5,7-Disubstituted-[1,2,4]triazolo[1,5- a ][1,3,5]triazines as pharmacological tools to explore the antagonist selectivity profiles toward adenosine receptors
Antonella Ciancetta
2
,
Nicola Porta
2
,
Sara Redenti
1
,
Giorgia Pastorin
3
,
Barbara Cacciari
4
,
K. Klotz
5
,
Stefano Moro
2
,
Giampiero Spalluto
1
Publication type: Journal Article
Publication date: 2016-01-01
scimago Q1
wos Q1
SJR: 1.142
CiteScore: 11.3
Impact factor: 5.9
ISSN: 02235234, 17683254
PubMed ID:
26717203
Organic Chemistry
Drug Discovery
General Medicine
Pharmacology
Abstract
The structure-activity relationship of new 5,7-disubstituted-[1,2,4]triazolo[1,5-a][1,3,5]triazines as adenosine receptors (ARs) antagonists has been explored. The introduction of a benzylamino group at C5 with a free amino group at C7 increases the affinity toward all the ARs subtypes (10: KihA1 = 94.6 nM; KihA2A = 1.11 nM; IC50hA2B = 2214 nM; KihA3 = 30.8 nM). Replacing the free amino group at C7 with a phenylureido moiety yields a potent and quite selective hA2A AR antagonist (14: hA2A AR Ki = 1.44 nM; hA1/hA2A = 216.0; hA3/hA2A = 20.6). This trend diverges from the analysis on the pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine series previously reported. With the help of an in silico receptor-driven approach, we have rationalized these observations and elucidated from a molecular point of view the role of the benzylamino group at C5 in determining affinity toward the hA2A AR.
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GOST
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Federico S. et al. 5,7-Disubstituted-[1,2,4]triazolo[1,5- a ][1,3,5]triazines as pharmacological tools to explore the antagonist selectivity profiles toward adenosine receptors // European Journal of Medicinal Chemistry. 2016. Vol. 108. pp. 529-541.
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Federico S., Ciancetta A., Porta N., Redenti S., Pastorin G., Cacciari B., Klotz K., Moro S., Spalluto G. 5,7-Disubstituted-[1,2,4]triazolo[1,5- a ][1,3,5]triazines as pharmacological tools to explore the antagonist selectivity profiles toward adenosine receptors // European Journal of Medicinal Chemistry. 2016. Vol. 108. pp. 529-541.
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TY - JOUR
DO - 10.1016/j.ejmech.2015.12.019
UR - https://doi.org/10.1016/j.ejmech.2015.12.019
TI - 5,7-Disubstituted-[1,2,4]triazolo[1,5- a ][1,3,5]triazines as pharmacological tools to explore the antagonist selectivity profiles toward adenosine receptors
T2 - European Journal of Medicinal Chemistry
AU - Federico, Stephanie
AU - Ciancetta, Antonella
AU - Porta, Nicola
AU - Redenti, Sara
AU - Pastorin, Giorgia
AU - Cacciari, Barbara
AU - Klotz, K.
AU - Moro, Stefano
AU - Spalluto, Giampiero
PY - 2016
DA - 2016/01/01
PB - Elsevier
SP - 529-541
VL - 108
PMID - 26717203
SN - 0223-5234
SN - 1768-3254
ER -
Cite this
BibTex (up to 50 authors)
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@article{2016_Federico,
author = {Stephanie Federico and Antonella Ciancetta and Nicola Porta and Sara Redenti and Giorgia Pastorin and Barbara Cacciari and K. Klotz and Stefano Moro and Giampiero Spalluto},
title = {5,7-Disubstituted-[1,2,4]triazolo[1,5- a ][1,3,5]triazines as pharmacological tools to explore the antagonist selectivity profiles toward adenosine receptors},
journal = {European Journal of Medicinal Chemistry},
year = {2016},
volume = {108},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/j.ejmech.2015.12.019},
pages = {529--541},
doi = {10.1016/j.ejmech.2015.12.019}
}