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Molecules 2009, 14(9), 3176-3186; doi:10.3390/molecules14093176

Synthesis and Anti-Human Immunodeficiency Virus Type 1 Activity of (E)-N-Phenylstyryl-N-alkylacetamide Derivatives

1,* , 2, 3, 3, 3 and 1
1 School of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China 2 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, the Chinese Academy of Sciences, Kunming 650204, China 3 Laboratory of Molecular Immunopharmacology, Key Laboratory of Animal Models and Human Diseases Mechanisms, Kunming Institute of Zoology, the Chinese Academy of Sciences, Kunming 650223, China
* Author to whom correspondence should be addressed.
Received: 1 July 2009 / Revised: 30 July 2009 / Accepted: 26 August 2009 / Published: 26 August 2009
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A series of (E)-N-phenylstyryl-N-alkylacetamides, 5, were synthesized by direct reduction-acetylation of β-arylnitroolefins, followed by N-alkylation. The title compounds were characterized by 1H-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 R1 in 5 was ortho-substituted, the resulting compounds showed better inhibitory activities against HIV-1 RT. Among the tested compounds, 5i (R1 = 2-Br, R2 = 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 EC50 value of 4 μM in C8166 cells.
Keywords: (E)-N-phenylstyryl-N-alkylacetamides; synthesis; reverse transcriptase; anti-HIV-1 activity (E)-N-phenylstyryl-N-alkylacetamides; synthesis; reverse transcriptase; anti-HIV-1 activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Cheng, P.; Chen, J.-J.; Huang, N.; Wang, R.-R.; Zheng, Y.-T.; Liang, Y.-Z. Synthesis and Anti-Human Immunodeficiency Virus Type 1 Activity of (E)-N-Phenylstyryl-N-alkylacetamide Derivatives. Molecules 2009, 14, 3176-3186.

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