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. 2009 Aug 26;14(9):3176-86.
doi: 10.3390/molecules14093176.

Synthesis and anti-human immunodeficiency virus type 1 activity of (E)-N-phenylstyryl-N-alkylacetamide derivatives

Pi Cheng  1 , Ji-Jun Chen, Ning Huang, Rui-Rui Wang, Yong-Tang Zheng, Yi-Zeng Liang
Affiliations

Synthesis and anti-human immunodeficiency virus type 1 activity of (E)-N-phenylstyryl-N-alkylacetamide derivatives

Pi Cheng et al. Molecules. .

Abstract

A series of (E)-N-phenylstyryl-N-alkylacetamides, 5, were synthesized by direct reduction-acetylation of beta-arylnitroolefins, followed by N-alkylation. The title compounds were characterized by (1)H-NMR, EIMS and IR analysis. All the synthesized compounds were assayed as HIV-1 non-nucleoside reverse transcriptase inhibitors. A SAR study revealed that when group R(1) in 5 was ortho-substituted, the resulting compounds showed better inhibitory activities against HIV-1 RT. Among the tested compounds, 5i (R(1) = 2-Br, R(2) = 3,5-difluorobenzyl) exhibited the highest enzyme activity, with a 88.89% inhibitory ratio against HIV-1 reverse transcriptase at the tested concentration. Further cell-based anti-HIV-1 assays showed that compound 5i exhibited a SI value of 29 with an EC(50) value of 4 microM in C8166 cells.

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Figures

Scheme 1
Scheme 1
Structure of hamigeroxalamic acid, (E)-N-phenylstyryl acetamide and (E)-N-phenylstyryl-N-alkylacetamide.
Scheme 2
Scheme 2
Synthetic route for (E)-N-phenylstyryl-N-alkylacetamides (5).
Figure 2
Figure 2
One-pot synthesis of N-phenylstyryl acetamides 3.
See this image and copyright information in PMC

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