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. 2018 Jan 30;23(2):286.
doi: 10.3390/molecules23020286.

Chloro-1,4-dimethyl-9H-carbazole Derivatives Displaying Anti-HIV Activity

Carmela Saturnino  1 , Fedora Grande  2 , Stefano Aquaro  3 , Anna Caruso  4 , Domenico Iacopetta  5 , Maria Grazia Bonomo  6 , Pasquale Longo  7 , Dominique Schols  8 , Maria Stefania Sinicropi  9
Affiliations

Chloro-1,4-dimethyl-9H-carbazole Derivatives Displaying Anti-HIV Activity

Carmela Saturnino et al. Molecules. .

Abstract

Background: Despite the progress achieved by anti-retroviral drug research in the last decades, the discovery of novel compounds endowed with selective antiviral activity and reduced side effects is still a necessity. At present, the most urgent requirement includes the improvement of HIV (Human Immunodeficiency Virus) prevention and sexual transmission and the development of new drugs to treat the chronic lifelong infection.

Methods: Six chloro-1,4-dimethyl-9H-carbazoles (2a,b-4a,b) have been prepared following opportunely modified known chemical procedures and tested in luciferase and Escherichia coli β-galactosidase expressing CD4⁺, CXCR4⁺, CCR5⁺ TZM-bl cells.

Results and conclusion: a preliminary biological investigation on the synthesized small series of chloro-1,4-dimethyl-9H-carbazoles has been carried out. Among all tested compounds, a nitro-derivative (3b) showed the most interesting profile representing a suitable lead for the development of novel anti-HIV drugs.

Keywords: HIV; antiviral agents; carbazole derivatives.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Synthesis of chloro-1,4-dimethyl-9H-carbazoles. Reagents and conditions: (i) acetonylacetone, p-TSA, ethanol, 6 h, reflux; (ii) HNO3, acetic anhydride, CH2Cl2, 5 min, −15 °C; (iii) CH3CO2H/HCl, SnCl2, DMF, 3 h, 100 °C.
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