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【结 构 式】 
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【药物名称】 【化学名称】3-(2-Benzyl-10-hydroxy-5-oxo-2,3,4,5-tetrahydro-1H-1-benzopyran[4,3-c]pyridin-8-yl)butyric acid ethyl ester 【CA登记号】 【 分 子 式 】C25H27NO5 【 分 子 量 】421.49764 |
【开发单位】Kos Pharmaceuticals (Originator), University of Florida (Originator) 【药理作用】Antiglaucoma Agents, OCULAR MEDICATIONS, Ophthalmic Drugs |
合成路线1
Horner-Emmons condensation of 3',5'-di(benzyloxy)acetophenone (I) with triethyl phosphonoacetate yields the unsaturated ester (II). Catalytic double bond hydrogenation in (II), with simultaneous benzyl group hydrogenolysis, leads to the substituted resorcinol (III). This is then subjected to Pechmann cyclization with ethyl 1-benzyl-3-oxopiperidine-4-carboxylate (IV) in the presence of H2SO4 and POCl3 to provide the target benzopyranopyridine compound.
| 【1】 Buchwald, A.; et al.; Soft cannabinoid analogues as potential anti-glaucoma agents. Pharmazie 2002, 57, 2, 108. |
| 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) | 37920 | 1-[3,5-bis(benzyloxy)phenyl]-1-ethanone | 28924-21-2 | C22H20O3 | 详情 | 详情 |
| (II) | 58977 | ethyl (E)-3-[3,5-bis(benzyloxy)phenyl]-2-butenoate | C26H26O4 | 详情 | 详情 | |
| (III) | 58978 | ethyl 3-(3,5-dihydroxyphenyl)butanoate | C12H16O4 | 详情 | 详情 | |
| (IV) | 57371 | ethyl 1-benzyl-3-oxo-4-piperidinecarboxylate | C15H19NO3 | 详情 | 详情 |