Next Article in Journal
Previous Article in Journal
Molecules 2009, 14(9), 3176-3186; doi:10.3390/molecules14093176
Article

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

1,* , 2, 3, 3, 3 and 1
Received: 1 July 2009; in revised form: 30 July 2009 / Accepted: 26 August 2009 / Published: 26 August 2009
Download PDF [250 KB, uploaded 18 June 2014]
Abstract: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


MDPI and ACS Style

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.

AMA Style

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(9):3176-3186.

Chicago/Turabian Style

Cheng, Pi; Chen, Ji-Jun; Huang, Ning; Wang, Rui-Rui; Zheng, Yong-Tang; Liang, Yi-Zeng. 2009. "Synthesis and Anti-Human Immunodeficiency Virus Type 1 Activity of (E)-N-Phenylstyryl-N-alkylacetamide Derivatives." Molecules 14, no. 9: 3176-3186.



Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert