1-(萘-2-基甲基)二氢吲哚-2-酮 | 1029017-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(萘-2-基甲基)二氢吲哚-2-酮
• 英文名称: 1-(naphthalen-2-ylmethyl)indolin-2-one
• CAS: 1029017-04-6
• 化学式: C₁₉H₁₅NO
• 分子量: 273.334
• InChiKey: HJLHLKXHHVOSFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-吡啶甲醛 、 1-(萘-2-基甲基)二氢吲哚-2-酮 在 哌啶 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以80%的产率得到1-(2-naphthylmethyl)-3-(4-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
• 作为产物：
  描述：

  在 siliaflash-G₆₀ 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以202 mg的产率得到1-(萘-2-基甲基)二氢吲哚-2-酮
  参考文献：
  名称：

  Platinum-Catalyzed Oxoarylations of Ynamides with Nitrones

  摘要：

  A new platinum-catalyzed oxoarylation of ynamides with nitrones is reported. Cascade sequences for the synthesis of indolin-2-ones via NaBH3CN reduction in situ of the initially formed oxoarylation products are also developed.

  DOI：

  10.1021/ol302621z