Collect. Czech. Chem. Commun. 2002, 67, 1560-1578

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

Michal Hoceka,*, Hana Dvořákováb and Ivana Císařovác

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, CZ-166 10 Prague 6, Czech Republic
b Laboratory of NMR Spectroscopy, Institute of Chemical Technology, Prague, Technická 5, CZ-166 28 Prague 6, Czech Republic
c Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 8, CZ-128 43 Prague 2, Czech Republic


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.

Keywords: Purines; Pyrimidines; Nucleobases; Alkynes; Cross-coupling reactions; Nucleosides; Sonogashira reaction; Hydrogen bonds.

References: 52 live references.