1-(p-methyl-phenethyl)-isoindigo | 1198772-88-1

• 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-(p-methyl-phenethyl)-isoindigo
• 英文别名: 1-[2-(4-methylphenyl)ethyl]-3-(2-oxo-1H-indol-3-ylidene)indol-2-one
• CAS: 1198772-88-1
• 化学式: C₂₅H₂₀N₂O₂
• 分子量: 380.446
• InChiKey: ZWSPQUPCMHFGAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.41
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-吲哚酮 、 1-(p-methyl-phenethyl)-isatin 在 盐酸 作用下， 以 水 、 溶剂黄146 为溶剂， 200.0 ℃ 、400.01 kPa 条件下， 反应 0.5h， 以49%的产率得到1-(p-methyl-phenethyl)-isoindigo
  参考文献：
  名称：

  Synthesis and evaluation of functionalized isoindigos as antiproliferative agents

  摘要：

  A series of functionalized isoindigos structurally related to meisoindigo (1-methylisoindigo), a therapeutic agent used for the treatment of a form of leukemia, were synthesized and evaluated for antiproliferative activities on a panel of human cancer cells. Two promising compounds (1-phenpropylisoindigo and 1-(p-methoxy-phenethyl)-isoindigo) that were more potent than meisoindigo and comparable to 6-bromoindirubin-3'-oxime on leukemic K562 and liver HuH7 cells were identified. Structure-activity relationships showed the importance of keeping one of the lactam NH in an unsubstituted state. Substitution of the other lactam NH with aryl or arylalkyl side chains retained or improved activity in most instances. An intact exocyclic double bond was also essential, possibly to maintain planarity and rigidity of the iso-indigo scaffold. None of the compounds were found to inhibit CDK2 in an in vitro assay, in spite of reports linking the antiproliferative activities of meisoindigo and other isoindigos to CDK2 inhibition. Hence, these functionalized isoindigos disrupted cell growth and proliferation by other mechanistic pathways that did not involve CDK2 inhibition. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.008