3-(1-methyl-3-indolyl)-4-(2-naphthyl)-1H-pyrrole-2,5-dione | 137467-10-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(1-methyl-3-indolyl)-4-(2-naphthyl)-1H-pyrrole-2,5-dione
• 英文别名: 3-(1-methyl-1H-indol-3-yl)-4-(1-naphthalenyl)-1H-pyrrole-2,5-dione；(Arylindolyl)maleimide deriv. 20；3-(1-methylindol-3-yl)-4-naphthalen-2-ylpyrrole-2,5-dione
• CAS: 137467-10-8
• 化学式: C₂₃H₁₆N₂O₂
• 分子量: 352.392
• InChiKey: URVKCDCCZPNJLS-UHFFFAOYSA-N

物化性质

• 沸点：
  633.4±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  51.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-methylindole-3-glyoxylyl chloride 在 ammonium hydroxide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 3-(1-methyl-3-indolyl)-4-(2-naphthyl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Inhibitors of protein kinase C. 1. 2,3-bisarylmaleimides

  摘要：

  The design and synthesis of a series of novel inhibitors of protein kinase C (PKC) is described. These 2,3-bisarylznaleimides were derived from the structural lead provided by the indolocarbazoles, staurosporine and K252a. Optimum activity required the imide NH, both carbonyl groups, and the olefinic bond of the maleimide ring. 2,3-Bisindolylmaleimides were the most active, and the potency of these was improved by a chloro substituent at the 5-position of one indole ring (compound 28, IC50 0.11-mu-M). In a series of (phenylindolyl)maleimides, nitro compound 74 was most active (IC50 0.67-mu-M). Naphthalene 19 and benzothiophene 21 showed greater than 100-fold selectivity for inhibition of PKC over the closely related cAMP-dependent protein kinase (PKA).

  DOI：

  10.1021/jm00079a024

文献信息

• A Practical Method for the Synthesis of Indolylaryl- and Bisindolylmaleimides
  作者：Sudipta Roy、Sujata Roy、Gordon W. Gribble

  DOI：10.1021/ol0621203

  日期：2006.10.1

  Indolylaryl and indolylheteroarylmaleimides, including bisindolylmaleimides, are easily prepared by the reaction of N-methylindole-3-glyoxylamide with methyl aryl acetates in the presence of potassium tert-butoxide in THF.
• Substituierte Pyrrole
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0328026B1

  公开（公告）日：1993-04-28
• Process for the manufacture of substituted maleimides
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0540956B1

  公开（公告）日：1997-09-03
• US5057614A
  申请人：——

  公开号：US5057614A

  公开（公告）日：1991-10-15
• US5399712A
  申请人：——

  公开号：US5399712A

  公开（公告）日：1995-03-21