Synthesis, biological and modeling studies of 1,3-di-n-propyl-2,4-dioxo-6-methyl-8-(substituted)
1,2,3,4-tetrahydro 1,2,4-triazolo 3,4-f-purines as adenosine
receptor antagonists
G. Pastorin, C. Bolcato, B. Cacciari, S. Kachler, K. Klotz, C. Montopoli, S. Moro, and G. Spalluto. Farmaco, 60 (8):
643-51(August 2005)Pastorin, G Bolcato, C Cacciari, B Kachler, S Klotz, K-N Montopoli,
C Moro, S Spalluto, G Research Support, Non-U.S. Gov't France Farmaco
(Societa chimica italiana : 1989) Farmaco. 2005 Aug;60(8):643-51..
Abstract
A new series of potential adenosine receptor antagonists with a 1,2,4-triazolo-3,4-f-purine
structure bearing at the 1 and 3 position n-propyl groups have been
synthesized, and their affinities at the four human adenosine receptor
subtypes (A(1), A(2A), A(2B) and A(3)) have been evaluated. In this
case the presence of n-propyl groups seems to induce potency at the
A(2A) and A(3) adenosine receptor subtypes as opposed to our previously
reported series bearing methyl substituents at the 1 and 3 positions.
In particular the non-acylated derivative 17 showed affinity at these
two receptor subtypes in the micromolar range. Indeed, preliminary
molecular modeling investigations according to the experimental binding
data indicate a modest steric and electrostatic antagonist-receptor
complementarity.
Synthesis, biological and modeling studies of 1,3-di-n-propyl-2,4-dioxo-6-methyl-8-(substituted)
1,2,3,4-tetrahydro 1,2,4-triazolo 3,4-f-purines as adenosine
receptor antagonists
Pastorin, G Bolcato, C Cacciari, B Kachler, S Klotz, K-N Montopoli,
C Moro, S Spalluto, G Research Support, Non-U.S. Gov't France Farmaco
(Societa chimica italiana : 1989) Farmaco. 2005 Aug;60(8):643-51.
%0 Journal Article
%1 Pastorin2005
%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 & *Drug *Purines/chemical A1/antagonists A2A/antagonists A2B/antagonists A3/*antagonists Adenosine Binding Conformation Design Drug Evaluation, Humans Models, Molecular Preclinical Protein Rats Relationship Secondary Sites Structure Structure, Structure-Activity inhibitors synthesis/chemistry/pharmacology Receptor
%N 8
%P 643-51
%T Synthesis, biological and modeling studies of 1,3-di-n-propyl-2,4-dioxo-6-methyl-8-(substituted)
1,2,3,4-tetrahydro 1,2,4-triazolo 3,4-f-purines as adenosine
receptor antagonists
%U http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&dopt=Citation&list_uids=15961085
%V 60
%X A new series of potential adenosine receptor antagonists with a 1,2,4-triazolo-3,4-f-purine
structure bearing at the 1 and 3 position n-propyl groups have been
synthesized, and their affinities at the four human adenosine receptor
subtypes (A(1), A(2A), A(2B) and A(3)) have been evaluated. In this
case the presence of n-propyl groups seems to induce potency at the
A(2A) and A(3) adenosine receptor subtypes as opposed to our previously
reported series bearing methyl substituents at the 1 and 3 positions.
In particular the non-acylated derivative 17 showed affinity at these
two receptor subtypes in the micromolar range. Indeed, preliminary
molecular modeling investigations according to the experimental binding
data indicate a modest steric and electrostatic antagonist-receptor
complementarity.
@article{Pastorin2005,
abstract = {A new series of potential adenosine receptor antagonists with a [1,2,4]-triazolo-[3,4-f]-purine
structure bearing at the 1 and 3 position n-propyl groups have been
synthesized, and their affinities at the four human adenosine receptor
subtypes (A(1), A(2A), A(2B) and A(3)) have been evaluated. In this
case the presence of n-propyl groups seems to induce potency at the
A(2A) and A(3) adenosine receptor subtypes as opposed to our previously
reported series bearing methyl substituents at the 1 and 3 positions.
In particular the non-acylated derivative 17 showed affinity at these
two receptor subtypes in the micromolar range. Indeed, preliminary
molecular modeling investigations according to the experimental binding
data indicate a modest steric and electrostatic antagonist-receptor
complementarity.},
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/2ffae8adc25f63b281bf174b9094534d6/pharmawuerz},
endnotereftype = {Journal Article},
interhash = {1a310863144732f454ae9b06030c1df0},
intrahash = {ffae8adc25f63b281bf174b9094534d6},
issn = {0014-827X (Print) 0014-827X (Linking)},
journal = {Farmaco},
keywords = {& *Drug *Purines/chemical A1/antagonists A2A/antagonists A2B/antagonists A3/*antagonists Adenosine Binding Conformation Design Drug Evaluation, Humans Models, Molecular Preclinical Protein Rats Relationship Secondary Sites Structure Structure, Structure-Activity inhibitors synthesis/chemistry/pharmacology Receptor},
month = Aug,
note = {Pastorin, G Bolcato, C Cacciari, B Kachler, S Klotz, K-N Montopoli,
C Moro, S Spalluto, G Research Support, Non-U.S. Gov't France Farmaco
(Societa chimica italiana : 1989) Farmaco. 2005 Aug;60(8):643-51.},
number = 8,
pages = {643-51},
shorttitle = {Synthesis, biological and modeling studies of 1,3-di-n-propyl-2,4-dioxo-6-methyl-8-(substituted)
1,2,3,4-tetrahydro [1,2,4]-triazolo [3,4-f]-purines as adenosine
receptor antagonists},
timestamp = {2010-12-14T18:20:21.000+0100},
title = {Synthesis, biological and modeling studies of 1,3-di-n-propyl-2,4-dioxo-6-methyl-8-(substituted)
1,2,3,4-tetrahydro [1,2,4]-triazolo [3,4-f]-purines as adenosine
receptor antagonists},
url = {http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&dopt=Citation&list_uids=15961085},
volume = 60,
year = 2005
}