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| Names | |
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| Preferred IUPAC name {4-[3-(Ethylamino)pyridin-2-yl]piperazin-1-yl}(5-methoxy-1H-indol-2-yl)methanone | |
| Identifiers | |
3D model (JSmol) | |
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| Properties | |
| C21H25N5O2 | |
| Molar mass | 379.46 g/mol |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Atevirdine is anon-nucleoside reverse transcriptase inhibitor that has been studied for the treatment ofHIV.[1]
Preparation of the pyridylpiperazine moiety starts by aromatic displacement of chlorine from 2-chloro-3-nitropyridine by piperazine to give3. The secondary amine is then protected as its BOC derivative by reaction withdi-tert-butyl dicarbonate (Boc anhydride) to give4. The nitro group is then reduced bycatalytic hydrogenation. Reductive alkylation with acetaldehyde in the presence oflithium cyanoborohydride gives the corresponding N-ethyl derivative. Theprotecting group is then removed by reaction withTFA. Reaction of the resulting amine with the imidazolide derivative of 5-methoxy-3-indoleacetic acid produces the amide reverse transcriptase inhibitor, atevirdine.
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