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Synthesis and Anti-Human Immunodeficiency Virus Type 1 Activity of (E)-N-Phenylstyryl-N-alkylacetamide Derivatives
- Source :
- Molecules, Vol 14, Iss 9, Pp 3176-3186 (2009), Molecules, Volume 14, Issue 9, Pages 3176-3186
- Publication Year :
- 2009
- Publisher :
- MDPI AG, 2009.
-
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.
- Subjects :
- synthesis
Stereochemistry
Anti-HIV Agents
Cell
Human immunodeficiency virus (HIV)
Pharmaceutical Science
(E)-N-phenylstyryl-N-alkylacetamides
medicine.disease_cause
Article
Analytical Chemistry
Styrenes
lcsh:QD241-441
lcsh:Organic chemistry
Drug Discovery
Acetamides
reverse transcriptase
medicine
Physical and Theoretical Chemistry
anti-HIV-1 activity
biology
Chemistry
Organic Chemistry
Reverse transcriptase
Enzyme assay
medicine.anatomical_structure
Chemistry (miscellaneous)
biology.protein
HIV-1
Molecular Medicine
Subjects
Details
- Language :
- English
- ISSN :
- 14203049
- Volume :
- 14
- Issue :
- 9
- Database :
- OpenAIRE
- Journal :
- Molecules
- Accession number :
- edsair.doi.dedup.....708c65b99cb15f19963b4e517b87aa23