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【结 构 式】 
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【药物名称】 【化学名称】6-Amino-2-phenyl-1-(beta-D-ribofuranosyl)imidazo[4,5-e][1,3]diazepine-4,8(1H,5H)-dione 【CA登记号】 【 分 子 式 】C17H17N5O6 【 分 子 量 】387.35494 |
【开发单位】Nabi Biopharmaceuticals (Originator), University of Maryland (Originator), Utah State University (Originator) 【药理作用】ANTIINFECTIVE THERAPY, Antiviral Drugs |
合成路线1
Glycosylation of dimethyl 2-phenylimidazole-4,5-dicarboxylate (I) with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (II) in the presence of hexamethyldisilazane, chlorotrimethylsilane and trifluoromethanesulfonic acid leads to the imidazole ribofuranoside (III). Then, cyclization of the imidazoledicarboxylate (III) with guanidine (IV), and simultaneous alcoholysis of the ribose ester groups in the presence of methanolic NaOMe gives rise to the target imidazodiazepine ribofuranoside
| 【1】 Zhang, N.; Chen, H.-M.; Sood, R.; Kalicharran, K.; Fattom, A.I.; Naso, R.B.; Barnard, D.L.; Sidwell, R.W.; Hosmane, R.S.; In vitro inhibition of the measles virus by novel ring-expanded ('fat') nucleoside analogues containing the imidazo[4,5-e]diazepine ring system. Bioorg Med Chem Lett 2002, 12, 23, 3391. |
| 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) | 62724 | 4-ethyl 5-methyl 2-phenyl-1H-imidazole-4,5-dicarboxylate | C14H14N2O4 | 详情 | 详情 | |
| (II) | 62725 | [(2R,3R,4R)-5-(acetyloxy)-3,4-bis(benzoyloxy)tetrahydro-2-furanyl]methyl benzoate | C28H24O9 | 详情 | 详情 | |
| (III) | 62726 | 4-ethyl 5-methyl 1-{(2R,3R,4R,5R)-3,4-bis(benzoyloxy)-5-[(benzoyloxy)methyl]tetrahydro-2-furanyl}-2-phenyl-1H-imidazole-4,5-dicarboxylate | C40H34N2O11 | 详情 | 详情 | |
| (IV) | 14790 | Guanidine | 113-00-8 | CH5N3 | 详情 | 详情 |