2,3-dihydro-10-imidazo<1,2-b>isoquinolin-5(1H)-one | 28670-67-9

• 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: 2,3-dihydro-10-imidazo<1,2-b>isoquinolin-5(1H)-one
• 英文别名: N-phenyl-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-b]isoquinoline-10-carbothioamide；5-oxo-1,2,3,5-tetrahydro-imidazo[1,2-b]isoquinoline-10-carbothioic acid anilide；5-oxo-N-phenyl-2,3-dihydro-1H-imidazo[1,2-b]isoquinoline-10-carbothioamide
• CAS: 28670-67-9
• 化学式: C₁₈H₁₅N₃OS
• 分子量: 321.403
• InChiKey: MCDUSWVITUHFBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  76.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-10-imidazo<1,2-b>isoquinolin-5(1H)-one 在 氢氧化钾 、 双氧水 作用下， 以 乙醇 、 水 为溶剂， 反应 0.75h， 以45%的产率得到5-oxo-N-phenyl-1,2,3,5-tetrahydroimidazo[1,2-b]isoquinoline-10-carboxamide
  参考文献：
  名称：

  New potent imidazoisoquinolinone derivatives as anti-Trypanosoma cruzi agents: Biological evaluation and structure–activity relationships

  摘要：

  A series of novel benzoimidazo andN-aryl-5-oxo-imidazo[1,2-b] isoquinoline-10-carbothioamides was developed. All the compounds were evaluated for their in vitro action against the epimastigote form of Trypanosoma cruzi. Four of them showed higher activity than Nifurtimox. Their unspecific cytotoxicity was evaluated using HeLa and L6 cells, being non-toxic at concentrations at least 15 and 200 times higher than that of T. cruzi IC50. To gain insight into the mechanism of action, their DNA binding properties and reactivity with glutathione were studied, and QSAR study was performed. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.011
• 作为产物：
  描述：

  邻羧基苯乙酸 以 四氢呋喃 、 邻二氯苯 为溶剂， 反应 12.0h， 生成 2,3-dihydro-10-imidazo<1,2-b>isoquinolin-5(1H)-one
  参考文献：
  名称：

  稠合三轮车。具有异常烯胺特性的b-熔融1（2 H）-异喹啉酮的合成与反应†

  摘要：

  高邻苯酸（1与1,2-，1,3-，和1,4-二胺）经历反应，得到稠合1（2 ħ）异喹啉酮等2，4，13，和25，其显示出标记烯胺字符。它们在N或C末端受到亲电试剂的攻击。咪唑并异喹诺酮2的一些值得注意的反应是与马来酸和丙烯酸的反应，分别形成四环48和51。与丙酸5进行了有趣的反应，形成苯并咪唑并萘啶53。从2引出了同样有趣的行为在其与甲醛的反应中，除了预期的亚甲基桥连分子59之外，新型螺环衍生物60是通过假定的氮杂二烯中间体63的二聚作用形成的。

  DOI：

  10.1002/hlca.19880710110

文献信息

• NAGARAJAN, KUPPUSWAMY;RAO, VUNNAM R.;SHAH, RASHMI K.;SHENOY, SHARADA J.;F+, HELV. CHIM. ACTA, 71,(1988) N 1, 77-92
  作者：NAGARAJAN, KUPPUSWAMY、RAO, VUNNAM R.、SHAH, RASHMI K.、SHENOY, SHARADA J.、F+

  DOI：——

  日期：——
• New potent imidazoisoquinolinone derivatives as anti-Trypanosoma cruzi agents: Biological evaluation and structure–activity relationships
  作者：Mariela Bollini、Juan José Casal、Diego E. Alvarez、Lucía Boiani、Mercedes González、Hugo Cerecetto、Ana María Bruno

  DOI：10.1016/j.bmc.2009.01.011

  日期：2009.2

  A series of novel benzoimidazo andN-aryl-5-oxo-imidazo[1,2-b] isoquinoline-10-carbothioamides was developed. All the compounds were evaluated for their in vitro action against the epimastigote form of Trypanosoma cruzi. Four of them showed higher activity than Nifurtimox. Their unspecific cytotoxicity was evaluated using HeLa and L6 cells, being non-toxic at concentrations at least 15 and 200 times higher than that of T. cruzi IC50. To gain insight into the mechanism of action, their DNA binding properties and reactivity with glutathione were studied, and QSAR study was performed. (c) 2009 Elsevier Ltd. All rights reserved.
• Condensed Heterotricycles. Synthesis and Reactions ofb-Fused 1(2H)-Isoquinolinones with unusual enaminic properties
  作者：Kuppuswamy Nagarajan、Vunnam R. Rao、Rashmi K. Shah、Sharada J. Shenoy、Hans Fritz、Wilhelm J. Richter、Dieter Muller

  DOI：10.1002/hlca.19880710110

  日期：1988.2.3

  Homophthalic acid (1) undergoes reaction with 1,2-, 1,3-, and 1,4-diamines to give condensed 1(2H)-isoquinolinones like 2, 4, 13, and 25, which exhibit marked enamine character. These are attacked by electrophiles at the N or C terminus. Some notable reactions of imidazoisoquinolone 2 are those with maleic and acrylic acids to form the tetracycles 48 and 51, respectively. With propiolic acid, 5 underwent

  高邻苯酸（1与1,2-，1,3-，和1,4-二胺）经历反应，得到稠合1（2 ħ）异喹啉酮等2，4，13，和25，其显示出标记烯胺字符。它们在N或C末端受到亲电试剂的攻击。咪唑并异喹诺酮2的一些值得注意的反应是与马来酸和丙烯酸的反应，分别形成四环48和51。与丙酸5进行了有趣的反应，形成苯并咪唑并萘啶53。从2引出了同样有趣的行为在其与甲醛的反应中，除了预期的亚甲基桥连分子59之外，新型螺环衍生物60是通过假定的氮杂二烯中间体63的二聚作用形成的。