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【结 构 式】 
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【药物名称】 【化学名称】Nomega-(Thiocarbazoyl)-L-ornithine 【CA登记号】 【 分 子 式 】C6H14N4O2S 【 分 子 量 】206.26808 |
【开发单位】Lerner Research Institute (Originator), Wake Forest University (Originator) 【药理作用】Pharmacological Tools, Nitric Oxide Synthase Inhibitors |
合成路线1
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.
| 【1】 Ichimori, K.; Stuehr, D.J.; Synthesis and evaluation of new sulfur-containing L-arginine-derived inhibitors of nitric oxide synthase. J Med Chem 1999, 42, 10, 1842. |
| 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) | 30898 | (2S)-2-amino-5-[[(benzyloxy)carbonyl]amino]pentanoic acid | C13H18N2O4 | 详情 | 详情 | |
| (II) | 30899 | tert-butyl (2S)-5-[[(benzyloxy)carbonyl]amino]-2-[(tert-butoxycarbonyl)amino]pentanoate | C22H34N2O6 | 详情 | 详情 | |
| (III) | 30900 | tert-butyl (2S)-5-amino-2-[(tert-butoxycarbonyl)amino]pentanoate | C14H28N2O4 | 详情 | 详情 | |
| (IV) | 30901 | tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-isothiocyanatopentanoate | C15H26N2O4S | 详情 | 详情 | |
| (V) | 30904 | tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-[(hydrazinocarbothioyl)amino]pentanoate | C15H30N4O4S | 详情 | 详情 |