12,13-Dihydro-2,10-dimethoxy-5H-Indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione | 118458-57-4

• 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: 12,13-Dihydro-2,10-dimethoxy-5H-Indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione
• 英文别名: 6,20-dimethoxy-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione
• CAS: 118458-57-4
• 化学式: C₂₂H₁₅N₃O₄
• 分子量: 385.379
• InChiKey: PHOPMJNJEYAORG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12,13-Dihydro-2,10-dimethoxy-5H-Indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione 在 吡啶盐酸盐 作用下， 反应 1.0h， 以31%的产率得到arcyriaflavin C
  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：

  5,6-Bis-[(3-methoxy-phenyl)-hydrazono]-hexahydro-isoindole-1,3-dione 在 polyphosphoric acid trimethyl silyl ether 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 12,13-Dihydro-2,10-dimethoxy-5H-Indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione
  参考文献：
  名称：

  Synthesis of indolo[2,3-a]pyrrolo[3,4-c]carbazoles by double Fischer indolizations

  摘要：

  DOI：

  10.1021/jo00265a020

文献信息

• BERGMAN, JAN;PELCMAN, BENJAMIN, J. ORG. CHEM., 54,(1989) N, C. 824-828
  作者：BERGMAN, JAN、PELCMAN, BENJAMIN

  DOI：——

  日期：——
• 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.
• Synthesis of indolo[2,3-a]pyrrolo[3,4-c]carbazoles by double Fischer indolizations
  作者：Jan Bergman、Benjamin Pelcman

  DOI：10.1021/jo00265a020

  日期：1989.2