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【结 构 式】 
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【药物名称】Adaphostin, NSC-680410 【化学名称】4-(2,5-Dihydroxybenzylamino)benzoic acid 1-adamantyl ester 【CA登记号】241127-58-2 【 分 子 式 】C24H27NO4 【 分 子 量 】393.48709 |
【开发单位】Mayo Clinic (Originator), National Cancer Institute (Originator) 【药理作用】Oncolytic Drugs, Abl Kinase Inhibitors, Angiogenesis Inhibitors, Apoptosis Inducers, Inhibitors of Signal Transduction Pathways |
合成路线1
1-Adamantanol (I) was esterified with 4-nitrobenzoyl chloride (II) in the presence of pyridine, yielding adamantanyl 4-nitrobenzoate (III). After catalytic hydrogenation of the nitro group of (III), the resultant aniline (IV) was condensed with 2,5-dihydroxybenzaldehyde (V) to afford the corresponding Schiff base (VI). Subsequent hydrogenation of the imine double bond of (VI) over Pd/C gave rise to the target amine.
| 【1】 Narayanan, V.L.; Sausville, E.A.; Kaur, G.; Varma, R.K. (US Department of Health & Human Services); Disubstd. lavendustin A analogs and pharmaceutical compsns. comprising the analogs. EP 1060160; WO 9943636 . |
| 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) | 52642 | 1-Adamantanol; 1-Hydroxyadamantane; Tricyclo[3.3.1.1]decan-1-ol | 768-95-6 | C10H16O | 详情 | 详情 |
| (II) | 18941 | p-nitrobenzoyl chloride; 4-nitrobenzoyl chloride | 122-04-3 | C7H4ClNO3 | 详情 | 详情 |
| (III) | 52643 | tricyclo[3.3.1.1~3,7~]dec-1-yl 4-nitrobenzoate | C17H19NO4 | 详情 | 详情 | |
| (IV) | 52644 | tricyclo[3.3.1.1~3,7~]dec-1-yl 4-aminobenzoate | C17H21NO2 | 详情 | 详情 | |
| (V) | 52645 | 5-Hydroxysalicylaldehyde; Gentisinaldehyde; 2,5-Dihydroxybenzaldehyde | 1194-98-5 | C7H6O3 | 详情 | 详情 |
| (VI) | 52646 | tricyclo[3.3.1.1~3,7~]dec-1-yl 4-{[(2,5-dihydroxyphenyl)methylidene]amino}benzoate | C24H25NO4 | 详情 | 详情 |