4,5,6,7-tetrahydrobenzo[a]pyrrolo[3,4-c]carbazole-1,3(2H,8H)-dione | 374071-06-4

• 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: 4,5,6,7-tetrahydrobenzo[a]pyrrolo[3,4-c]carbazole-1,3(2H,8H)-dione
• 英文别名: 4,14-Diazapentacyclo[11.7.0.0^{2,6}.0^{7,12}.0^{15,20}]icosa-1(13),2(6),7(12),15,17,19-hexaene-3,5-dione；4,14-diazapentacyclo[11.7.0.02,6.07,12.015,20]icosa-1(13),2(6),7(12),15,17,19-hexaene-3,5-dione
• CAS: 374071-06-4
• 化学式: C₁₈H₁₄N₂O₂
• 分子量: 290.321
• InChiKey: XCUWUKJYHFLWPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5,6,7-tetrahydrobenzo[a]pyrrolo[3,4-c]carbazole-1,3(2H,8H)-dione 在 palladium on activated charcoal 1-己烯 作用下， 生成 benzo[a]pyrrolo[3,4-c]carbazole-1,3(2H,8H)-dione
  参考文献：
  名称：

  Synthesis and structure–activity relationships of novel poly(ADP-ribose) polymerase-1 inhibitors

  摘要：

  A series of novel pyrrolocarbazoles was synthesized as potential PARP-1 inhibitors. Pyrrolocarbazole 1 was identified as a potent PARP-I inhibitor (IC50 = 36 nM) from our internal database. Synthesis of analogs around this template with the aid of modeling studies led to the identification of the truncated imide 14. Compound 14 (IC50 = 40 nM), with deleted B-ring, was found to be an equipotent PARP-1 inhibitor. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.099
• 作为产物：
  描述：

  1-(1H-吲哚-2-基)环己烷-1-醇 在 盐酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 4,5,6,7-tetrahydrobenzo[a]pyrrolo[3,4-c]carbazole-1,3(2H,8H)-dione
  参考文献：
  名称：

  Synthesis and structure–activity relationships of novel poly(ADP-ribose) polymerase-1 inhibitors

  摘要：

  A series of novel pyrrolocarbazoles was synthesized as potential PARP-1 inhibitors. Pyrrolocarbazole 1 was identified as a potent PARP-I inhibitor (IC50 = 36 nM) from our internal database. Synthesis of analogs around this template with the aid of modeling studies led to the identification of the truncated imide 14. Compound 14 (IC50 = 40 nM), with deleted B-ring, was found to be an equipotent PARP-1 inhibitor. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.099

文献信息

• Efficient Synthesis of Maleimides and Carbazoles via Zn(OTf)₂-Catalyzed Tandem Annulations of Isonitriles and Allenic Esters
  作者：Yuanzhen Li、Haixia Zou、Jianxian Gong、Jing Xiang、Tuoping Luo、Junmin Quan、Guoxin Wang、Zhen Yang

  DOI：10.1021/ol7018086

  日期：2007.9.1

  Lewis acid Zn(OTf)(2)-catalyzed tandem annulations of isonitriles and allenic esters which lead to efficient and flexible syntheses of a range of biologically significant maleimides and carbazoles and related compounds are reported. A mechanistic rationale is proposed to account for the observed reactivity.
• Synthesis and structure–activity relationships of novel poly(ADP-ribose) polymerase-1 inhibitors
  作者：Ming Tao、Chung Ho Park、Ron Bihovsky、Gregory J. Wells、Jean Husten、Mark A. Ator、Robert L. Hudkins

  DOI：10.1016/j.bmcl.2005.10.099

  日期：2006.2

  A series of novel pyrrolocarbazoles was synthesized as potential PARP-1 inhibitors. Pyrrolocarbazole 1 was identified as a potent PARP-I inhibitor (IC50 = 36 nM) from our internal database. Synthesis of analogs around this template with the aid of modeling studies led to the identification of the truncated imide 14. Compound 14 (IC50 = 40 nM), with deleted B-ring, was found to be an equipotent PARP-1 inhibitor. (c) 2005 Elsevier Ltd. All rights reserved.