• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【药物名称】

【化学名称】5-[2-(Diethylamino)ethylaminomethyl]-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one hydrochloride

【CA登记号】

【 分 子 式 】C25H31ClN2O3

【 分 子 量 】442.99042

【开发单位】NCSR Demokritos (Originator), University of Athens (Originator)

【药理作用】ONCOLYTIC DRUGS

合成路线1

Condensation of methyl 3,5-dihydroxybenzoate (I) with 3-chloro-3-methyl-1-butyne (II) in the presence of CuI, followed by thermal cyclization at 75 C, gives rise to a mixture of two regioisomeric chromenes (III) and (IV). After chromatographic separation, the desired isomer (III) is reduced with LiAlH4 to provide alcohol (V). Copper-catalyzed coupling of the phenolic chromene (V) with sodium 2-iodobenzoate (VI) leads to the diaryl ether (VII), which is further cyclized to the pyranoxanthenone (VIII) in the presence of trifluoroacetic anhydride. After basic hydrolysis of the trifluoroacetate ester (VIII), the resultant alcohol (IX) is converted to mesylate (X) by treatment with methanesulfonyl chloride and triethylamine. Finally, displacement of the mesylate group of (X) with N,N-diethyl ethylenediamine (XI) furnishes the title compound.

1 Kolokythas, G.; et al.; Design and synthesis of some new pyranoxanthenone aminoderivatives with cytotoxic activity. Bioorg Med Chem Lett 2002, 12, 11, 1443.
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) 25155 methyl 3,5-dihydroxybenzoate 2150-44-9 C8H8O4 详情 详情
(II) 22416 3-chloro-3-methyl-1-butyne 1111-97-3 C5H7Cl 详情 详情
(III) 57036 methyl 7-hydroxy-2,2-dimethyl-2H-chromene-5-carboxylate C13H14O4 详情 详情
(IV) 57037 methyl 5-hydroxy-2,2-dimethyl-2H-chromene-7-carboxylate C13H14O4 详情 详情
(V) 57039 5-(hydroxymethyl)-2,2-dimethyl-2H-chromen-7-ol C12H14O3 详情 详情
(VI) 57038 sodium 2-iodobenzoate C7H4INaO2 详情 详情
(VII) 57040 2-{[5-(hydroxymethyl)-2,2-dimethyl-2H-chromen-7-yl]oxy}benzoic acid C19H18O5 详情 详情
(VIII) 57041 (2,2-dimethyl-6-oxo-2H,6H-pyrano[3,2-b]xanthen-5-yl)methyl 2,2,2-trifluoroacetate C21H15F3O5 详情 详情
(IX) 57042 5-(hydroxymethyl)-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one C19H16O4 详情 详情
(X) 57043 (2,2-dimethyl-6-oxo-2H,6H-pyrano[3,2-b]xanthen-5-yl)methyl methanesulfonate C20H18O6S 详情 详情
(XI) 12420 N-(2-Aminoethyl)-N,N-diethylamine; N,N-Diethylethylene-diamine; N(1),N(1)-Diethyl-1,2-ethanediamine 100-36-7 C6H16N2 详情 详情
Extended Information