1-benzyl-3-(2-pyridinylmethylidenyl)indolin-2-one | 25791-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-benzyl-3-(2-pyridinylmethylidenyl)indolin-2-one
• 英文别名: 1-benzyl-3-pyridin-2-ylmethylene-1,3-dihydro-indol-2-one；1-benzyl-3-(2-pyridylmethylene)-2-indolinone；1-Benzyl-isatinyliden-3-(2-picolin)；1-Benzyl-3-(pyridin-2-ylmethylidene)indol-2-one
• CAS: 25791-28-0
• 化学式: C₂₁H₁₆N₂O
• 分子量: 312.371
• InChiKey: JTIJCYLXTMNCNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  吡啶-2-甲醛 、 1-苄基-3H-吲哚-2-酮 在 哌啶 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以81%的产率得到1-benzyl-3-(2-pyridinylmethylidenyl)indolin-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.