2-(6-bromo-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide | 546102-48-1

• 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: 2-(6-bromo-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide
• 英文别名: 3-(6-bromo-1H-indol-3-yl)-4-(1H-indol-3-yl)pyrrole-2,5-dione
• CAS: 546102-48-1
• 化学式: C₂₀H₁₂BrN₃O₂
• 分子量: 406.238
• InChiKey: SOGWJGRXUBNIBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(6-bromo-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide 在 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 5.0h， 以79%的产率得到Cdk4抑制剂
  参考文献：
  名称：

  Synthesis, Structure−Activity Relationship, and Biological Studies of Indolocarbazoles as Potent Cyclin D1-CDK4 Inhibitors

  摘要：

  Novel substituted indolocarbazoles were synthesized, and their kinase inhibitory capability was evaluated in vitro. 6-Substituted indolocarbazoles 4 were found to be potent and selective D1/CDK4 inhibitors. 4d and 4h exhibited potent and ATP-competitive D1/CDK4 activities with IC50 values of 76 and 42 nM, respectively. Both compounds had high selectivity against the other kinases. These D1/CDK4 inhibitors inhibited tumor cell growth, arrested tumor cells at the G1 phase, and inhibited pRb phosphorylation.

  DOI：

  10.1021/jm0256169
• 作为产物：
  描述：

  吲哚-3-乙醛酸甲酯 、 6-Bromoindole-3-acetamide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 2-(6-bromo-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide
  参考文献：
  名称：

  Synthesis, Structure−Activity Relationship, and Biological Studies of Indolocarbazoles as Potent Cyclin D1-CDK4 Inhibitors

  摘要：

  Novel substituted indolocarbazoles were synthesized, and their kinase inhibitory capability was evaluated in vitro. 6-Substituted indolocarbazoles 4 were found to be potent and selective D1/CDK4 inhibitors. 4d and 4h exhibited potent and ATP-competitive D1/CDK4 activities with IC50 values of 76 and 42 nM, respectively. Both compounds had high selectivity against the other kinases. These D1/CDK4 inhibitors inhibited tumor cell growth, arrested tumor cells at the G1 phase, and inhibited pRb phosphorylation.

  DOI：

  10.1021/jm0256169

文献信息

• Maleinimid-Derivate und deren Verwendung als Arzneimittel
  申请人：GÖDECKE AKTIENGESELLSCHAFT

  公开号：EP0397060A2

  公开（公告）日：1990-11-14

  Die Erfindung betrifft neue Bis-(1H-indol-3-yl)maleinimid-­Derivate, Verfahren zu deren Herstellung, Arzneimittel enthaltend diese Verbindungen und deren Verwendung zur Behandlung von Herz- und Gefäßkrankheiten wie Thrombosen, Arteriosklerose, Hypertension, von Entzündungsprozessen, Allergien, Krebs und bestimmten degenerativen Schäden des Zentralnervensystems sowie von Krankheiten des Immunsystems und viraler Erkrankungen.

  本发明涉及新的双-(1H-吲哚-3-基)马来酰亚胺衍生物、其制备工艺、含有这些化合物的药物及其在治疗心血管疾病（如血栓形成、动脉硬化、高血压、炎症过程、过敏、癌症和某些中枢神经系统变性损伤）以及免疫系统疾病和病毒性疾病中的用途。
• US5380746A
  申请人：——

  公开号：US5380746A

  公开（公告）日：1995-01-10
• US5516915A
  申请人：——

  公开号：US5516915A

  公开（公告）日：1996-05-14
• [EN] METHODS AND COMPOSITIONS FOR IMPROVING HOMING OF CELLS INCLUDING MESENCHYMAL STEM CELLS<br/>[FR] PROCÉDÉS ET COMPOSITIONS POUR AMÉLIORER LE GUIDAGE DE CELLULES SOUCHES MÉSENCHYMATEUSES
  申请人：SANOFI SA

  公开号：WO2015112602A1

  公开（公告）日：2015-07-30

  The disclosure relates to methods and compositions for improving homing of cells including mesenchymal stem cells (MSCs). Compositions include compounds described herein as capable of inducing expression by MSCs of cell surface homing ligand molecules such as CD1 la, promoting increased firm adhesion by MSCs in an in vitro shear flow assay, increasing binding to an adhesion molecule such as E-selectin or ICAM-1, and/or demonstrating anti-inflammatory activity upon in vivo systemic administration in cell therapy using human MSCs. Also described are screening methods to identify small molecule compounds for improving a homing function of MSCs.
• Synthesis, Structure−Activity Relationship, and Biological Studies of Indolocarbazoles as Potent Cyclin D1-CDK4 Inhibitors
  作者：Guoxin Zhu、Scott E. Conner、Xun Zhou、Chuan Shih、Tiechao Li、Bryan D. Anderson、Harold B. Brooks、Robert Morris Campbell、Eileen Considine、Jack A. Dempsey、Margaret M. Faul、Cathy Ogg、Bharvin Patel、Richard M. Schultz、Charles D. Spencer、Beverly Teicher、Scott A. Watkins

  DOI：10.1021/jm0256169

  日期：2003.5.1

  Novel substituted indolocarbazoles were synthesized, and their kinase inhibitory capability was evaluated in vitro. 6-Substituted indolocarbazoles 4 were found to be potent and selective D1/CDK4 inhibitors. 4d and 4h exhibited potent and ATP-competitive D1/CDK4 activities with IC50 values of 76 and 42 nM, respectively. Both compounds had high selectivity against the other kinases. These D1/CDK4 inhibitors inhibited tumor cell growth, arrested tumor cells at the G1 phase, and inhibited pRb phosphorylation.