1-(1-苯基乙基)靛红 | 125941-72-2

• 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
• 中文名称: 1-(1-苯基乙基)靛红
• 英文名称: 1-(1-phenylethyl)isatin
• 英文别名: 1-(1-phenylethyl)-1H-indole-2,3-dione；1H-Indole-2,3-dione, 1-(1-phenylethyl)-；1-(1-phenylethyl)indole-2,3-dione
• CAS: 125941-72-2
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: UBEPPALAFUEXBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1-苯基乙基)靛红 在 一水合肼 作用下， 反应 0.5h， 以88%的产率得到1-(1-phenylethyl)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：

  N-(1-methylbenzyl)indoline 在 叔丁基过氧化氢 、 copper diacetate 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 以85%的产率得到1-(1-苯基乙基)靛红
  参考文献：
  名称：

  一种靛红衍生物的制备方法

  摘要：

  本发明公开了一种靛红衍生物的制备方法，以N‑取代的二氢吲哚为原料，以叔丁基过氧化氢TBHP水溶液作为氧化剂，以醋酸铜Cu(OAc)2作为催化剂，将上述的原料、氧化剂、催化剂和溶剂混合后，在75℃～95℃的条件下反应5～30min，反应液冷却后经过洗涤、萃取分离、干燥、除去溶剂和纯化后得到靛红衍生物；优点在于该方法可一步实现N‑取代的二氢吲哚直接氧化为靛红衍生物的过程；反应操作简单，敞口加热即可；反应时间短，只需10分钟即可得到高产率的靛红化合物；其次反应使用的催化剂和氧化剂都非常廉价，反应成本低。当采用特定的反应条件组合时，产率最高可达88％。

  公开号：

  CN109810043B

文献信息

• Alkylation of isatins with trichloroacetimidates
  作者：Nilamber A. Mate、Rowan I. L. Meador、Bhaskar D. Joshi、John D. Chisholm

  DOI：10.1039/d2ob00127f

  日期：——

  N-Alkylation of isatins can be achieved utilizing trichloroacetimidate electrophiles and a Lewis acid catalyst. These reactions provide access to N-alkyl isatins, versatile scaffolds which are often employed in the synthesis of pharmaceutical lead structures as well as natural products. Secondary trichloroacetimidates that are precursors to stabilized carbocations provided excellent yields of the isatin

  使用三氯乙酰亚胺酯和路易斯酸催化剂可以实现靛红的N-烷基化。这些反应提供了获得N-烷基靛红、多功能支架的途径，这些支架通常用于合成药物先导结构以及天然产物。作为稳定碳正离子的前体的仲三氯乙酰亚胺酯提供了极好的产率的靛红产物。靛红对取代的耐受性很好，尽管观察到 C7 取代的反应性降低，这可能是由于空间效应。溶剂效应可用于在相似反应条件下促进O-烷基化。
• Oxindole compounds and their uses as therapeutic agents
  申请人：Chafeev Mikhail

  公开号：US20070105820A1

  公开（公告）日：2007-05-10

  This invention is directed to oxindole compounds that are useful for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain. Pharmaceutical compositions comprising the compounds and methods of using the compounds are also disclosed.

  本发明涉及氧化吲哚化合物，其对钠通道介导的疾病或病状，如疼痛的治疗和/或预防有用。还公开了包含该化合物的制药组合物和使用该化合物的方法。
• Katritzky, Alan R.; Fan, Wei-Qiang; Liang, De-Sheng, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1541 - 1546
  作者：Katritzky, Alan R.、Fan, Wei-Qiang、Liang, De-Sheng、Li, Qiao-Ling

  DOI：——

  日期：——
• KATRITZKY, ALAN R.;FAN, WEI-QIANG;LIANG, DE-SHENG;LI, QIAO-LING, J. HETEROCYCL. CHEM., 26,(1989) N, C. 1541-1545
  作者：KATRITZKY, ALAN R.、FAN, WEI-QIANG、LIANG, DE-SHENG、LI, QIAO-LING

  DOI：——

  日期：——
• OXINDOLE COMPOUNDS AND THEIR USES AS THERAPEUTIC AGENTS
  申请人：XENON PHARMACEUTICALS INC.

  公开号：EP1877378A2

  公开（公告）日：2008-01-16