Wiley
Journal of Pharmacy and Pharmacology
,  volume 74 ,  issue 6 ,  pages 887-895

Synthesis of 3,3-dimethyl-6-oxopyrano[3,4-c]pyridines and their antiplatelet and vasodilatory activity

Samvel N. Sirakanyan 1
, 
Marcel Hrubša 2
, 
Domenico Spinelli 3
, 
Patrícia Dias 2
, 
Victor Kartsev 4
, 
Alejandro Carazo 2
, 
Anush A. Hovakimyan 1
, 
Jana Pourová 2
, 
Elmira K. Hakobyan 1
, 
Jana Karlíčková 5
, 
Shamima Parvin 6
, 
Jaka Fadraersada 2
, 
Katerina Macakova 6
, 
Athina Geronikaki 7
, 
Přemysl Mladěnka 2
1
 
2
 
3
 
4
 
InterBioScreen , Moscow , Russia | 
5
 
6
 
7
 
Publication type: Journal Article
Publication date: 2021-06-09
Wiley
scimago Q2
wos Q2
SJR: 0.717
CiteScore: 6.1
Impact factor: 3.2
ISSN: 00223573, 20427158, 23282150
DOI:  10.1093/jpp/rgab075
PubMed ID:  34106261
Pharmacology
Pharmaceutical Science
Abstract
Objectives

Both pyridine and pyrano derivatives have been previously shown to possess biologically relevant activity. In this study, we report the incorporation of these two scaffolds into one molecule.

Methods

The designed 3,3-dimethyl-6-oxopyrano[3,4-c]pyridines were synthesized by the acylation of enamine under Stork conditions followed by condensation of formed β-diketones with 2-cyanoacetamide. The structures of these compounds were confirmed by using a wide spectrum of physico-chemical methods. Their antiplatelet, anticoagulant and vasodilatory activity together with toxicity were evaluated.

Key findings

A series of 6-oxopyrano[3,4-c]pyridines 3a–j was obtained. Four of these compounds were reported for the first time. None of the tested compounds demonstrated anticoagulant effect but 8-methyl derivative (3a) was a potent antiplatelet compound with IC50 numerically twice as low as the clinically used acetylsalicylic acid. A series of further mechanistic tests showed that 3a interferes with calcium signaling. The compound is also not toxic and in addition possesses vasodilatory activity as well.

Conclusions

Compound 3a is a promising inhibitor of platelet aggregation, whose mechanism of action should be studied in detail.

Found 
Found 

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GOST Copy
N. Sirakanyan S. et al. Synthesis of 3,3-dimethyl-6-oxopyrano[3,4-c]pyridines and their antiplatelet and vasodilatory activity // Journal of Pharmacy and Pharmacology. 2021. Vol. 74. No. 6. pp. 887-895.
GOST all authors (up to 50) Copy
N. Sirakanyan S., Hrubša M., Spinelli D., Dias P., Kartsev V., Carazo A., Hovakimyan A. A., Pourová J., Hakobyan E. K., Karlíčková J., Parvin S., Fadraersada J., Macakova K., Geronikaki A., Mladěnka P. Synthesis of 3,3-dimethyl-6-oxopyrano[3,4-c]pyridines and their antiplatelet and vasodilatory activity // Journal of Pharmacy and Pharmacology. 2021. Vol. 74. No. 6. pp. 887-895.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1093/jpp/rgab075
UR - https://doi.org/10.1093/jpp/rgab075
TI - Synthesis of 3,3-dimethyl-6-oxopyrano[3,4-c]pyridines and their antiplatelet and vasodilatory activity
T2 - Journal of Pharmacy and Pharmacology
AU - N. Sirakanyan, Samvel
AU - Hrubša, Marcel
AU - Spinelli, Domenico
AU - Dias, Patrícia
AU - Kartsev, Victor
AU - Carazo, Alejandro
AU - Hovakimyan, Anush A.
AU - Pourová, Jana
AU - Hakobyan, Elmira K.
AU - Karlíčková, Jana
AU - Parvin, Shamima
AU - Fadraersada, Jaka
AU - Macakova, Katerina
AU - Geronikaki, Athina
AU - Mladěnka, Přemysl
PY - 2021
DA - 2021/06/09
PB - Wiley
SP - 887-895
IS - 6
VL - 74
PMID - 34106261
SN - 0022-3573
SN - 2042-7158
SN - 2328-2150
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2021_N. Sirakanyan,
author = {Samvel N. Sirakanyan and Marcel Hrubša and Domenico Spinelli and Patrícia Dias and Victor Kartsev and Alejandro Carazo and Anush A. Hovakimyan and Jana Pourová and Elmira K. Hakobyan and Jana Karlíčková and Shamima Parvin and Jaka Fadraersada and Katerina Macakova and Athina Geronikaki and Přemysl Mladěnka},
title = {Synthesis of 3,3-dimethyl-6-oxopyrano[3,4-c]pyridines and their antiplatelet and vasodilatory activity},
journal = {Journal of Pharmacy and Pharmacology},
year = {2021},
volume = {74},
publisher = {Wiley},
month = {jun},
url = {https://doi.org/10.1093/jpp/rgab075},
number = {6},
pages = {887--895},
doi = {10.1093/jpp/rgab075}
}
MLA
Cite this
MLA Copy
N. Sirakanyan, Samvel, et al. “Synthesis of 3,3-dimethyl-6-oxopyrano[3,4-c]pyridines and their antiplatelet and vasodilatory activity.” Journal of Pharmacy and Pharmacology, vol. 74, no. 6, Jun. 2021, pp. 887-895. https://doi.org/10.1093/jpp/rgab075.