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【结 构 式】 
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【药物名称】 【化学名称】5-[2-(Ethylsulfonyloxy)-1,3-dioxo-2,3-dihydro-1H-isoindol-5-ylamino]-5-oxopentanoic acid methyl ester 【CA登记号】 【 分 子 式 】C16H18N2O8S 【 分 子 量 】398.39446 |
【开发单位】State University of New Jersey (Originator), University of South Alabama (Originator) 【药理作用】Chronic Obstructive Pulmonary Diseases (COPD), Treatment of, RESPIRATORY DRUGS, Leukocyte Elastase Inhibitors |
合成路线1
Condensation of 4-nitrophthalic anhydride (I) with O-benzyl hydroxylamine in refluxing toluene produced phthalimide (II). Catalytic transfer hydrogenation employing cyclohexene in the presence of Pd/C yielded 4-amino-N-hydroxyphthalimide (III), which was condensed with ethanesulfonyl chloride to give sulfonate (IV). Finally, acylation with acid chloride (V) furnished the title compound.
| 【1】 Kerrigan, J.E.; et al.; 6-Acylamino-2-[(alkylsulfonyl)oxy]-1H-isoindole-1,3-dione mechanism-based inhibitors of human leukocyte elastase. Bioorg Med Chem Lett 2000, 10, 1, 27. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 14640 | O-benzylhydroxylamine; 1-[(aminooxy)methyl]benzene | 622-33-3 | C7H9NO | 详情 | 详情 | |
| (I) | 31028 | 5-nitro-2-benzofuran-1,3-dione | 5466-84-2 | C8H3NO5 | 详情 | 详情 |
| (II) | 38147 | 2-(benzyloxy)-5-nitro-1H-isoindole-1,3(2H)-dione | C15H10N2O5 | 详情 | 详情 | |
| (III) | 38148 | 5-amino-2-hydroxy-1H-isoindole-1,3(2H)-dione | C8H6N2O3 | 详情 | 详情 | |
| (IV) | 38149 | 5-amino-2-[(ethylsulfonyl)oxy]-1H-isoindole-1,3(2H)-dione | C10H10N2O5S | 详情 | 详情 | |
| (V) | 20650 | methyl 5-chloro-5-oxopentanoate; methyl-4-chloroformylbutyrate | 1501-26-4 | C6H9ClO3 | 详情 | 详情 |