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【结 构 式】

【药物名称】

【化学名称】N-[1(S)-(5-Methyl-4-oxo-4H-thieno[2,3-d][1,3]oxazin-2-yl)ethyl]-3-phenyl-2(E)-propenamide

【CA登记号】194352-21-1

【 分 子 式 】C18H16N2O3S

【 分 子 量 】340.40382

【开发单位】GlaxoSmithKline (Originator)

【药理作用】ANTIINFECTIVE THERAPY, Antiviral Drugs, Protease Inhibitors

合成路线1

The coupling of 2-amino-4-methylthiophene-3-carboxylic acid ethyl ester (I) with N-(tert-butoxycarbonyl)-L-alanine (II) by means of isobutyl chloroformate and NMM, followed by cyclization with triphenylphosphine in CCl4 gives the thieno-oxazinone (III), which is deprotected with TFA yielding (IV) with a free amino group that is acylated with cinnamic acid by means of DEC and DIEA.

1 Tew, D.G.; Pinto, I.L.S.M.; Jarvest, R.L.; Jennings, L.J.; Dabrowski, C.E.; Fernandez, A.V.; Lavery, P.; Inhibition of herpes proteases and antiviral activity of 2-substituted thieno[2,3-d]oxazinones. Bioorg Med Chem Lett 1999, 9, 3, 443.
2 Jarvest, R.L.; Jennings, L.J.A.; Pinto, I.L. (SmithKline Beecham plc); Thienoxazinone derivs. useful as antiviral agents. WO 9727200 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 29512 ethyl 2-amino-4-methyl-3-thiophenecarboxylate 43088-42-2 C8H11NO2S 详情 详情
(II) 26450 Boc-L-Alanine;(S)-2-((tert-butoxycarbonyl)amino)propanoic acid;N-Boc-L-alanine; (2S)-2-[(tert-butoxycarbonyl)amino]propionic acid 15761-38-3 C8H15NO4 详情 详情
(III) 28659 tert-butyl (1S)-1-(5-methyl-4-oxo-4H-thieno[2,3-d][1,3]oxazin-2-yl)ethylcarbamate C14H18N2O4S 详情 详情
(IV) 28660 2-[(1S)-1-aminoethyl]-5-methyl-4H-thieno[2,3-d][1,3]oxazin-4-one C9H10N2O2S 详情 详情
(V) 10449 (Z)-3-Phenyl-2-propenoic acid 621-82-9 C9H8O2 详情 详情
Extended Information