4-(1H-indol-6-yl)benzonitrile | 215237-43-7

• 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-(1H-indol-6-yl)benzonitrile
• CAS: 215237-43-7
• 化学式: C₁₅H₁₀N₂
• 分子量: 218.258
• InChiKey: XIGGKXHJIDYKMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 4-(1H-indol-6-yl)benzonitrile 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到1-(tert-butoxycarbonyl)-6-(4-cyanophenyl)-1H-indole
  参考文献：
  名称：

  Exploration of larger central ring linkers in furamidine analogues: Synthesis and evaluation of their DNA binding, antiparasitic and fluorescence properties

  摘要：

  The effects of replacing the central furan ring of furamidine with indole and benzimidazole on their DNA binding affinity, antiparasitic activity and fluorescence are reported. The bis-cyanophenylindoles required to make the corresponding amidines were prepared by sequential Stille and/or Suzuki coupling reactions. The bis-cyanophenylbenzimidazoles were obtained by coupling 4-cyanobenzaldehydes with the appropriate cyano substituted phenylenediamine. The bis-nitriles were converted to the diamidines by reaction with LiN[Si(CH3)(3)](2) or by Pinner methodology. Specifically, we have prepared new series of 2,6- and 2,5-diaryl indoles (6a, b, 12 and 17a-d) and the related benzimidazoles (24, 30 and 35). The new compounds bind in the DNA minor groove in DNA AT base pair sequences and eight of the ten new analogues exhibit Delta T-m values comparable to or higher than that of furamidine. Six of ten of the new compounds exhibit lower IC50 values against Trypanosoma brucei rhodesiense (T. b. r.) and eight of ten exhibit lower IC50 values against Plasmodium falciparum (P. f.) than furamidine. Four of the ten show greater efficacy than furamidine in the rigorous T. b. r. STIB900 mouse model for African trypanosomiasis. Generally, the fluorescence properties of the new analogues are similar to that of DAPI. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.045
• 作为产物：
  描述：

  6-溴吲哚 、 4-氰基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲苯 为溶剂， 以30%的产率得到4-(1H-indol-6-yl)benzonitrile
  参考文献：
  名称：

  Exploration of larger central ring linkers in furamidine analogues: Synthesis and evaluation of their DNA binding, antiparasitic and fluorescence properties

  摘要：

  The effects of replacing the central furan ring of furamidine with indole and benzimidazole on their DNA binding affinity, antiparasitic activity and fluorescence are reported. The bis-cyanophenylindoles required to make the corresponding amidines were prepared by sequential Stille and/or Suzuki coupling reactions. The bis-cyanophenylbenzimidazoles were obtained by coupling 4-cyanobenzaldehydes with the appropriate cyano substituted phenylenediamine. The bis-nitriles were converted to the diamidines by reaction with LiN[Si(CH3)(3)](2) or by Pinner methodology. Specifically, we have prepared new series of 2,6- and 2,5-diaryl indoles (6a, b, 12 and 17a-d) and the related benzimidazoles (24, 30 and 35). The new compounds bind in the DNA minor groove in DNA AT base pair sequences and eight of the ten new analogues exhibit Delta T-m values comparable to or higher than that of furamidine. Six of ten of the new compounds exhibit lower IC50 values against Trypanosoma brucei rhodesiense (T. b. r.) and eight of ten exhibit lower IC50 values against Plasmodium falciparum (P. f.) than furamidine. Four of the ten show greater efficacy than furamidine in the rigorous T. b. r. STIB900 mouse model for African trypanosomiasis. Generally, the fluorescence properties of the new analogues are similar to that of DAPI. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.045

文献信息

• Scope of the Suzuki−Miyaura Cross-Coupling Reactions of Potassium Heteroaryltrifluoroborates
  作者：Gary A. Molander、Belgin Canturk、Lauren E. Kennedy

  DOI：10.1021/jo802590b

  日期：2009.2.6

  A wide variety of bench-stable potassium heteroaryltrifluoroborates were prepared, and general reaction conditions were developed for their cross-coupling to aryl and heteroaryl halides. The cross-coupled products were obtained in good to excellent yields. This method represents an efficient and facile installation of heterocyclic building blocks onto preexisting organic substructures.
• Exploration of larger central ring linkers in furamidine analogues: Synthesis and evaluation of their DNA binding, antiparasitic and fluorescence properties
  作者：Abdelbasset A. Farahat、Ekaterina Paliakov、Arvind Kumar、Alaa-Eldin M. Barghash、Fatma E. Goda、Hassan M. Eisa、Tanja Wenzler、Reto Brun、Yang Liu、W. David Wilson、David W. Boykin

  DOI：10.1016/j.bmc.2011.02.045

  日期：2011.4

  The effects of replacing the central furan ring of furamidine with indole and benzimidazole on their DNA binding affinity, antiparasitic activity and fluorescence are reported. The bis-cyanophenylindoles required to make the corresponding amidines were prepared by sequential Stille and/or Suzuki coupling reactions. The bis-cyanophenylbenzimidazoles were obtained by coupling 4-cyanobenzaldehydes with the appropriate cyano substituted phenylenediamine. The bis-nitriles were converted to the diamidines by reaction with LiN[Si(CH3)(3)](2) or by Pinner methodology. Specifically, we have prepared new series of 2,6- and 2,5-diaryl indoles (6a, b, 12 and 17a-d) and the related benzimidazoles (24, 30 and 35). The new compounds bind in the DNA minor groove in DNA AT base pair sequences and eight of the ten new analogues exhibit Delta T-m values comparable to or higher than that of furamidine. Six of ten of the new compounds exhibit lower IC50 values against Trypanosoma brucei rhodesiense (T. b. r.) and eight of ten exhibit lower IC50 values against Plasmodium falciparum (P. f.) than furamidine. Four of the ten show greater efficacy than furamidine in the rigorous T. b. r. STIB900 mouse model for African trypanosomiasis. Generally, the fluorescence properties of the new analogues are similar to that of DAPI. (C) 2011 Elsevier Ltd. All rights reserved.