Synthesis and in vitro anti-HIV-1 evaluation of some N-arylsulfonyl-3-formylindoles

Authors

  • Zhiping Che Henan University of Science and Technology. College of Forestry. Department of Plant Protection. Laboratory of Pharmaceutical Design & Synthesis
  • Yuee Tian Henan University of Science and Technology. College of Forestry. Department of Plant Protection. Laboratory of Pharmaceutical Design & Synthesis
  • Shengming Liu Henan University of Science and Technology. College of Forestry. Department of Plant Protection. Laboratory of Pharmaceutical Design & Synthesis
  • Mei Hu Henan University of Science and Technology. College of Forestry. Department of Plant Protection. Laboratory of Pharmaceutical Design & Synthesis
  • Genqiang Chen Henan University of Science and Technology. College of Forestry. Department of Plant Protection. Laboratory of Pharmaceutical Design & Synthesis

DOI:

https://doi.org/10.1590/s2175-97902018000317044

Keywords:

N-Arylsulfonyl-3-formylindole/synthesis, Human immunodeficiency virus type-1/inhibitor

Abstract

As our ongoing work on research of anti-HIV-1 inhibitors, fifteen N-arylsulfonyl-3-formylindoles (3ao) were designed and prepared through two step synthetic route. Firstly, 3-formylindoles (2a-c) were synthesized via the Vilsmeier-Haack reaction. Subsequently, treatment of 2a-c with the appropriate arylsulfonyl chlorides led to the corresponding target compounds in excellent yields. All analogues were also preliminary evaluated in vitro for their inhibitory activity against HIV-1 replication. Among of all the reported analogues, three compounds 3c, 3g and 3i displayed significant anti-HIV-1 activity, with EC50 values of 9.57, 11.04 and 5.02 μM, and TI values of 31.89, 13.79 and 81.69, respectively. N-mnitrophenylsulfonyl-3-formylindole (3c) and N-m-nitrophenylsulfonyl-6-methyl-3-formylindole (3i) especially exhibited the best promising anti-HIV-1 activity. In addition, it demonstrated that insertion of a methyl group at the C-6 position of the indolyl ring and a nitro group at the meta position of the arylsulfonyl ring, as in compound 3i, resulted in both low cytotoxicity (CC50 = 410.41 μM) and good antiviral activity.

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Published

2018-11-29

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Section

Articles

How to Cite

Synthesis and in vitro anti-HIV-1 evaluation of some N-arylsulfonyl-3-formylindoles. (2018). Brazilian Journal of Pharmaceutical Sciences, 54(3), e17044. https://doi.org/10.1590/s2175-97902018000317044