|
【结 构 式】 
|
【药物名称】Neo-acridine, Neomycin-acridine 【化学名称】O-2,6-Diamino-2,6-dideoxy-alpha-D-glucopyranosyl-(1--4)-O-[O-2,6-diamino-2,6-dideoxy-beta-L-idopyranosyl-(1--3)[5-[2-(acridin-9-ylamino)ethylsulfanyl]-5-deoxy-beta-D-ribofuranosyl-(1--5)]-2-deoxy-D-streptamine 【CA登记号】 【 分 子 式 】C38H58N8O12S 【 分 子 量 】850.99636 |
【开发单位】University of California, San Diego (Originator) 【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY |
合成路线1
Neomycin B (I) was protected with Boc2O to afford (II), which was then converted to sulfonate (III) upon treatment with 2,4,6-triisopropylbenzenesulfonyl chloride and pyridine. Displacement of the sulfonate group with 2-mercaptoethylamine (IV) produced the (aminoethyl)thioether (V). This was then condensed with 9-phenoxyacrydine (VI) to furnish, after acid deprotection of the Boc groups, the title neomycin-acridine conjugate.
| 【1】 Kirk, S.R.; et al.; Neomycin - Acridine conjugate: A potent inhibitor of Rev-RRE binding. J Am Chem Soc 2000, 122, 5, 980. |
| 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) | 46454 | (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[((1R,2R,3S,4R,6S)-4,6-diamino-2-[[(3R,4S,5R)-4-[[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxytetrahydro-2H-pyran-2-yl]oxy]-3-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]oxy]-3-hydroxycyclohexyl | C23H46N6O13 | 详情 | 详情 | |
| (II) | 46455 | tert-butyl [(2R,3S,4R,5R,6R)-6-[((1R,2R,3S,4R,6S)-4,6-bis[(tert-butoxycarbonyl)amino]-2-[[(3R,4S,5R)-4-[((2R,3R,4R,5S,6S)-3-[(tert-butoxycarbonyl)amino]-6-[[(tert-butoxycarbonyl)amino]methyl]-4,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy]-3-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]oxy]-3-hydroxycyclohexyl)oxy]-5-[(tert-butoxycarbonyl)amino]-3,4-dihydroxytetrahydro-2H-pyran-2-yl]methylcarbamate | C53H94N6O25 | 详情 | 详情 | |
| (III) | 46456 | [(2R,3S,4R)-5-([(1R,2R,3S,5R,6S)-3,5-bis[(tert-butoxycarbonyl)amino]-2-[((2R,3R,4R,5S,6R)-3-[(tert-butoxycarbonyl)amino]-6-[[(tert-butoxycarbonyl)amino]methyl]-4,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy]-6-hydroxycyclohexyl]oxy)-3-[((2R,3R,4R,5S,6S)-3-[(tert-butoxycarbonyl)amino]-6-[[(tert-butoxycarbonyl)amino]methyl]-4,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy]-4-hydroxytetrahydro-2-furanyl]methyl 2,4,6-triisopropylbenzenesulfonate | C68H116N6O27S | 详情 | 详情 | |
| (IV) | 13186 | 2-Aminoethanethiol; 2-Amino-1-ethanethiol; 2-Aminoethylhydrosulfide; Cysteamine | 60-23-1 | C2H7NS | 详情 | 详情 |
| (V) | 46457 | tert-butyl [(2S,3S,4R,5R,6R)-6-[[(2S,3S,4R)-2-[[(2-aminoethyl)sulfanyl]methyl]-5-([(1R,2R,3S,5R,6S)-3,5-bis[(tert-butoxycarbonyl)amino]-2-[((2R,3R,4R,5S,6R)-3-[(tert-butoxycarbonyl)amino]-6-[[(tert-butoxycarbonyl)amino]methyl]-4,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy]-6-hydroxycyclohexyl]oxy)-4-hydroxytetrahydro-3-furanyl]oxy]-5-[(tert-butoxycarbonyl)amino]-3,4-dihydroxytetrahydro-2H-pyran-2-yl]methylcarbamate | C55H99N7O24S | 详情 | 详情 | |
| (VI) | 46458 | 9-acridinyl phenyl ether; 9-phenoxyacridine | C19H13NO | 详情 | 详情 |