Home / Publications / New type of recyclization in 3,4-dihydroisoquinolines in the synthesis of β-(o-indazolylaryl)ethylamines and their 7-azaindazolyl analogues

New type of recyclization in 3,4-dihydroisoquinolines in the synthesis of β-(o-indazolylaryl)ethylamines and their 7-azaindazolyl analogues

Alexander Aleksandrovich Zubenko 1
Alexander Aleksandrovich Zubenko
Anatolii Savel'evich Morkovnik 2
Anatolii Savel'evich Morkovnik
Lyudmila Nikolaevna Divaeva 2
Lyudmila Nikolaevna Divaeva
Vadim Sergeevich Sochnev 2
Vadim Sergeevich Sochnev
Alexander Ivanovich Klimenko 1
Alexander Ivanovich Klimenko
Leonid Nikolaevich Fetisov 1
Leonid Nikolaevich Fetisov
Anatolii Nikolaevich Bodryakov 1
Anatolii Nikolaevich Bodryakov
Marya Anatol'evna Bodryakova 1
Marya Anatol'evna Bodryakova
Gennadii Sergeevich Borodkin 2
Gennadii Sergeevich Borodkin
Published 2022-03-06
CommunicationVolume 32, Issue 2, 265-267
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Zubenko A. A. et al. New type of recyclization in 3,4-dihydroisoquinolines in the synthesis of β-(o-indazolylaryl)ethylamines and their 7-azaindazolyl analogues // Mendeleev Communications. 2022. Vol. 32. No. 2. pp. 265-267.
GOST all authors (up to 50) Copy
Zubenko A. A., Morkovnik A. S., Divaeva L. N., Sochnev V. S., Demidov O. P., Klimenko A. I., Fetisov L. N., Bodryakov A. N., Bodryakova M. A., Borodkin G. S. New type of recyclization in 3,4-dihydroisoquinolines in the synthesis of β-(o-indazolylaryl)ethylamines and their 7-azaindazolyl analogues // Mendeleev Communications. 2022. Vol. 32. No. 2. pp. 265-267.
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TY - JOUR
DO - 10.1016/j.mencom.2022.03.038
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.038
TI - New type of recyclization in 3,4-dihydroisoquinolines in the synthesis of β-(o-indazolylaryl)ethylamines and their 7-azaindazolyl analogues
T2 - Mendeleev Communications
AU - Zubenko, Alexander Aleksandrovich
AU - Morkovnik, Anatolii Savel'evich
AU - Divaeva, Lyudmila Nikolaevna
AU - Sochnev, Vadim Sergeevich
AU - Demidov, Oleg Petrovich
AU - Klimenko, Alexander Ivanovich
AU - Fetisov, Leonid Nikolaevich
AU - Bodryakov, Anatolii Nikolaevich
AU - Bodryakova, Marya Anatol'evna
AU - Borodkin, Gennadii Sergeevich
PY - 2022
DA - 2022/03/06
PB - Mendeleev Communications
SP - 265-267
IS - 2
VL - 32
ER -
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@article{2022_Zubenko,
author = {Alexander Aleksandrovich Zubenko and Anatolii Savel'evich Morkovnik and Lyudmila Nikolaevna Divaeva and Vadim Sergeevich Sochnev and Oleg Petrovich Demidov and Alexander Ivanovich Klimenko and Leonid Nikolaevich Fetisov and Anatolii Nikolaevich Bodryakov and Marya Anatol'evna Bodryakova and Gennadii Sergeevich Borodkin},
title = {New type of recyclization in 3,4-dihydroisoquinolines in the synthesis of β-(o-indazolylaryl)ethylamines and their 7-azaindazolyl analogues},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.038},
number = {2},
pages = {265--267},
doi = {10.1016/j.mencom.2022.03.038}
}
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Zubenko, Alexander Aleksandrovich, et al. “New type of recyclization in 3,4-dihydroisoquinolines in the synthesis of β-(o-indazolylaryl)ethylamines and their 7-azaindazolyl analogues.” Mendeleev Communications, vol. 32, no. 2, Mar. 2022, pp. 265-267. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.038.

