Synthesis of 4-Ethoxycarbonyl(cyano)-beta-Carbolines via Thermolysis of 4-Aryl-3(5)-Azidopyridine Derivatives and the Study of their Optical and Hypoglycemic Properties

Synthesis of 4-Ethoxycarbonyl(cyano)-beta-Carbolines via Thermolysis of 4-Aryl-3(5)-Azidopyridine Derivatives and the Study of their Optical and Hypoglycemic Properties Full article

Journal

Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353

Output data

Year: 2021, Volume: 57, Number: 2, Pages: 187-198 Pages count : 12 DOI: 10.1007/s10593-021-02892-9

Tags

azidopyridine; Hantzsch nitropyridines; pyrido[3,4-c]cinnoline; 9H-pyrido[3,4-b]indole; azo coupling; Cadogan reaction; cyclization

Authors

Proshchenkova Viktoriya A. ¹ , Shuvalov Vladislav Yu. ² , Glyzdinskaya Larisa V. ¹ , Fisyuk Alexander S. ² , Chernenko Sergei A. ¹ , Khvostov Mikhail V. ³ , Tolstikova Tatyana G. ³ , Vorontsova Marina A. ¹ , Sagitullina Galina P. ¹

Affiliations

1	(Данные Web of science) Dostoevsky Omsk State Univ, 55a Mira Ave, Omsk 644077, Russia
2	(Данные Web of science) Omsk State Tech Univ, 11 Mira Ave, Omsk 644050, Russia
3	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Akad Lavrentieva Ave, Novosibirsk 630090, Russia

4-Ethoxycarbonyl(cyano)-1,3-dimethyl-beta-carbolines were synthesized via thermolysis of 4-aryl-3(5)-azidopyridines and their optical and hypoglycemic properties were studied. For the first time, the accessible Hantzsch nitropyridines were used as the starting materials. Diazotization of 3-aminopyridines having a trimethoxyaryl substituent at the C-4 position of the pyridine ring by intramolecular azo coupling afforded 7,8,9-trimethoxy-2,4-dimethylpyrido[3,4-c]cinnolines. When evaluating the hypoglycemic properties of the four obtained beta-carbolines, it was found that ethyl 7-fluoro-1,3-dimethyl-9H-pyrido[3,4-b]indole-4-carboxylate, the structure of which contains the fluorine atom, has the highest glucose-lowering action.

Proshchenkova V.A. , Shuvalov V.Y. , Glyzdinskaya L.V. , Fisyuk A.S. , Chernenko S.A. , Khvostov M.V. , Tolstikova T.G. , Vorontsova M.A. , Sagitullina G.P.
Synthesis of 4-Ethoxycarbonyl(cyano)-beta-Carbolines via Thermolysis of 4-Aryl-3(5)-Azidopyridine Derivatives and the Study of their Optical and Hypoglycemic Properties
Chemistry of Heterocyclic Compounds. 2021. V.57. N2. P.187-198. DOI: 10.1007/s10593-021-02892-9 WOS Scopus РИНЦ OpenAlex

Published print:	Feb 1, 2021
Published online:	Mar 3, 2021

Web of science:	WOS:000624405400003
Scopus:	2-s2.0-85102032216
Elibrary:	46759989
OpenAlex:	W3134865102

DB	Citing
Web of science	4
Scopus	4
Elibrary	6
OpenAlex	5