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【结 构 式】 
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【药物名称】CT-2584, Apra 【化学名称】1-[11-(Dodecylamino)-10-hydroxyundecyl]-3,7-dimethylxanthine 【CA登记号】160944-05-8 (racemate) 【 分 子 式 】C30H55N5O3 【 分 子 量 】533.80455 |
【开发单位】Cell Therapeutics (Orphan Drug), Cell Therapeutics (Originator) 【药理作用】ONCOLYTIC DRUGS, Prostate Cancer Therapy, Solid Tumors Therapy |
合成路线1
The alkylation of theobromine (I) with undecenyl mesylate (II) in the presence of NaH in DMSO afforded the 1-undecenyl xanthine (III). Dihydroxylation of the terminal double bond of (III) by means of N-methylmorpholine-N-oxide and a catalytic amount of potassium osmate gave diol (IV), which was further converted to bromo acetate (V) by treatment with a solution of HBr in AcOH. Methanolysis of the bromoester (V) with concomitant cyclization gave rise to epoxide (VI). Finally, epoxide opening upon heating with dodecylamine (VII) furnished the target amino alcohol.
| 【1】 Michnick, J.; Underiner, G.E.; Klein, J.P.; Rice, G.C.; Sunkara, P.S. (Cell Therapeutics, Inc.); Second messenger cell signaling inhibitors. CH 686830; EP 0719267; JP 1996508981; US 5470878; WO 9422863 . |
| 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) | 16651 | theobromine; 3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione | 83-67-0 | C7H8N4O2 | 详情 | 详情 |
| (II) | 50459 | 10-undecenyl methanesulfonate | C12H24O3S | 详情 | 详情 | |
| (III) | 50460 | 3,7-dimethyl-1-(10-undecenyl)-3,7-dihydro-1H-purine-2,6-dione | C18H28N4O2 | 详情 | 详情 | |
| (IV) | 50461 | 1-(10,11-dihydroxyundecyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione | C18H30N4O4 | 详情 | 详情 | |
| (V) | 50462 | 1-(bromomethyl)-10-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)decyl acetate | C20H31BrN4O4 | 详情 | 详情 | |
| (VI) | 50463 | 3,7-dimethyl-1-[9-(2-oxiranyl)nonyl]-3,7-dihydro-1H-purine-2,6-dione | C18H28N4O3 | 详情 | 详情 | |
| (VII) | 40735 | 1-dodecanamine; dodecylamine | 124-22-1 | C12H27N | 详情 | 详情 |