-Drug Synthesis Database

【结构式】

【药物名称】

【化学名称】3-[2-(6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]-2-[4-(dimethylamino)phenyl]quinazolin-4(3H)-one

【CA登记号】

【分子式】C₂₉H₃₂N₄O₃

【分子量】484.60339

【开发单位】Xenova (Originator)

【药理作用】Modulators of the Therapeutic Activity of Antineoplastic Agents, Multidrug Resistance Modulators, ONCOLYTIC DRUGS, MRP-1 Inhibitors, P-Glycoprotein (MDR-1) Inhibitors

合成路线1 合成路线2

合成路线1

The title compound can be synthesized by two routes. Condensation of anthranilic acid (I) with acid chloride (II) provides benzooxazinone (III). Refluxing of (III) with amine (IV) in the presence of p-toluenesulfonic acid yields a mixture of the target quinazolinone and the uncyclized diamide (V), which can be cyclized to the title compound by heating in H2SO4/HOAc.

参考文献中间体

【1】 Wang, S.; et al.; Studies on quinazolinones as dual inhibitors of Pgp and MRP1 in multidrug resistance. Bioorg Med Chem Lett 2002, 12, 4, 571.

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)	11661	2-Aminobenzoic acid;Anthranilic acid; o-Aminobenzoic acid	118-92-3	C₇H₇NO₂	详情	详情
(II)	39988	4-(dimethylamino)benzoyl chloride	4755-50-4	C₉H₁₀ClNO	详情	详情
(III)	57723	2-[4-(dimethylamino)phenyl]-4H-3,1-benzoxazin-4-one		C₁₆H₁₄N₂O₂	详情	详情
(IV)	57724	2-[6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]-1-ethanamine; 2-[6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]ethylamine		C₁₃H₂₀N₂O₂	详情	详情
(V)	57725	N-{2-[6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]ethyl}-2-{[4-(dimethylamino)benzoyl]amino}benzamide		C₂₉H₃₄N₄O₄	详情	详情

合成路线2

The anthranilic amide (I) is converted to the corresponding iminophosphorane (II) by treatment with triphenylphosphine, hexachloroethane and triethylamine. Subsequent condensation of (II) with acid chloride (III) gives rise to the desired quinazolinone.

参考文献中间体

【1】 Wang, S.; et al.; Studies on quinazolinones as dual inhibitors of Pgp and MRP1 in multidrug resistance. Bioorg Med Chem Lett 2002, 12, 4, 571.

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)	57726	2-amino-N-{2-[6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]ethyl}benzamide		C₂₀H₂₅N₃O₃	详情	详情
(II)	57727	N-{2-[6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]ethyl}-2-[(triphenylphosphoranylidene)amino]benzamide		C₃₈H₃₈N₃O₃P	详情	详情
(III)	39988	4-(dimethylamino)benzoyl chloride	4755-50-4	C₉H₁₀ClNO	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)