Synthesis of polymethylene chain-bridged 6-substituted 8-azapurines and related compounds

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Title:Synthesis of polymethylene chain-bridged 6-substituted 8-azapurines and related compounds
Creators:
Párkányi, Cyril
Yuan, Hui Liang
Marín-Montes, Martha C.
Essoussi, Hans T.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 11, pp. 2382-2388

Abstract

The synthesis of a series of polymethylene chain-bridged 8-azapurines as potential DNA intercalating agents is described. N,N’-Bis(5-amino-6-chloro-4-pyrimidyl)-1,3-diaminopropane (<i>III</i>), N,N”-bis(5-amino-6chloro-4-pyrimidyl)-1,8-diaminooctane (<i>IV</i>), and N,N’-bis(5-amino-6-chloro-4-pyrimidyl)-1,12-diaminododecane (<i>V</i>) were synthesized from 5-amino-4,6-dichloropyrimidine (<i>I</i>) and 1,3-diaminopropane (<i>II, n</i> = 3), 1,8-diaminooctane (<i>II, n</i> = 8), and 1,12-diaminododecane (<i>II, n</i> = 12), respectively, as the starting materials. 1,3-Bis(6-chloro-9-purinyl)propane (<i>VI</i>), 1,8-bis(6-chloro-9-purinyl)octane (<i>VII</i>), and 1,12-bis(6-chloro-9-purinyl)dodecane (<i>VIII</i>) were prepared by acid-catalyzed reaction of the corresponding pyrimidines <i>III-V</i> with triethyl orthoformate in N,N-dimethylacetamide. The polymethylene chain-bridged 6-hydroxy-8-azapurines <i>XII-XIV</i> were obtained via diazotization of the corresponding pyrimidines. The spectral data and other physical properties of the new compounds have been determined.

Title:Synthesis of polymethylene chain-bridged 6-substituted 8-azapurines and related compounds
Creators:
Párkányi, Cyril
Yuan, Hui Liang
Marín-Montes, Martha C.
Essoussi, Hans T.
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:56
Number:11
Page Range:pp. 2382-2388
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19912382UNSPECIFIED
ID Code:5167
Item Type:Article
Deposited On:22 Feb 2010 11:32
Last Modified:22 Feb 2010 10:32

Citation

Párkányi, Cyril; Yuan, Hui Liang; Marín-Montes, Martha C.; Essoussi, Hans T. (1991) Synthesis of polymethylene chain-bridged 6-substituted 8-azapurines and related compounds. Collection of Czechoslovak Chemical Communications, 56 (11). pp. 2382-2388. ISSN 0010-0765

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