-药物合成数据库

【药物名称】

化学结构式(Chemical Structure):

参考文献No.	538850
标题:	Synthesis and evaluation of new sulfur-containing L-arginine-derived inhibitors of nitric oxide synthase
作者:	Ichimori, K.; Stuehr, D.J.; Atkinson, R.N.; King, S.B.
来源:	J Med Chem 1999,42(10),1842

合成路线图解说明: The fully protection of Nomega-(benzyloxycarbonyl)-L-ornithine (I) by usual methods gives Nomega-(benzyloxycarbonyl)-Nalpha-(tert-butoxycarbonyl)-L-ornithine tert-butyl ester (II), which is selectively deprotected at the omega amino group with H2 over Pd/C yielding the ornithine (III). The reaction of (III) with thiophosgene affords the isothiocyanate (IV), which is treated with hydrazine to afford the aminothiourea (V). Finally, this compound is deprotected with 4M HCl.

合成路线图解说明: The fully protection of Nomega-(benzyloxycarbonyl)-L-ornithine (I) by usual methods gives Nomega-(benzyloxycarbonyl)-Nalpha-(tert-butoxycarbonyl)-L-ornithine tert-butyl ester (II), which is selectively deprotected at the omega amino group with H2 over Pd/C yielding the ornithine (III). The reaction of (III) with thiophosgene affords the isothiocyanate (IV), which is treated with hydroxylamine to afford the hydroxythiourea (V). The methylation of (V) with methyl iodide and NaH affords the S-methyl derivative (VI), which is finally deprotected with 4M HCl.

合成路线图解说明: The fully protection of Nomega-(benzyloxycarbonyl)-L-ornithine (I) by usual methods gives Nomega-(benzyloxycarbonyl)-Nalpha-(tert-butoxycarbonyl)-L-ornithine tert-butyl ester (II), which is selectively deprotected at the omega amino group with H2 over Pd/C yielding the ornithine (III). The reaction of (III) with thiophosgene affords the isothiocyanate (IV), which is treated with hydrazine to afford the aminothiourea (V). The methylation of (V) with methyl iodide and NaH affords the S-methyl derivative (VI), which is finally deprotected with 4M HCl.