Atevirdine

Atevirdine

Names
IUPAC name [4-[3-(Ethylamino)pyridin-2-yl]piperazin-1-yl]-(5-methoxy-1H-indol-2-yl)methanone
Identifiers
CAS Number	136816-75-6 N
ChEMBL	ChEMBL280527 Y
ChemSpider	54835 Y
Jmol 3D model	Interactive image
PubChem	60848
UNII	N24015WC6D Y
InChI 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 Y Key: UCPOMLWZWRTIAA-UHFFFAOYSA-N Y 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
SMILES O=C(N2CCN(c1ncccc1NCC)CC2)c4cc3cc(OC)ccc3n4
Properties
Chemical formula	C21H25N5O2
Molar mass	379.46 g/mol
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Ateviridine is 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. Reaaction of the resulting amine with the imidazolide derivative of 5-Methoxy-3-indoleacetic acid affords the amide reverse transcriptase inhibitor, atevirdine.

See also

• Delavirdine