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Synthesis 2023; 55(22): 3809-3824
DOI: 10.1055/s-0041-1738451
DOI: 10.1055/s-0041-1738451
paper
Synthesis and Cytotoxic Evaluation of 2-Aryl-7,8-dihydroquinolin-6(5H)-ones
We acknowledge Consejo Nacional de Ciencia y Tecnología (grant A1-S-16584) and Dirección General de Asuntos del Personal Académico, Universidad Nacional Autónoma de México (grant IN204619) for financial support. D.D.B. thanks Consejo Nacional de Ciencia y Tecnología for a Ph.D. fellowship (CVU 788219).
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 lineSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1738451.
- Supporting Information
Publication History
Received: 29 April 2023
Accepted after revision: 10 July 2023
Article published online:
28 August 2023
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