Atevirdine

Atevirdine is a non-nucleoside reverse transcriptase inhibitor that has been studied for the treatment of HIV.^[1]

Atevirdine

Identifiers
IUPAC name [4-[3-(ethylamino)pyridin-2-yl]piperazin-1-yl]-(5-methoxy-1H-indol-2-yl)methanone
CAS Number	136816-75-6
PubChem CID	60848
DrugBank	DB12264
ChemSpider	54835
UNII	N24015WC6D
ChEMBL	ChEMBL280527
CompTox Dashboard (EPA)	DTXSID40159940
Chemical and physical data
Formula	C21H25N5O2
Molar mass	379.464 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCNC1=C(N=CC=C1)N2CCN(CC2)C(=O)C3=CC4=C(N3)C=CC(=C4)OC
InChI 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 Key:UCPOMLWZWRTIAA-UHFFFAOYSA-N

Synthesis

Atevirdine synthesis:^[2][3] SAR:^[4]

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

• Delavirdine