Synthesis and Properties of 2-Guanidinopurines

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Title:Synthesis and Properties of 2-Guanidinopurines
Creators:
Česnek, Michal
Masojídková, Milena
Holý, Antonín
Šolínová, Veronika
Koval, Dušan
Kašička, Václav
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 71, 9, pp. 1303-1319
Uncontrolled Keywords:Acyclic nucleoside phosphonates, Electrophoresis, PMEDAP analogues, Purines, Nucleosides, Guanidines, Basicity, Dissociation constants

Abstract

2-Guanidinopurines were prepared as derivatives of 2,6-diamino-9-[2-(phosphonomethoxy)ethyl]-9<i>H</i>-purine (PMEDAP) (<strong>1</strong>), which shows an important antiviral activity. It completes earlier described synthesis of 6-guanidinopurine derivatives. The title compounds were obtained by the reaction of the corresponding 2-chloropurines with guanidine. 2- And 6-guanidinopurines were used as model compounds for determination of dissociation constants (p<i>K</i><sub>a</sub>) of their ionogenic groups by capillary zone electrophoresis. The p<i>K</i><sub>a</sub> values of ionogenic groups of the above compounds were compared with those of the corresponding aminopurines. The p<i>K</i><sub>a</sub> of guanidino group at the purine moiety varies from 7.77 to 10.32. There is no protonation of N<sup>1</sup>-position in contrast to aminopurines. None of these compounds showed any antiviral activity. <p>

Title:Synthesis and Properties of 2-Guanidinopurines
Creators:
Česnek, Michal
Masojídková, Milena
Holý, Antonín
Šolínová, Veronika
Koval, Dušan
Kašička, Václav
Uncontrolled Keywords:Acyclic nucleoside phosphonates, Electrophoresis, PMEDAP analogues, Purines, Nucleosides, Guanidines, Basicity, Dissociation constants
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:71
Number:9
Page Range:pp. 1303-1319
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20061303UNSPECIFIED
ID Code:2543
Item Type:Article
Deposited On:06 Feb 2009 17:19
Last Modified:06 Feb 2009 16:19

Citation

Česnek, Michal; Masojídková, Milena; Holý, Antonín; Šolínová, Veronika; Koval, Dušan; Kašička, Václav (2006) Synthesis and Properties of 2-Guanidinopurines. Collection of Czechoslovak Chemical Communications, 71 (9). pp. 1303-1319. ISSN 0010-0765

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