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【结 构 式】 
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【药物名称】AR-C70484XX 【化学名称】4-[3-[4-(Decyloxy)phenoxy]-2-oxopropoxy]benzoic acid 【CA登记号】 【 分 子 式 】C26H34O6 【 分 子 量 】442.55728 |
【开发单位】AstraZeneca (Originator) 【药理作用】Antiarthritic Drugs, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Phospholipase A2 Inhibitors |
合成路线1
Monoalkylation of hydroquinone (I) with decyl bromide (II) under basic conditions provided 4-(decyloxy)phenol (III), which was further condensed with epichlorohydrin (IV) in the presence of Cs2CO3 to yield the glycidyl ether (V). Ring opening of epoxide (V) with allyl 4-hydroxybenzoate (VI) furnished adduct (VII). Then, oxidation of the secondary alcohol (VII) using the Dess-Martin reagent afforded the keto ester (VIII), which upon deprotection with palladium tetrakis(triphenylphosphine) gave the target carboxylic acid.
| 【1】 Connolly, S.; Botterll, S.; Bennion, C.; et al.; Design and synthesis of a novel and potent series of inhibitors of cytosolic phospholipase A2 based on a 1,3-disubstituted propan-2-one skeleton. J Med Chem 2002, 45, 6, 1348. |
| 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) | 13163 | p-Dihydrobenzene; Hydroquinone | 123-31-9 | C6H6O2 | 详情 | 详情 |
| (II) | 58570 | 1-Bromodecane; 1-Decyl bromide; Decyl bromide; n-decyl bromide | 112-29-8 | C10H21Br | 详情 | 详情 |
| (III) | 58571 | 4-Decyloxyphenol | C16H26O2 | 详情 | 详情 | |
| (IV) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
| (V) | 58572 | 2-{[4-(decyloxy)phenoxy]methyl}oxirane; decyl 4-(2-oxiranylmethoxy)phenyl ether | C19H30O3 | 详情 | 详情 | |
| (VI) | 21022 | allyl 4-hydroxybenzoate | C10H10O3 | 详情 | 详情 | |
| (VII) | 58573 | allyl 4-{3-[4-(decyloxy)phenoxy]-2-hydroxypropoxy}benzoate | C29H40O6 | 详情 | 详情 | |
| (VIII) | 58574 | allyl 4-{3-[4-(decyloxy)phenoxy]-2-oxopropoxy}benzoate | C29H38O6 | 详情 | 详情 |