Home / Publications / Synthesis of new heterocyclic systems fused at pyrazolo[3,4-c]-2,7-naphthyridine core

Synthesis of new heterocyclic systems fused at pyrazolo[3,4-c]-2,7-naphthyridine core

Samvel N Sirakanyan 1
Samvel N Sirakanyan
Elmira K Hakobyan 1
Elmira K Hakobyan
Domenico Spinelli 2
Domenico Spinelli
Athina Geronikaki 3
Athina Geronikaki
Victor Georgievich Kartsev 4
Victor Georgievich Kartsev
Hasmik A Yegoryan 1
Hasmik A Yegoryan
Anush A Hovakimyan 1
Anush A Hovakimyan
2 Dipartimento di Chimica ''G. Ciamician'', Universita degli Studi di Bologna, Bologna, Italy
4 'InterBioScreen Ltd.', Chernogolovka, Moscow Region, Russian Federation
Published 2022-04-29
CommunicationVolume 32, Issue 3, 393-394
1
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Sirakanyan S. N. et al. Synthesis of new heterocyclic systems fused at pyrazolo[3,4-c]-2,7-naphthyridine core // Mendeleev Communications. 2022. Vol. 32. No. 3. pp. 393-394.
GOST all authors (up to 50) Copy
Sirakanyan S. N., Hakobyan E. K., Spinelli D., Geronikaki A., Kartsev V. G., Yegoryan H. A., Hovakimyan A. A. Synthesis of new heterocyclic systems fused at pyrazolo[3,4-c]-2,7-naphthyridine core // Mendeleev Communications. 2022. Vol. 32. No. 3. pp. 393-394.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2022.05.034
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.034
TI - Synthesis of new heterocyclic systems fused at pyrazolo[3,4-c]-2,7-naphthyridine core
T2 - Mendeleev Communications
AU - Sirakanyan, Samvel N
AU - Hakobyan, Elmira K
AU - Spinelli, Domenico
AU - Geronikaki, Athina
AU - Kartsev, Victor Georgievich
AU - Yegoryan, Hasmik A
AU - Hovakimyan, Anush A
PY - 2022
DA - 2022/04/29
PB - Mendeleev Communications
SP - 393-394
IS - 3
VL - 32
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2022_Sirakanyan,
author = {Samvel N Sirakanyan and Elmira K Hakobyan and Domenico Spinelli and Athina Geronikaki and Victor Georgievich Kartsev and Hasmik A Yegoryan and Anush A Hovakimyan},
title = {Synthesis of new heterocyclic systems fused at pyrazolo[3,4-c]-2,7-naphthyridine core},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.034},
number = {3},
pages = {393--394},
doi = {10.1016/j.mencom.2022.05.034}
}
MLA
Cite this
MLA Copy
Sirakanyan, Samvel N., et al. “Synthesis of new heterocyclic systems fused at pyrazolo[3,4-c]-2,7-naphthyridine core.” Mendeleev Communications, vol. 32, no. 3, Apr. 2022, pp. 393-394. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.034.

Keywords

2,7-naphthyridines
acetylacetone
heterocyclization
hydrazine
pyrazolo[3,4-c][1,2,4]triazolo[3,4-a]-2,7- naphthyridines
pyrazolo[3,4-c]tetrazolo[5,1-a]-2,7-naphthyridine
pyrimido[1' 2':1,5]pyrazolo[3,4-c]-2,7-naphthyridine

Abstract

Efficient syntheses of new heterocyclic systems comprising pyrimido[1',2':1,5]pyrazolo[3,4-c]-2,7-naphthyridine, pyrazolo[3,4-c][1,2,4]triazolo[3,4-a]-2,7-naphthyridine and pyrazolo[3,4-c]tetrazolo[5,1-a]-2,7-naphthyridine cores were performed in two simple steps. In the first step, pyrazole ring was fused at the 2-chloro-3-cyanopyridine moiety by treatment with hydrazine. In the second step, pyrimidine part was fused at the thus formed 3-aminopyrazole moiety by heterocyclization with acetylacetone.

