Issue 69, 2020

Synthesis of dihydroisoindolo[2,1-a]quinolin-11-ones, their in silico ADMET properties and in vitro antitumor activities

Abstract

We evaluated the antitumoral activity of diverse series of 5-aryl-dihydroisoindolo[2,1-a]quinolin-11-ones, AIIQ (Aryl IsoIndolo-Quinoline, 4a–m), and 5-vinyl dihydroisoindolo[2,1-a]quinolin-11-ones, VIIQ (Vinyl IsoIndolo-Quinoline, 6a–l), obtained using three component imino Diels–Alder (DA) reaction of anilines, o-phthalaldehyde and dienophiles. The first series was obtained in previous work employing isoeugenol and anethole as dienophiles, whereas the vinyl series was synthesized in high yields (75–90%) using isoprene as a dienophile. The cytotoxic activity of both AIIQ and VIIQ series was evaluated against four cancer lines, identifying a new lead compound 4h from the AIIQ series, active against MCF-7 (310 nM), SKBR3 (1434 nM), PC3 (210 nM) and HeLa (79 nM) cells with high selectivity. In addition, in silico ADMET properties for the two series were assessed and discussed.

Graphical abstract: Synthesis of dihydroisoindolo[2,1-a]quinolin-11-ones, their in silico ADMET properties and in vitro antitumor activities

Supplementary files

Article information

Article type
Paper
Submitted
22 Maijs 2020
Accepted
06 Nov. 2020
First published
19 Nov. 2020
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2020,10, 42287-42296

Synthesis of dihydroisoindolo[2,1-a]quinolin-11-ones, their in silico ADMET properties and in vitro antitumor activities

D. R. Merchán-Arenas, F. Sojo, F. Arvelo and V. V. Kouznetsov, RSC Adv., 2020, 10, 42287 DOI: 10.1039/D0RA04555A

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