1-(tert-butoxycarbonyl)-2-[(4-cyano-3-fluorophenyl)ethynyl]-1H-indole-6-carbonitrile | 1214278-94-0

• 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: 1-(tert-butoxycarbonyl)-2-[(4-cyano-3-fluorophenyl)ethynyl]-1H-indole-6-carbonitrile
• CAS: 1214278-94-0
• 化学式: C₂₃H₁₆FN₃O₂
• 分子量: 385.397
• InChiKey: LFTMQKDWKBWPBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  29.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  78.81
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(tert-butoxycarbonyl)-2-[(4-cyano-3-fluorophenyl)ethynyl]-1H-indole-6-carbonitrile 在 lithium hexamethyldisilazane 、 盐酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 72.0h， 以51%的产率得到2-[(4-amidino-3-fluorophenyl)ethynyl]-6-amidino-1H-indole dihydrochloride
  参考文献：
  名称：

  Synthesis, DNA binding, fluorescence measurements and antiparasitic activity of DAPI related diamidines

  摘要：

  A novel series of extended DAPI analogues were prepared by insertion of either a carbon-carbon triple bond (16a-d) or a phenyl group (21a, b and 24) at position-2. The new amidines were evaluated in vitro against both Trypanosoma brucei rhodesiense (T. b. r.) and Plasmodium falciparum (P. f.). Five compounds (16a, 16b, 16d, 21a, 21b) exhibited IC50 values against T. b. r. of 9 nM or less which is two to nine folds more effective than DAPI. The same five compounds exhibited IC50 values against P. f. of 5.9 nM or less which is comparable to that of DAPI. The fluorescence properties of these new molecules were recorded, however; they do not offer any advantage over those of DAPI. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.011
• 作为产物：
  描述：

  4-乙炔基-2-氟苯甲腈 、 1-(tert-butoxycarbonyl)-2-iodo-1H-indole-6-carbonitrile 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以80%的产率得到1-(tert-butoxycarbonyl)-2-[(4-cyano-3-fluorophenyl)ethynyl]-1H-indole-6-carbonitrile
  参考文献：
  名称：

  Synthesis, DNA binding, fluorescence measurements and antiparasitic activity of DAPI related diamidines

  摘要：

  A novel series of extended DAPI analogues were prepared by insertion of either a carbon-carbon triple bond (16a-d) or a phenyl group (21a, b and 24) at position-2. The new amidines were evaluated in vitro against both Trypanosoma brucei rhodesiense (T. b. r.) and Plasmodium falciparum (P. f.). Five compounds (16a, 16b, 16d, 21a, 21b) exhibited IC50 values against T. b. r. of 9 nM or less which is two to nine folds more effective than DAPI. The same five compounds exhibited IC50 values against P. f. of 5.9 nM or less which is comparable to that of DAPI. The fluorescence properties of these new molecules were recorded, however; they do not offer any advantage over those of DAPI. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.011