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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) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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