References

1.
(a) E. G. Brown, Ring Nitrogen and Key Biomolecules: The Biochemistry of N-Heterocycles, Springer, Dordrecht, 1998; (b) S. Hauptmann and A. Speicher, The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications, Wiley-VCH, Weinheim, 2012.
2.
Synthesis and Anticonvulsant Activity of Pyrazolo[3,4-b]pyrano(thiopyrano)[4,3-d]pyridine and Pyrazolo[3,4-c]isoquinoline Derivatives
Paronikyan E.G., Sirakanyan S.N., Noravyan A.S., Paronikyan R.G., Dzhagatspanyan I.A.
Pharmaceutical Chemistry Journal, 2001
4.
BAY 41-2272 [5-Cyclopropyl-2-[1-(2-fluoro-benzyl)-1H-pyrazolo[3,4-b]pyridine-3-yl]pyrimidin-4-ylamine]-Induced Dilation in Ovine Pulmonary Artery: Role of Sodium Pump
Bawankule D.U., Sathishkumar K., Sardar K.K., Chanda D., Krishna A.V., Prakash V.R., Mishra S.K.
Journal of Pharmacology and Experimental Therapeutics, 2005
5.
Synthesis and antiviral activity of new 4-(phenylamino)/4-[(methylpyridin-2-yl)amino]-1-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acids derivatives
Bernardino A.M., de Azevedo A.R., Pinheiro L.C., Borges J.C., Carvalho V.L., Miranda M.D., de Meneses M.D., Nascimento M., Ferreira D., Rebello M.A., Silva V.A., de Frugulhetti I.C.
Medicinal Chemistry Research, 2007
6.
Antileishmanial Pyrazolopyridine Derivatives:  Synthesis and Structure−Activity Relationship Analysis
de Mello H., Echevarria A., Bernardino A.M., Canto-Cavalheiro M., Leon L.L.
Journal of Medicinal Chemistry, 2004
8.
Fragment based lead discovery of small molecule inhibitors for the EPHA4 receptor tyrosine kinase
van Linden O.P., Farenc C., Zoutman W.H., Hameetman L., Wijtmans M., Leurs R., Tensen C.P., Siegal G., de Esch I.J.
European Journal of Medicinal Chemistry, 2012
9.
Synthesis of 3-(1H-benzimidazol-2-yl)-5-isoquinolin-4-ylpyrazolo[1,2-b]pyridine, a potent cyclin dependent kinase 1 (CDK1) inhibitor
Huang S., Lin R., Yu Y., Lu Y., Connolly P.J., Chiu G., Li S., Emanuel S.L., Middleton S.A.
Bioorganic and Medicinal Chemistry Letters, 2007
10.
Identification of 1H-pyrazolo[3,4-b]pyridine derivatives as potent ALK-L1196M inhibitors
Nam Y., Hwang D., Kim N., Seo H., Selim K.B., Sim T.
Journal of Enzyme Inhibition and Medicinal Chemistry, 2019
11.
Synthesis of novel 1H-Pyrazolo[3,4-b]pyridine derivatives as DYRK 1A/1B inhibitors
Park A., Hwang J., Lee J., Heo E.J., Na Y., Kang S., Jeong K., Kim K.Y., Shin S.J., Lee H.
Bioorganic and Medicinal Chemistry Letters, 2021
13.
(b) K. P. Tiwari, P. K. Minocha and M. Masood, Pol. J. Chem., 1980, 54, 857
16.
(e) E. G. Paronikyan, G. V. Mirzoyan, A. S. Noravyan, E. M. Arzanunts, R. S. Sukasyan, I. S. Sarkisyan, I. M. Nazaryan and I. A. Dzhagatspanyan, Pharm. Chem. J., 1997, 31, 540 [Khim.-Farm. Zh., 1997, 31 (10), 34]
17.
Synthesis and Anticonvulsant Activity of isothiazolo[5,4-b]pyrano(thiopyrano)[4,3-d]pyridine and Isothiazolo[4,5-b]-2,7-naphthyridine Derivatives
Paronikyan E.G., Noravyan A.S., Dzhagatspanyan I.A., Nazaryan I.M., Paronikyan R.G.
Pharmaceutical Chemistry Journal, 2002
18.
(a) E. G. Paronikyan, S. N. Sirakanyan, A. S. Noravyan, T. O. Asatryan, K. J. Markaryan and R. A. Aleksanyan, Pharm. Chem. J., 1996, 30, 365 [Khim.-Farm. Zh., 1996, 30 (6), 13]
19.
Synthesis and Neurotropic Activity of Triazolo[3,4-a]-and Triazolo[5,1-a][2,7]Naphthyridines
Sirakanyan S.N., Tonoyants N.A., Noravyan A.S., Dzhagatspanyan I.A., Nazaryan I.M., Akopyan A.G., Paronikyan R.G., Minasyan N.S.
Pharmaceutical Chemistry Journal, 2014
20.
Synthesis and Neurotropic Activity of New 7-Cyclohexyl-6,7,8,9-Tetrahydro-3H-Pyrazolo[3,4-c]-2,7-Naphthyridine-1,5-Diamines
Sirakanyan S.N., Hakobyan E.K., Nikoghosyan A.G., Paronikyan R.G., Dzhagatspanyan I.A., Nazaryan I.M., Akopyan A.G., Hovakimyan A.A.
Pharmaceutical Chemistry Journal, 2018
21.
On the reactivity of 4-cyano-1,3-dichloro-7-methyl-5,6,7,8-tetrahydro-2,7-naphthyridine with several amines in different experimental conditions: monosubstitution, disubstitution, and a new unexpected rearrangement
23.
New heterocyclic systems derived from pyridine: new substrates for the investigation of the azide/tetrazole equilibrium
Sirakanyan S.N., Spinelli D., Geronikaki A., Hovakimyan A.A., Noravyan A.S.
Tetrahedron, 2014