-药物合成数据库

【药物名称】

化学结构式(Chemical Structure):

参考文献No.	33903
标题:	Thienoxazinone derivs. useful as antiviral agents
作者:	Jarvest, R.L.; Jennings, L.J.A.; Pinto, I.L. (SmithKline Beecham plc)
来源:	WO 9727200

合成路线图解说明: 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.

合成路线图解说明: 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 3-(5-bromothien-2-yl)-2(E)-propenoic acid by means of DEC and DIEA.

合成路线图解说明: The cyclization of 2-amino-4-methylthiophene-3-carboxylic acid (I) with N-(tert-butoxycarbonyl)-L-alanine (II), by means of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (DEC) and HOBT in DMF gives the protected thienooxazinone (III), which is deprotected with trifluoroacetic acid in dichloro methane yielding 2-(1(S)-aminoethyl)-5-methyl-4H-thieno[2,3-d][1,3]oxazin-4-one (IV). Finally, this compound is acylated with 4-oxo-4-phenyl-2(E)-butenoic acid (VI) by means of DEC and diisopropylethylamine in DMF.

参考文献No.	488734
标题:	Inhibition of human cytomegalovirus protease by enedione derivatives of thieno[2,3-d]oxazinones through a novel dual acylation/alkylation mechanism
作者:	Pinto, I.L.; Jarvest, R.L.; Clarke, B.; Dabrowski, C.E.; Fenwick, A.; Gorczyca, M.M.; Jennings, L.J.; Lavery, P.; Sternberg, E.J.; Tew, D.G.; West, A.
来源:	Bioorg Med Chem Lett 1999,9(3),449

合成路线图解说明: The cyclization of 2-amino-4-methylthiophene-3-carboxylic acid (I) with N-(tert-butoxycarbonyl)-L-alanine (II), by means of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (DEC) and HOBT in DMF gives the protected thienooxazinone (III), which is deprotected with trifluoroacetic acid in dichloro methane yielding 2-(1(S)-aminoethyl)-5-methyl-4H-thieno[2,3-d][1,3]oxazin-4-one (IV). Finally, this compound is acylated with 4-oxo-4-phenyl-2(E)-butenoic acid (VI) by means of DEC and diisopropylethylamine in DMF.