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Issue 130, 2015
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Regioselective Suzuki–Miyaura reactions of 4,7-dichloro-N-methylisatin. Synthesis, anti-HIV activity and modeling study

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Abstract

Suzuki–Miyaura reactions of 4,7-dichloro-N-methylisatin provide a convenient access to arylated methylisatins. The reactions proceed with excellent site-selectivity in favour of position 4, due to electronic reasons. All the new compounds were evaluated in vitro for their antiviral activity against the replication of HIV-1 and HIV-2 in MT4 cells using a MTT assay. 4-(4-Acetylphenyl)-7-chloro-1-methylindoline-2,3-dione (8l), containing an acetyl group located at carbon C(4) of the isatin backbone, showed an IC50 value of >3.47 μM against HIV-2 with a therapeutic index (SI) of 4. This means that 8l was cytotoxic to MT-4 cells at a CC50 value of 13.43 μM; also 4,7-dichloro-1-methylindoline-2,3-dione (5), 7-chloro-4-(4-chlorophenyl)-1-methylindoline-2,3-dione (8c), 7-chloro-4-(4-ethoxyphenyl)-1-methylindoline-2,3-dione (8g) and 7-chloro-1-methyl-4-(4-vinylphenyl)indoline-2,3-dione (8m) were cytotoxic to MT-4 cells within a 2.21–3.11 μM concentration range. In a docking study, 8l interacted with several amino acids in the reverse transcriptase (RT) binding site of HIV-2.

Graphical abstract: Regioselective Suzuki–Miyaura reactions of 4,7-dichloro-N-methylisatin. Synthesis, anti-HIV activity and modeling study

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Supplementary files

Article information


Submitted
20 Aug 2015
Accepted
04 Dec 2015
First published
07 Dec 2015

RSC Adv., 2015,5, 107360-107369
Article type
Paper
Author version available

Regioselective Suzuki–Miyaura reactions of 4,7-dichloro-N-methylisatin. Synthesis, anti-HIV activity and modeling study

A. M. Hamdy, N. A. Al-Masoudi, C. Pannecouque, Q. Rahman, A. Villinger and P. Langer, RSC Adv., 2015, 5, 107360
DOI: 10.1039/C5RA16841D

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