-Drug Synthesis Database

【结构式】

【药物名称】

【化学名称】1-Benzyl-3-phenyl-3,4-dihydroquinolin-2(1H)-one

【CA登记号】231289-46-6

【分子式】C₂₂H₁₉NO

【分子量】313.40283

【开发单位】Chonnam National University (Originator)

【药理作用】ONCOLYTIC DRUGS

合成路线1

Condensation of 2-nitrobenzaldehyde (I) with methyl phenylacetate (II) in the presence of lithium diisopropylamide in cold THF provided hydroxyester (III). Reduction of the nitro group of (III) with concomitant cyclization by hydrogenation over Pd/C in EtOAc produced the dihydroquinolinone (IV). Further hydrogenolysis of the hydroxyl group of (IV) over Pd/C in AcOH gave (V), which was finally alkylated with benzyl bromide and NaH to yield the N-benzylquinolinone.

参考文献中间体

【1】 Cho, W.-J.; Lee, J.Y.; Chung, B.-H.; Kim, T.S.; Choi, B.-G.; Cheon, S.H.; Studies on the synthesis and in vitro antitumor activity of the isoquinolone derivatives. Arch Pharmacal Res 1999, 22, 2, 179.

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)	11370	2-Nitrobenzaldehyde	552-89-6	C₇H₅NO₃	详情	详情
(II)	32831	methyl 2-phenylacetate	101-41-7	C₉H₁₀O₂	详情	详情
(III)	32832	methyl 3-hydroxy-3-(2-nitrophenyl)-2-phenylpropanoate		C₁₆H₁₅NO₅	详情	详情
(IV)	32833	4-hydroxy-3-phenyl-3,4-dihydro-2(1H)-quinolinone		C₁₅H₁₃NO₂	详情	详情
(V)	32834	3-phenyl-3,4-dihydro-2(1H)-quinolinone		C₁₅H₁₃NO	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)