5-methoxy-1,2-naphthalenedione -Drug Synthesis Database

【结构式】

【分子编号】47913

【品名】5-methoxy-1,2-naphthalenedione

【CA登记号】

【分子式】C₁₁H₈O₃

【分子量】188.18272

【元素组成】C 70.21% H 4.28% O 25.51%

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：(II)

The oxidation of 5-methoxy-1-tetralone (I) with SeO2 gives 5-methoxy-1,2-naphthoquinone (II), which is cyclized with 2,3-diaminobenzoic acid (II) by means of HCl in refluxing ethanol to yield 4-methoxybenzo[a]phenazine-11-carboxylic acid (IV). Finally, this acid is converted into the target amide by its condensation with N1,N1,2(R)-trimethylethane-1,2-diamine (V) by means of CDI in DMF.

参考文献中间体

合成目标

【1】 Vicker, N.; Burgess, L.; Chuckowree, I.S.; et al.; Novel angular benzophenazines: Dual topoisomerase I and topoisomerase II inhibitors as potential anticancer agents. J Med Chem 2002, 45, 3, 721.
【2】 Vicker, N.; Folkes, A.J.; Wang, S.; Milton, J.; Denny, W.A. (Xenova Group plc); Benzo[a]phenazin-11-carboxamide derivs. and their use as joint inhibitors of topomerase I and II. WO 0146157 .

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)	18568	5-methoxy-3,4-dihydro-1(2H)-naphthalenone	33892-75-0	C₁₁H₁₂O₂	详情	详情
(II)	47913	5-methoxy-1,2-naphthalenedione		C₁₁H₈O₃	详情	详情
(III)	47914	2,3-diaminobenzoic acid		C₇H₈N₂O₂	详情	详情
(IV)	47915	4-methoxybenzo[a]phenazine-11-carboxylic acid		C₁₈H₁₂N₂O₃	详情	详情
(V)	47916	(2R)-N(1),N(1)-dimethyl-1,2-propanediamine; N-[(2R)-2-aminopropyl]-N,N-dimethylamine		C₅H₁₄N₂	详情	详情

Extended Information