(3Z)-1-(1-phenylethyl)-3-(quinolin-3-ylmethylidene)indol-2-one | 1029017-38-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (3Z)-1-(1-phenylethyl)-3-(quinolin-3-ylmethylidene)indol-2-one
• CAS: 1029017-38-6
• 化学式: C₂₆H₂₀N₂O
• 分子量: 376.458
• InChiKey: UPMCHNXPOQCNPQ-KQWNVCNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-喹啉甲醛 、 1-(1-phenylethyl)indolin-2-one 在 哌啶 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 (3Z)-1-(1-phenylethyl)-3-(quinolin-3-ylmethylidene)indol-2-one 、 (3E)-1-(1-phenylethyl)-3-(quinolin-3-ylmethylidene)indol-2-one
  参考文献：
  名称：

  Synthesis of 1-substituted 3-pyridinylmethylidenylindolin-2-ones and 1-substituted 3-quinolinylmethylidenylindolin-2-ones as the enhancers of ATRA-induced differentiation in HL-60 cells

  摘要：

  As part of our continuing search for potential differentiation agents, 1-benzyl-3-(4-pyridinylmethylidenyl)indolin-2-one (14) was selected as lead compound, and its new pyridinyl and quinolinyl analogs were synthesized and evaluated for differentiation-inducing activity toward HL-60 cells. Most of the tested compounds enhanced the ATRA-induced differentiation; among them, 1-(1-phenylethyl)-3-(3-quinolinylmethylidenyl)indolin-2-one (25) was the most promising one. The two isomers, 25Z and 25E; consisting 25 were found to have similar differentiation activity. The combination of 25 with all trans retinoic acid (ATRA) was found to induce complete differentiation of HL-60 cells and arrest the cells in the G0/G1 phase of the cell cycle. Beside its excellent differentiation activity, 25 also exhibited relatively low cytotoxicity toward normal cells. Therefore, compound 25 is recommended as a candidate for further development of novel enhancer of ATRA-induced differentiation in HL-60 cells. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.02.093

文献信息

• Synthesis of 1-substituted 3-pyridinylmethylidenylindolin-2-ones and 1-substituted 3-quinolinylmethylidenylindolin-2-ones as the enhancers of ATRA-induced differentiation in HL-60 cells
  作者：Chi-Ying Hung、Mei-Hua Hsu、Li-Jiau Huang、Chrong-Shiong Hwang、On Lee、Chen-Yi Wu、Chih-Hung Chen、Sheng-Chu Kuo

  DOI：10.1016/j.bmc.2008.02.093

  日期：2008.4

  As part of our continuing search for potential differentiation agents, 1-benzyl-3-(4-pyridinylmethylidenyl)indolin-2-one (14) was selected as lead compound, and its new pyridinyl and quinolinyl analogs were synthesized and evaluated for differentiation-inducing activity toward HL-60 cells. Most of the tested compounds enhanced the ATRA-induced differentiation; among them, 1-(1-phenylethyl)-3-(3-quinolinylmethylidenyl)indolin-2-one (25) was the most promising one. The two isomers, 25Z and 25E; consisting 25 were found to have similar differentiation activity. The combination of 25 with all trans retinoic acid (ATRA) was found to induce complete differentiation of HL-60 cells and arrest the cells in the G0/G1 phase of the cell cycle. Beside its excellent differentiation activity, 25 also exhibited relatively low cytotoxicity toward normal cells. Therefore, compound 25 is recommended as a candidate for further development of novel enhancer of ATRA-induced differentiation in HL-60 cells. (C) 2008 Published by Elsevier Ltd.