9-acridinyl phenyl ether; 9-phenoxyacridine -Drug Synthesis Database

【结构式】

【分子编号】46458

【品名】9-acridinyl phenyl ether; 9-phenoxyacridine

【CA登记号】

【分子式】C₁₉H₁₃NO

【分子量】271.31836

【元素组成】C 84.11% H 4.83% N 5.16% O 5.9%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(VI)

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.

参考文献中间体

合成目标

【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

Extended Information