, Ivana Císařová
This paper is available in a repository.
This paper is available in a repository.

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Abstract

The title 1,2-bis(purin-6-yl)acetylenes, -diacetylenes, -ethylenes and -ethanes were prepared as covalent base-pair analogues starting from 6-ethynylpurines and 6-iodopurines by the Sonogashira cross-coupling or oxidative alkyne-dimerization reactions followed by hydrogenations. 6-[(1,3-Dimethyluracil-5-yl)ethynyl]purine ( 11 ) was prepared analogously and hydrogenated to the corresponding purine-pyrimidine conjugates linked via vinylene and ethylene linkers. Unlike the cytostatic bis(purin-6-yl)acetylenes and -diacetylenes, the purine-pyrimidine conjugates were inactive. Crystal structures of bis(purin-6-yl)acetylene 6a , -diacetylene 8a and -ethane 5a were determined by single-crystal X-ray diffraction.