Synthesis of new hybrid molecules based on 7-hydroxy-2,2,4-trimethylhydroquinoline derivatives

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Abstract

Among the fused azaheterocycles, quinolines have long attracted the attention of chemists. First of all, this is due to their wide range of practically useful properties. Quinolines and their derivatives exhibit a wide range of biological activities, including antimalarial, anticancer, antiviral, antifungal and anti-infl ammatory activities. These compounds are also used as fl uorescent probes, luminescent labels, and in dye production. In the course of this work, a series of pyridocoumarin systems have been obtained, which have been tested as inhibitors of blood clotting factors Xa and XIa. The method for the synthesis of the proposed compounds involves the condensation of 7-hydroxy-2,2,4-trimethyl-1,2- dihydroquinolines and 7-hydroxy-2,2,4-trimethyl-1,2,3,4-tetrahydroquinolines with malononitrile and aryl(hetaryl)aldehydes. It has been found that as a result of this interaction, new 4H-pyrano[3,2-g]quinoline-3-carbonitriles are formed. In addition, new derivatives of 7-hydroxy-2,2,4- trimethyl-1,2,3,4-tetrahydroquinoline containing an aryl fragment in the 4-position have been obtained, which have been also used as starting compounds for the annelation reaction of the pyran ring. The pyridocoumarin systems obtained in the study have showed promising inhibitory activity against these coagulation factors, making them promising candidates for further study as potential anticoagulant drugs.

About the authors

Yana Aleksandrovna Gribanova

Voronezh State University

ORCID iD: 0009-0003-1704-6873
Universitetskaya sq., 1, Voronezh, Voronezh region, 394036

Andrey Yur'evich Potapov

Voronezh State University

ORCID iD: 0000-0001-8084-530X
Universitetskaya sq., 1, Voronezh, Voronezh region, 394036

Kristina Olegovna Karelina

Voronezh State University

ORCID iD: 0009-0003-7430-5966
Universitetskaya sq., 1, Voronezh, Voronezh region, 394036

Aleksei I. Slivkin

Voronezh State University

Universitetskaya sq., 1, Voronezh, Voronezh region, 394036

Khidmet S. Shikhaliev

Voronezh State University

Universitetskaya sq., 1, Voronezh, Voronezh region, 394036

Error Fedorovich Error

Voronezh State University

Universitetskaya sq., 1, Voronezh, Voronezh region, 394036

Error Borisovich Error

Воронежский государственный технический университет

ул. 20-летия Октября, 84

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