Synthesis and Cytotoxic Evaluation of 2-Aryl-7,8-dihydroquinolin-6(5H)-ones

Diego Díaz Bautista; Ever A. Blé González; Rosa María Chávez Santos; María Teresa Ramírez Apán; Miguel A. Vilchis Reyes; Roberto Martínez

doi:10.1055/s-0041-1738451

Synthesis, Table of Contents

Synthesis 2023; 55(22): 3809-3824
DOI: 10.1055/s-0041-1738451

paper

Synthesis and Cytotoxic Evaluation of 2-Aryl-7,8-dihydroquinolin-6(5H)-ones

Diego Díaz Bautista

^bDivisión Académica de Ciencias Básicas, Universidad Juárez Autónoma de Tabasco, Carretera Cunduacán-Jalpa Km 1, Col. La Esperanza, Cunduacán, C.P. 86690, Tabasco, Mexico

,

Ever A. Blé González∗

^bDivisión Académica de Ciencias Básicas, Universidad Juárez Autónoma de Tabasco, Carretera Cunduacán-Jalpa Km 1, Col. La Esperanza, Cunduacán, C.P. 86690, Tabasco, Mexico

,

Rosa María Chávez Santos

^aInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán, Ciudad de México, 04510, México

,

María Teresa Ramírez Apán

^aInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán, Ciudad de México, 04510, México

,

Miguel A. Vilchis Reyes

^bDivisión Académica de Ciencias Básicas, Universidad Juárez Autónoma de Tabasco, Carretera Cunduacán-Jalpa Km 1, Col. La Esperanza, Cunduacán, C.P. 86690, Tabasco, Mexico

,

Roberto Martínez ∗

^aInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán, Ciudad de México, 04510, México

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Abstract

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Abstract

Herein we present a facile four-step synthetic method for the synthesis of novel 2-aryl-substituted 7,8-dihydroquinolin-6(5H)-ones as cytotoxic agents. The key step was the use of Mannich salts derived from acetophenones as a Michael acceptor in the reaction with cyclohexane-1,4-dione monoethylene acetal to give 1,5-dicarbonyl compounds that were treated with ammonium acetate to give the 7,8-dihydroquinolin-6(5H)-ones. The cytotoxic activity of the synthesized compounds was evaluated against seven cell lines. The observed data showed good selectivity for chronic myeloid leukemia line K-562. The synthetic route was simple and applicable to various functional group containing substrates. These types of compounds may be utilized as lead compounds in cancer research and drug discovery.

Key words

7,8-dihydroquinolin-6(5H)-one - cytotoxic test - Mannich salts - leukemia - K-562 cell line

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References

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