trans-3,4-bis(3-indolyl)-2,5-pyrrolidinedione | 137467-07-3

• 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: trans-3,4-bis(3-indolyl)-2,5-pyrrolidinedione
• 英文别名: (3R,4R)-3,4-bis(1H-indol-3-yl)pyrrolidine-2,5-dione
• CAS: 137467-07-3
• 化学式: C₂₀H₁₅N₃O₂
• 分子量: 329.358
• InChiKey: QBMMMCZNMCDPBJ-ROUUACIJSA-N

物化性质

• 沸点：
  686.7±55.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚 、 3-溴-1H-吡咯-2,5-二酮 在 甲基氯化镁 作用下， 生成 trans-3,4-bis(3-indolyl)-2,5-pyrrolidinedione
  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

• INDOLE DERIVATIVES WITH ANTIVIRAL ACTIVITY
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0630241A1

  公开（公告）日：1994-12-28
• [EN] INDOLE DERIVATIVES WITH ANTIVIRAL ACTIVITY
  申请人：——

  公开号：WO1993018765A1

  公开（公告）日：1993-09-30

  [EN] The present invention relates to certain indole derivatives, salts, esters and physiologically functional derivatives thereof, to their use in medical therapy and in particular to their use for the manufacture of a medicament for the treatment or prophylaxis of at least one viral infection, for example, herpes virus, retrovirus, hepatitis B virus, coxsackie virus and hepatitis C virus infections.
  [FR] La présente invention se rapporte à certains dérivés d'indole et à des sels, des esters et des dérivés à activité physiologique de ces composés; l'invention se rapporte également à leur utilisation thérapeutique et en particulier à leur utilisation dans la fabrication d'un médicament destiné au traitement ou à la prophylaxie d'au moins une infection virale telle que l'infection par le virus de l'herpès, un rétrovirus, le virus de l'hépatite B, le virus coxsackie et le virus de l'hépatite C.
• Inhibitors of protein kinase C. 1. 2,3-bisarylmaleimides
  作者：Peter D. Davis、Christopher H. Hill、Geoffrey Lawton、John S. Nixon、Sandra E. Wilkinson、Steven A. Hurst、Elizabeth Keech、Susan E. Turner

  DOI：10.1021/jm00079a024

  日期：1992.1

  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).