Chemistry:Atevirdine
| |
| Names | |
|---|---|
| Preferred IUPAC name
{4-[3-(Ethylamino)pyridin-2-yl]piperazin-1-yl}(5-methoxy-1H-indol-2-yl)methanone | |
| Identifiers | |
3D model (JSmol)
|
|
| ChEMBL | |
| ChemSpider | |
PubChem CID
|
|
| UNII | |
| |
| |
| Properties | |
| C21H25N5O2 | |
| Molar mass | 379.46 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
| |
| Infobox references | |
Atevirdine is a non-nucleoside reverse transcriptase inhibitor that has been studied for the treatment of HIV.[1]
Synthesis
Preparation of the pyridylpiperazine moiety starts by aromatic displacement of chlorine from 2-chloro-3-nitropyridine by piperazine to give 3. The secondary amine is then protected as its BOC derivative by reaction with di-tert-butyl dicarbonate (Boc anhydride) to give 4. The nitro group is then reduced by catalytic hydrogenation. Reductive alkylation with acetaldehyde in the presence of lithium cyanoborohydride gives the corresponding N-ethyl derivative. The protecting group is then removed by reaction with TFA. Reaction of the resulting amine with the imidazolide derivative of 5-methoxy-3-indoleacetic acid produces the amide reverse transcriptase inhibitor, atevirdine.
See also
References
- ↑ "Concentration-targeted phase I trials of atevirdine mesylate in patients with HIV infection: dosage requirements and pharmacokinetic studies. The ACTG 187 and 199 study teams". Antiviral Res. 45 (1): 47–58. January 2000. doi:10.1016/S0166-3542(99)00073-X. PMID 10774589.
- ↑ D. L. Romero, Drugs Future 19, 9 (1995).
- ↑ Romero, Donna Lee; Mark Allen Mitchell & Richard Charles Thomas et al., "Diaromatic substituted anti-AIDS compounds", WO patent 9109849, published 1991-07-11
- ↑ Romero, D. L. et al. (1994). "Discovery, Synthesis, and Bioactivity of Bis(heteroaryl)piperazines. 1. A Novel Class of Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors". Journal of Medicinal Chemistry 37 (7): 999–1014. doi:10.1021/jm00033a018. PMID 7512142.
 |  |
