2,3-bis-(4-fluoro-1H-indol-3-yl)-N-methylmaleimide | 152537-98-9

• 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: 2,3-bis-(4-fluoro-1H-indol-3-yl)-N-methylmaleimide
• 英文别名: 3,4-bis(4-fluoro-1H-indol-3-yl)-1-methylpyrrole-2,5-dione
• CAS: 152537-98-9
• 化学式: C₂₁H₁₃F₂N₃O₂
• 分子量: 377.35
• InChiKey: FFPZJAYNDSLJFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  69
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-bis-(4-fluoro-1H-indol-3-yl)-N-methylmaleimide 在 氢氧化钾 作用下， 以 1,4-二氧六环 为溶剂， 以100%的产率得到2,3-bis-(4-fluoro-1H-indol-3-yl)-maleic anhydride
  参考文献：
  名称：

  Indolocarbazoles: potent, selective inhibitors of human cytomegalovirus replication

  摘要：

  In our search for new, safer anti-HCMV agents, we discovered that the natural product Arcyriaflavin A (la) was a potent inhibitor of HCMV replication in cell culture. A series of analogues (symmetrical indolocarbazoles) was synthesised to investigate structure-activity relationships in this series against a range of herpes viruses (HCMV, VZV, HSV1, and 2). This identified a number of novel, selective and potent inhibitors of HCMV, 12,13-dihydro-2,10-difluoro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-(6H)-dione (Id) being the best example (IC50 = 40 nM, therapeutic index > 1450). Compounds described in this series were generally poor inhibitors of protein kinase C beta II, and no correlation was found between the ability to inhibit HCMV and the enzyme PKC. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00032-2
• 作为产物：
  描述：

  4-氟吲哚 、 2,3-二氯-N-甲基马来酰亚胺顺丁烯二酰亚胺 在 乙基溴化镁 作用下， 以 四氢呋喃 、 苯 为溶剂， 以26%的产率得到2,3-bis-(4-fluoro-1H-indol-3-yl)-N-methylmaleimide
  参考文献：
  名称：

  Indolocarbazoles: potent, selective inhibitors of human cytomegalovirus replication

  摘要：

  In our search for new, safer anti-HCMV agents, we discovered that the natural product Arcyriaflavin A (la) was a potent inhibitor of HCMV replication in cell culture. A series of analogues (symmetrical indolocarbazoles) was synthesised to investigate structure-activity relationships in this series against a range of herpes viruses (HCMV, VZV, HSV1, and 2). This identified a number of novel, selective and potent inhibitors of HCMV, 12,13-dihydro-2,10-difluoro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-(6H)-dione (Id) being the best example (IC50 = 40 nM, therapeutic index > 1450). Compounds described in this series were generally poor inhibitors of protein kinase C beta II, and no correlation was found between the ability to inhibit HCMV and the enzyme PKC. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00032-2

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.
• Indolocarbazoles: potent, selective inhibitors of human cytomegalovirus replication
  作者：Martin J. Slater、Stuart Cockerill、Robert Baxter、Robert W. Bonser、Kam Gohil、Clare Gowrie、J.Edward Robinson、Edward Littler、Nigel Parry、Roger Randall、Wendy Snowden

  DOI：10.1016/s0968-0896(99)00032-2

  日期：1999.6

  In our search for new, safer anti-HCMV agents, we discovered that the natural product Arcyriaflavin A (la) was a potent inhibitor of HCMV replication in cell culture. A series of analogues (symmetrical indolocarbazoles) was synthesised to investigate structure-activity relationships in this series against a range of herpes viruses (HCMV, VZV, HSV1, and 2). This identified a number of novel, selective and potent inhibitors of HCMV, 12,13-dihydro-2,10-difluoro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-(6H)-dione (Id) being the best example (IC50 = 40 nM, therapeutic index > 1450). Compounds described in this series were generally poor inhibitors of protein kinase C beta II, and no correlation was found between the ability to inhibit HCMV and the enzyme PKC. (C) 1999 Elsevier Science Ltd. All rights reserved.