Synthesis and Anti-Human Immunodeficiency Virus Type 1 Activity of (E)-N-Phenylstyryl-N-alkylacetamide Derivatives
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
Entry | R1 | R2 | RT inhibition (%)b | IC50c (μM) | EC50d (μM) | CC50e (μM) | SIf (CC50/EC50) |
---|---|---|---|---|---|---|---|
5a | 3-Br | methyl | 45.42 | ND | 128 ± 20 | 409 ± 106 | 3.2 |
5b | 4-Br | methyl | 16.59 | ND | ND | ND | ND |
5c | 2-Br | methyl | 85.27 | 339 ± 107 | 60 ±10 | >789 | >13.2 |
5d | 2-Br | ethyl | 46.37 | ND | 48 ± 8 | 358 ± 88 | 7.5 |
5e | 2-Br | allyl | 47.76 | ND | 75 ± 13 | 337 ± 154 | 4.5 |
5f | 2-Br | acetyl | 60.55 | 320 ± 22 | 8 ± 1 | 85 ± 17 | 10.6 |
5g | 2-Br | benzyl | 47.56 | ND | 9 ± 2 | 51 ± 13 | 5.7 |
5h | 2-Br | 2,6-difluoro-benzyl | 57.33 | 295 ± 9 | 29 ± 4 | 172 ± 73 | 5.9 |
5i | 2-Br | 3,5-difluoro-benzyl | 88.89 | 97 ± 13 | 4 ± 0.5 | 116 ± 13 | 29 |
5j | 2-Br | 2,6-dichloro-benzyl | 30.34 | ND | 49 ± 10 | 190 ± 36 | 3.9 |
5k | 2-Cl | methyl | 75.22 | 434 ± 44 | 96 ± 20 | 441 ± 18 | 4.6 |
5l | 2-Cl | ethyl | 59.10 | 521 ± 11 | 91 ± 15 | 424 ± 22 | 4.7 |
5m | 2-Cl | allyl | 29.95 | ND | 118 ± 28 | 536 ± 41 | 4.5 |
5n | 2-F | methyl | 61.69 | 477 ± 107 | 130 ± 33 | 664 ± 79 | 5.5 |
5o | 2-F | allyl | 38.51 | ND | 261 ± 40 | 538 ± 138 | 2.0 |
5p | 2-methyl | methyl | 79.80 | 487 ± 27 | 116 ± 11 | 609 ± 177 | 5.2 |
5q | 2-methyl | allyl | 40.30 | ND | 273 ± 43 | >930 | >3.4 |
5r | 2,4-dimethoxy | methyl | 69.45 | 373 ± 40 | 32 ± 7 | 256 ± 35 | 8.0 |
5s | 2,4-dimethoxy | ethyl | 34.73 | ND | 19 ± 3 | 112 ± 10 | 5.9 |
5t | 2,4-dimethoxy | allyl | 36.62 | ND | 55 ± 4 | 290 ± 79 | 5.3 |
AZTg | NDi | ND | 1.08×10-2 | >509 | >47130 | ||
PFAh | 96.46 | 5 | ND | ND | ND |
2.2. Biological activity
3. Experimental
3.1. General
3.2. Preparation of (E)-β-phenylnitroolefins 2
3.3. Preparation of (E)-N-phenylstyrylacetamides 3
3.4. General procedure for the preparation of (E)-N-phenylstyryl-N-alkylacetamides 5: Preparation of (E)-N-(3-bromostyryl)-N-methylacetamide (5a)
3.5. Biological activity assays
4. Conclusions
Acknowledgements
- Sample Availability: Samples of the compounds 5a–5t are available from the authors.
References and Notes
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© 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/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. https://doi.org/10.3390/molecules14093176
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. https://doi.org/10.3390/molecules14093176
Chicago/Turabian StyleCheng, Pi, Ji-Jun Chen, Ning Huang, Rui-Rui Wang, Yong-Tang Zheng, and Yi-Zeng Liang. 2009. "Synthesis and Anti-Human Immunodeficiency Virus Type 1 Activity of (E)-N-Phenylstyryl-N-alkylacetamide Derivatives" Molecules 14, no. 9: 3176-3186. https://doi.org/10.3390/molecules14093176