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Abandoned drugs
Atevirdine
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Atevirdine

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Atevirdine
Atevirdine structure.svg
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
  • InChI=1S/C21H25N5O2/c1-3-22-18-5-4-8-23-20(18)25-9-11-26(12-10-25)21(27)19-14-15-13-16(28-2)6-7-17(15)24-19/h4-8,13-14,22,24H,3,9-12H2,1-2H3 checkY
    Key: UCPOMLWZWRTIAA-UHFFFAOYSA-N checkY
  • InChI=1/C21H25N5O2/c1-3-22-18-5-4-8-23-20(18)25-9-11-26(12-10-25)21(27)19-14-15-13-16(28-2)6-7-17(15)24-19/h4-8,13-14,22,24H,3,9-12H2,1-2H3
    Key: UCPOMLWZWRTIAA-UHFFFAOYAK
  • O=C(N2CCN(c1ncccc1NCC)CC2)c4cc3cc(OC)ccc3[nH]4
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).
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Atevirdine is a non-nucleoside reverse transcriptase inhibitor that has been studied for the treatment of HIV.

Synthesis

Atevirdine synthesis:SAR:

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



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