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Paper | Regular issue | Vol 104, No. 5, 2022, pp.894-916
Published online, 9th February, 2022
DOI: 10.3987/COM-21-14602
Synthesis of Hexahydroquinoline-3-carboxamide Derivatives and Their HIV-1 Antiviral Activity

Reagan Lehlogonolo Mohlala, Elena Mabel Coyanis,* Muhammad Qasim Fish, and Moira Leanne Bode*

*Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Private Bag 3, PO Wits, Johannesburg, 2050, South Africa

Abstract

Computational modelling was used to identify scaffolds with the potential to disrupt the interaction between HIV-1 integrase and lens epithelium-derived growth factor (HIV-1-IN-LEDGF/p75). Virtual screening of commercial library collections led to the identification of N-(4-chlorophenyl)-7,7-dimethyl-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxamide as a promising candidate. The synthesis of this compound and its derivatives involved the reaction of the corresponding carboxylic acid derivatives with aniline in the presence of coupling agent carbonyldiimidazole (CDI). This gave rise to N-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxamides in yields of 71-85%. These compounds were found to be non-toxic in an MT4 cell line at 100 μM and were subsequently evaluated for antiviral activity in infected MT4 cells at a single dose concentration of 100 μM.