methyl 7-(ethylphenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate | 1153594-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: methyl 7-(ethylphenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate
• 英文别名: methyl 7-(N-ethylanilino)-1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate
• CAS: 1153594-99-0
• 化学式: C₂₁H₂₀N₂O₄
• 分子量: 364.401
• InChiKey: KDSKRLOGTVNQBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  124-125.5 °C
• 沸点：
  559.1±50.0 °C(predicted)
• 密度：
  1.282±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  76.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylic acid methyl ester 、 N-乙基苯胺 在 cerium(III) chloride heptahydrate 作用下， 以 乙醇 为溶剂， 反应 47.0h， 以30%的产率得到methyl 7-(ethylphenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate
  参考文献：
  名称：

  Studies on quinones. Part 45: Novel 7-aminoisoquinoline-5,8-quinone derivatives with antitumor properties on cancer cell lines

  摘要：

  A variety of 7-aminoisoquinoline-5,8-quinone derivatives were prepared from 2,5-dihydroxyacetophenone, methyl aminocrotonate, and the corresponding amines, through a highly efficient three-step sequence. The members of this series were tested on normal human fibroblasts and on a panel of three human cancer cell lines and their redox properties were determined by cyclic voltammetry in acetonitrile. Both the cytotoxicity and antitumor activity of 7-phenylaminoisoquinoline-5,8-quinone derivatives showed correlation with their half wave potentials and lipophilicities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.013

文献信息

• Studies on quinones. Part 45: Novel 7-aminoisoquinoline-5,8-quinone derivatives with antitumor properties on cancer cell lines
  作者：Jaime A. Valderrama、J. Andrea Ibacache、Verónica Arancibia、Jaime Rodriguez、Cristina Theoduloz

  DOI：10.1016/j.bmc.2009.02.013

  日期：2009.4

  A variety of 7-aminoisoquinoline-5,8-quinone derivatives were prepared from 2,5-dihydroxyacetophenone, methyl aminocrotonate, and the corresponding amines, through a highly efficient three-step sequence. The members of this series were tested on normal human fibroblasts and on a panel of three human cancer cell lines and their redox properties were determined by cyclic voltammetry in acetonitrile. Both the cytotoxicity and antitumor activity of 7-phenylaminoisoquinoline-5,8-quinone derivatives showed correlation with their half wave potentials and lipophilicities. (C) 2009 Elsevier Ltd. All rights reserved.