Keywords

1-(2-hydrazinoaryl)-3,4-dihydroisoquinolines
7-azaindazoles
b-phenylethylamines
indazoles
isoquinolines
recyclization

Abstract

1-(2-Hydrazinoaryl)-3,4-dihydroisoquinolines and their hydrazinopyridyl analogues undergo recyclization affording novel (7-aza)indazolyl-β-arylethylamines. The products are expected to possess neurotropic activities.

References

1.
Indazole as a Privileged Scaffold: The Derivatives and their Therapeutic Applications
Qin J., Cheng W., Duan Y., Yang H., Yao Y.
Anti-Cancer Agents in Medicinal Chemistry, 2020
2.
Synthesis and antibacterial activity of some novel pyrazolopyridine derivatives
Panda N., Karmakar S., Jena A.K.
Chemistry of Heterocyclic Compounds, 2011
3.
A Novel Pyrazolopyridine with in Vivo Activity in Plasmodium berghei- and Plasmodium falciparum-Infected Mouse Models from Structure–Activity Relationship Studies around the Core of Recently Identified Antimalarial Imidazopyridazines
Le Manach C., Paquet T., Brunschwig C., Njoroge M., Han Z., Gonzàlez Cabrera D., Bashyam S., Dhinakaran R., Taylor D., Reader J., Botha M., Churchyard A., Lauterbach S., Coetzer T.L., Birkholtz L., et. al.
Journal of Medicinal Chemistry, 2015
4.
Decrypting Cryptosporidium
Villanueva M.T.
Nature Reviews Drug Discovery, 2017
5.
A Cryptosporidium PI(4)K inhibitor is a drug candidate for cryptosporidiosis
Manjunatha U.H., Vinayak S., Zambriski J.A., Chao A.T., Sy T., Noble C.G., Bonamy G.M., Kondreddi R.R., Zou B., Gedeck P., Brooks C.F., Herbert G.T., Sateriale A., Tandel J., Noh S., et. al.
Nature, 2017
6.
Pyrazolopyrimidines as dual Akt/p70S6K inhibitors
Rice K.D., Kim M.H., Bussenius J., Anand N.K., Blazey C.M., Bowles O.J., Canne-Bannen L., Chan D.S., Chen B., Co E.W., Costanzo S., DeFina S.C., Dubenko L., Engst S., Franzini M., et. al.
Bioorganic and Medicinal Chemistry Letters, 2012
7.
Synthesis and bioactivity of novel amino-pyrazolopyridines.
Orlikova B., Chaouni W., Schumacher M., Aadil M., Diederich M., Kirsch G.
European Journal of Medicinal Chemistry, 2014
8.
Microwave-assisted synthesis of some new pyrazolopyridines and their antioxidant, antitumor and antimicrobial activities
El-Borai M.A., Rizk H.F., Beltagy D.M., El-Deeb I.Y.
European Journal of Medicinal Chemistry, 2013
9.
Synthesis and structure-activity relationships of a series of anxioselective pyrazolopyridine ester and amide anxiolytic agents
Bare T.M., McLaren C.D., Campbell J.B., Firor J.W., Resch J.F., Walters C.P., Salama A.I., Meiners B.A., Patel J.B.
Journal of Medicinal Chemistry, 1989
10.
Antiplatelet pyrazolopyridines derivatives: pharmacological, biochemical and toxicological characterization
Saito M.S., Lourenço A.L., Dias L.R., Freitas A.C., Vitorino M.I., Albuquerque M.G., Rodrigues C.R., Cabral L.M., Dias E.P., Castro H.C., Satlher P.C.
Journal of Enzyme Inhibition and Medicinal Chemistry, 2016
11.
Pyrrolopyridine or Pyrazolopyridine Derivatives
12.
Pyrazolopyridines as a novel structural class of potent and selective PDE4 inhibitors
Hamblin J.N., Angell T.D., Ballantine S.P., Cook C.M., Cooper A.W., Dawson J., Delves C.J., Jones P.S., Lindvall M., Lucas F.S., Mitchell C.J., Neu M.Y., Ranshaw L.E., Solanke Y.E., Somers D.O., et. al.
