Description
A pyrimidone that is uracil which is substituted at positions 1, 5 and 6 by ethoxymethyl, isopropyl, and benzyl groups, respectively. A non-nucleoside inhibitor of HIV-1 reverse transcriptase, emivirine was an unsuccessful experimental agent for the treatment of HIV.
Chemical properties
| Chemical formula | Net charge | Average mass |
|---|---|---|
| C17H22N2O3 | 0 | 302.36820 |
Nomenclature
| IUPAC | SMILES | InChI | InChIKey | Synonyms |
|---|---|---|---|---|
| 6-benzyl-1-(ethoxymethyl)-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione | CCOCn1c(Cc2ccccc2)c(C(C)C)c(=O)[nH]c1=O | InChI=1S/C17H22N2O3/c1-4-22-11-19-14(10-13-8-6-5-7-9-13)15(12(2)3)16(20)18-17(19)21/h5-9,12H,4,10-11H2,1-3H3,(H,18,20,21) | MLILORUFDVLTSP-UHFFFAOYSA-N |
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Citations
- Boudet, N, et al. 2006. Chemo- and regioselective functionalization of uracil derivatives. Applications to the synthesis of oxypurinol and emivirine. Organic Letters. 8(17).
- Kopp, F, et al. 2007. Functionalization of unprotected uracil derivatives using the halogen-magnesium exchange. Organic Letters. 9(9).
- Szczech, GM, et al. 1999. Safety assessment, in vitro and in vivo, and pharmacokinetics of emivirine, a potent and selective nonnucleoside reverse transcriptase inhibitor of human immunodeficiency virus type 1. Antimicrobial Agents and Chemotherapy. 44(1).