-Drug Synthesis Database

【结构式】

【药物名称】

【化学名称】N-[2-[4-(Methylsulfonamido)phenyl]ethyl]-N-[2-(naphthalen-1-yloxy)ethyl]acetamide

【CA登记号】

【分子式】C₂₃H₂₆N₂O₄S

【分子量】426.53867

【开发单位】China Pharmaceutical University (Originator), Chinese Academy of Sciences (Originator)

【药理作用】Antiarrhythmic Drugs, CARDIOVASCULAR DRUGS, Potassium Channel Blockers

合成路线1

Alkylation of 1-napthol (I) with 1,2-dibromoethane provides the (naphthyloxy)ethyl bromide (II), which is condensed with p-nitrophenethylamine (III) to afford the secondary amine (IV). After acetylation of amine (IV) to produce acetamide (V), the nitro group of (V) is reduced by means of iron and HCl, yielding aniline (VI). Finally, acylation of the amino group of (VI) with methanesulfonyl chloride furnishes the target sulfonamide.

参考文献中间体

【1】 Liu, H.; et al.; New p-methylsufonamido phenylamine analogues as class III antiarrhythmic agents: Design, synthesis, biological assay, and 3D-QSAR analysis. J Med Chem 2002, 45, 14, 2953.

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)	22935	alpha-naphthol; 1-naphthol	90-15-3	C₁₀H₈O	详情	详情
(II)	57707	2-bromoethyl 1-naphthyl ether; 1-(2-bromoethoxy)naphthalene		C₁₂H₁₁BrO	详情	详情
(III)	26560	4-nitrophenethylamine	24954-67-4	C₈H₁₀N₂O₂	详情	详情
(IV)	57708	2-(1-naphthyloxy)-N-(4-nitrophenethyl)-1-ethanamine; N-[2-(1-naphthyloxy)ethyl]-N-(4-nitrophenethyl)amine		C₂₀H₂₀N₂O₃	详情	详情
(V)	57709	N-[2-(1-naphthyloxy)ethyl]-N-(4-nitrophenethyl)acetamide		C₂₂H₂₂N₂O₄	详情	详情
(VI)	57710	N-(4-aminophenethyl)-N-[2-(1-naphthyloxy)ethyl]acetamide		C₂₂H₂₄N₂O₂	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(2)