2-[(E)-1-ethyl-1-pentyl]-indole | 606138-16-3

• 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: 2-[(E)-1-ethyl-1-pentyl]-indole
• 英文别名: 2-[(E)-hept-3-en-3-yl]-1H-indole
• CAS: 606138-16-3
• 化学式: C₁₅H₁₉N
• 分子量: 213.323
• InChiKey: GJTFYLXUKPLSNX-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  马来酰亚胺 、 2-[(E)-1-ethyl-1-pentyl]-indole 以61%的产率得到5-Ethyl-4-propyl-5,6-dihydro-4H-pyrrolo[3,4-c]carbazole-1,3-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：

  (2-氨基苯甲基)三苯基溴化膦 在 吡啶 、 potassium tert-butylate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 2-[(E)-1-ethyl-1-pentyl]-indole
  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

• Synthesis and biological evaluation of structural variants of carbazoquinocin C
  作者：Alparslan Aygün、Ulf Pindur

  DOI：10.1002/jhet.5570400303

  日期：2003.5

  Some new structural variants of the alkaloid carbazoquinocin C were synthesized in a few steps with good to excellent yields. The key step comprises a cyclisation reaction of appropriate 2-vinylindoles with oxalyl chloride. The carbazole-3,4-quinones are able to trap oxygen-centred radicals. In some biological/biochemical assays some of these compounds exhibit extraordinary results including inhibition

  生物碱咔唑喹啉C的一些新的结构变体是通过几步合成的，合成的产率高到极好。关键步骤包括适当的2-乙烯基吲哚与草酰氯的环化反应。咔唑-3,4-醌能够捕获以氧为中心的自由基。在某些生物/生化测定中，这些化合物中的某些表现出非凡的结果，包括在μM范围内抑制环氧合酶-1和5-脂氧合酶。而且，一些咔唑喹啉C变体在nM范围内抑制细胞DNA的显着氧化损伤。
• 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.