Synthesis, biological studies and molecular modeling investigation
of 1,3-dimethyl-2,4-dioxo-6-methyl-8-(substituted) 1,2,3,4-tetrahydro
1,2,4-triazolo 3,4-f-purines as potential adenosine receptor
antagonists
G. Pastorin, C. Bolcato, B. Cacciari, S. Kachler, K. Klotz, C. Montopoli, S. Moro, and G. Spalluto. Farmaco, 60 (4):
299-306(April 2005)Pastorin, Giorgia Bolcato, Chiara Cacciari, Barbara Kachler, Sonja
Klotz, Karl-Norbert Montopoli, Christian Moro, Stefano Spalluto,
Giampiero Research Support, Non-U.S. Gov't Italy Farmaco (Societa
chimica italiana : 1989) Farmaco. 2005 Apr;60(4):299-306..
Abstract
A new series of potential adenosine receptor antagonists with a 1,2,4-triazolo-3,4-f-purine
structure have been synthesized, and their affinities at the four
adenosine receptor subtypes (A1, A2A, A2B and A3) have been evaluated.
The design was based on the demonstrated approach to novel A3 adenosine
receptor antagonists of adding a third ring to the xanthine structure.
Unfortunately, all the synthesized compounds were completely inactive
at all four adenosine receptor subtypes independently of their substitutions.
Preliminary molecular modeling investigation has demonstrated that
only a low degree of steric and electrostatic complementarity has
been observed for all the new synthesized triazolo-purines with respect
to other structurally related A3 receptor antagonists. This analysis
yielded valuable information about structure-activity relationships
and further design of potential adenosine receptor antagonists.
%0 Journal Article
%1 Pastorin2005a
%A Pastorin, G.
%A Bolcato, C.
%A Cacciari, B.
%A Kachler, S.
%A Klotz, K. N.
%A Montopoli, C.
%A Moro, S.
%A Spalluto, G.
%D 2005
%J Farmaco
%K & Adenylate Animals Binding Cell Cricetinae Cricetulus Cyclase/metabolism Cyclization Line Membrane/metabolism Models, Molecular P1/*antagonists Protein Purinergic Purines/*chemical Rats Relationship Sites Structure Structure-Activity Triazoles/*chemical inhibitors synthesis/chemistry/pharmacology Receptor
%N 4
%P 299-306
%T Synthesis, biological studies and molecular modeling investigation
of 1,3-dimethyl-2,4-dioxo-6-methyl-8-(substituted) 1,2,3,4-tetrahydro
1,2,4-triazolo 3,4-f-purines as potential adenosine receptor
antagonists
%U http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&dopt=Citation&list_uids=15848204
%V 60
%X A new series of potential adenosine receptor antagonists with a 1,2,4-triazolo-3,4-f-purine
structure have been synthesized, and their affinities at the four
adenosine receptor subtypes (A1, A2A, A2B and A3) have been evaluated.
The design was based on the demonstrated approach to novel A3 adenosine
receptor antagonists of adding a third ring to the xanthine structure.
Unfortunately, all the synthesized compounds were completely inactive
at all four adenosine receptor subtypes independently of their substitutions.
Preliminary molecular modeling investigation has demonstrated that
only a low degree of steric and electrostatic complementarity has
been observed for all the new synthesized triazolo-purines with respect
to other structurally related A3 receptor antagonists. This analysis
yielded valuable information about structure-activity relationships
and further design of potential adenosine receptor antagonists.
@article{Pastorin2005a,
abstract = {A new series of potential adenosine receptor antagonists with a [1,2,4]-triazolo-[3,4-f]-purine
structure have been synthesized, and their affinities at the four
adenosine receptor subtypes (A1, A2A, A2B and A3) have been evaluated.
The design was based on the demonstrated approach to novel A3 adenosine
receptor antagonists of adding a third ring to the xanthine structure.
Unfortunately, all the synthesized compounds were completely inactive
at all four adenosine receptor subtypes independently of their substitutions.
Preliminary molecular modeling investigation has demonstrated that
only a low degree of steric and electrostatic complementarity has
been observed for all the new synthesized triazolo-purines with respect
to other structurally related A3 receptor antagonists. This analysis
yielded valuable information about structure-activity relationships
and further design of potential adenosine receptor antagonists.},
added-at = {2010-12-14T18:12:02.000+0100},
author = {Pastorin, G. and Bolcato, C. and Cacciari, B. and Kachler, S. and Klotz, K. N. and Montopoli, C. and Moro, S. and Spalluto, G.},
biburl = {https://www.bibsonomy.org/bibtex/27e78ddc1c65a86309c699093fccc744b/pharmawuerz},
endnotereftype = {Journal Article},
interhash = {1caa25500de955ab5cc06a44842ef1b4},
intrahash = {7e78ddc1c65a86309c699093fccc744b},
issn = {0014-827X (Print) 0014-827X (Linking)},
journal = {Farmaco},
keywords = {& Adenylate Animals Binding Cell Cricetinae Cricetulus Cyclase/metabolism Cyclization Line Membrane/metabolism Models, Molecular P1/*antagonists Protein Purinergic Purines/*chemical Rats Relationship Sites Structure Structure-Activity Triazoles/*chemical inhibitors synthesis/chemistry/pharmacology Receptor},
month = Apr,
note = {Pastorin, Giorgia Bolcato, Chiara Cacciari, Barbara Kachler, Sonja
Klotz, Karl-Norbert Montopoli, Christian Moro, Stefano Spalluto,
Giampiero Research Support, Non-U.S. Gov't Italy Farmaco (Societa
chimica italiana : 1989) Farmaco. 2005 Apr;60(4):299-306.},
number = 4,
pages = {299-306},
shorttitle = {Synthesis, biological studies and molecular modeling investigation
of 1,3-dimethyl-2,4-dioxo-6-methyl-8-(substituted) 1,2,3,4-tetrahydro
[1,2,4]-triazolo [3,4-f]-purines as potential adenosine receptor
antagonists},
timestamp = {2010-12-14T18:20:07.000+0100},
title = {Synthesis, biological studies and molecular modeling investigation
of 1,3-dimethyl-2,4-dioxo-6-methyl-8-(substituted) 1,2,3,4-tetrahydro
[1,2,4]-triazolo [3,4-f]-purines as potential adenosine receptor
antagonists},
url = {http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&dopt=Citation&list_uids=15848204},
volume = 60,
year = 2005
}