Bioorganic and Medicinal Chemistry Letters, 2008
13.
Discovery of Potent and Selective Non-Nucleotide Small Molecule Inhibitors of CD73
Beatty J.W., Lindsey E.A., Thomas-Tran R., Debien L., Mandal D., Jeffrey J.L., Tran A.T., Fournier J., Jacob S.D., Yan X., Drew S.L., Ginn E., Chen A., Pham A.T., Zhao S., et. al.
Journal of Medicinal Chemistry, 2020
14.
DrugBank, https://www.drugbank.com.
15.
Synthesis and Biological Evaluation of 3‐Arylindazoles as Selective MEK4 Inhibitors
Deibler K.K., Schiltz G.E., Clutter M.R., Mishra R.K., Vagadia P.P., O'Connor M., George M.D., Gordon R., Fowler G., Bergan R., Scheidt K.A.
ChemMedChem, 2019
16.
Protopopov M.V., Vdovin V.S., Lukashov S.S., Ostrynska O.V., Borysenko I.P., Borovykov O.V., Starosyla S.A., Bilokin Y.V., Kukharenko O.P., Bdzhola V.G., Yarmoluk S.M.
Biopolymers and Cell, 2020
17.
Synthesis of 3-Arylindazole-1-acetic Acids and In Vitro Study of Potential Antibacterial Effect
Chattha F.A., Kousar S., Mehr-un-Nisa, Munawar M.A.
Letters in Drug Design and Discovery, 2018
18.
Recent synthetic approaches to 1H- and 2H-indazoles (microreview)
Rai G.S., Maru J.J.
Chemistry of Heterocyclic Compounds, 2020
19.
Trace Amines and Neurological Disorders: Potential Mechanisms and Risk Factors, eds. T. Farooqui and A. A. Farooqui, Elsevier, 2016.
20.
Zubenko A.A., Morkovnik A.S., Divaeva L.N., Demidov O.P., Kartsev V.G., Sochnev V.S., Klimenko A.I., Dobaeva N.M., Borodkin G.S., Bodryakov A.N., Bodryakova M.A., Fetisov L.N.
Mendeleev Communications, 2021
21.
A. A. Zubenko, A. S. Morkovnik, L. N. Divaeva, V. S. Sochnev, O. P. Demidov, A. N. Bodryakov, L. N. Fetisov, K. N. Kononenko, M. A. Bodryakova and A. I. Klimenko, Russ. J. Gen. Chem., 2021, 91, (Zh. Obshch. Khim., 2021, 91, 703).
22.
Zubenko A.A., Morkovnik A.S., Divaeva L.N., Demidov O.P., Sochnev V.S., Borodkina I.G., Drobin Y.D., Spasov A.A.
Mendeleev Communications, 2020
23.
Synthesis of indazole motifs and their medicinal importance: An overview
Gaikwad D.D., Chapolikar A.D., Devkate C.G., Warad K.D., Tayade A.P., Pawar R.P., Domb A.J.
European Journal of Medicinal Chemistry, 2015
24.
Synthesis of fluorinated indazoles through ANRORC-like rearrangement of 1,2,4-oxadiazoles with hydrazine
Palumbo Piccionello A., Pace A., Pibiri I., Buscemi S., Vivona N.
Tetrahedron, 2006
25.
On the reaction of some 5-polyfluoroaryl-1,2,4-oxadiazoles with methylhydrazine: synthesis of fluorinated indazoles
Palumbo Piccionello A., Pace A., Pierro P., Pibiri I., Buscemi S., Vivona N.
Tetrahedron, 2009
27.
Electron transfer in the peroxytrifluoroacetic acid-assisted sulfoxidation and oxidative destruction of benzhydryl sulfides
29.
SHELXT– Integrated space-group and crystal-structure determination
Sheldrick G.M.
Acta Crystallographica Section A: Foundations and Advances, 2015
30.
G. M. Sheldrick, Acta Crystallogr., 2015, C71, 3.
31.
OLEX2: a complete structure solution, refinement and analysis program
Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A., Puschmann H.
Journal of Applied Crystallography, 2009