2'-fluoro-[1,1';4',1'']terphenyl-4,4''-bis-carbonitrile | 910547-30-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2'-fluoro-[1,1';4',1'']terphenyl-4,4''-bis-carbonitrile
• 英文别名: 2'-fluoro-4,4''-bis-cyano[1,1';4',1'']terphenyl；2'-Fluoro[1,1':4',1''-terphenyl]-4,4''-dicarbonitrile；4-[4-(4-cyanophenyl)-3-fluorophenyl]benzonitrile
• CAS: 910547-30-7
• 化学式: C₂₀H₁₁FN₂
• 分子量: 298.319
• InChiKey: QNWMMTBAWCNVLE-UHFFFAOYSA-N

物化性质

• 熔点：
  289-291 °C
• 沸点：
  512.4±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2'-fluoro-[1,1';4',1'']terphenyl-4,4''-bis-carbonitrile 在 盐酸羟胺 、 potassium tert-butylate 、 (trimethylsilyl)aminolithium 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 2'-fluoro-[1,1';4',1'']terphenyl-4,4''-bis-N-hydroxyamidine
  参考文献：
  名称：

  Synthesis, DNA Affinity, and Antiprotozoal Activity of Linear Dications:  Terphenyl Diamidines and Analogues

  摘要：

  Diamidines 10a-g and 18a, b were obtained from dinitriles 9a-g and 15a, b by treatment with lithium trimethylsilylamide or upon hydrogenation of bis-O-acetoxyamidoximes. Dinitriles 9a-g were prepared via Suzuki reactions between arylboronic acids and arylnitriles. Potential prodrugs 12a-f and 17 were prepared via methylation of the diamidoximes 11a-f and 16a. Significant DNA affinities for rigid-rod molecules were observed. Compounds 10a, 10b, 10d, 18a, and 18b show IC50 values of 5 nM or less against Trypanosoma brucei rhodesiense ( T. b. r.) and 10a, 10b, 10e, 18a, and 18b gave similar ones against Plasmodium falciparum ( P. f.). The dications, 10a, 10d, 10f, and 10g are more active than furamidine in vivo. The prodrugs are only moderately effective on oral administration. Mouse liver microsome bioconversion of the methamidoxime prodrugs is significantly reduced from that of pafuramidine and suggests that the in vivo efficacy of these prodrugs is, in part, due to poor bioconversion.

  DOI：

  10.1021/jm060470p
• 作为产物：
  描述：

  4-溴苯腈 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 25.5h， 生成 2'-fluoro-[1,1';4',1'']terphenyl-4,4''-bis-carbonitrile
  参考文献：
  名称：

  Synthesis and photophysical properties of a series of thermally stable terphenyl-bridged bisbenzimidazoles

  摘要：

  Nine novel terphenyl-bridged bisbenzimidazoles were synthesized in high yield by the condensation of o-phenylenediamines and teiphenyl dinitriles in the presence of polyphosphoric acid The bisbenzimidazoles are thermally robust with high decomposition temperatures (>346 C) and high melting transitions and emit blue light at 410 nm with fluorescence quantum yield >0 4 in solution Electrochemical studies indicate that the novel bisbenzimidazoles have a formal reduction potential in the range of -144 to -155 V and estimated electron affinities (lowest unoccupied molecular orbital levels) of 3 09-3 24 eV The results indicate their potential use as blue emitting materials in organic light-emitting diodes (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.dyepig.2010.07.006

文献信息

• Linear dicationic terphenyls and their aza analogues as antiparasitic agents
  申请人：THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：EP1736466A1

  公开（公告）日：2006-12-27

  Novel dicationic terphenyl compounds and their aza analogues. Methods for combating microbial infections with novel dicationic terphenyl compounds and their aza analogues. Processes for synthesizing novel dicationic terphenyl compounds and their aza analogues.

  小说二阳离子三苯基化合物及其氮杂环衍生物。使用小说二阳离子三苯基化合物及其氮杂环衍生物对抗微生物感染的方法。合成小说二阳离子三苯基化合物及其氮杂环衍生物的过程。
• NOVEL TERARYL COMPOUNDS AS ANTIPARASITIC AGENTS
  申请人：Tidwell Richard R.

  公开号：US20110257199A1

  公开（公告）日：2011-10-20

  Novel dicationic terphenyl compounds and their aza analogues. Methods for combating microbial infections with novel dicationic terphenyl compounds and their aza analogues. Processes for synthesizing novel dicationic terphenyl compounds and their aza analogues.

  小说二元离子三苯基化合物及其氮杂环类似物。使用小说二元离子三苯基化合物及其氮杂环类似物对抗微生物感染的方法。合成小说二元离子三苯基化合物及其氮杂环类似物的过程。
• Azaterphenyl diamidines as antileishmanial agents
  作者：Laixing Hu、Reem K. Arafa、Mohamed A. Ismail、Tanja Wenzler、Reto Brun、Manoj Munde、W. David Wilson、Sandra Nzimiro、Serene Samyesudhas、Karl A. Werbovetz、David W. Boykin

  DOI：10.1016/j.bmcl.2007.10.091

  日期：2008.1

  Eighteen diamidino azaterphenyls and analogues were evaluated as anti-leishmanials; nine of the compounds gave IC50 values less than 1 mu M, five exhibited values less than 0.40 mu M, and two gave values less than 0.10 mu M in a Leishmania donovani axenic amastigote assay. The activity of the diamidines strongly depends on the ring N-atom location relative to the amidine groups and correlates with DNA affinity. Transmission electron microscopy studies showed a dramatic dilation of the mitochondrion and evidence of disintegration of the kinetoplast of the amastigotes. (C) 2007 Elsevier Ltd. All rights reserved.
• US7964619B2
  申请人：——

  公开号：US7964619B2

  公开（公告）日：2011-06-21
• US8101636B2
  申请人：——

  公开号：US8101636B2

  公开（公告）日：2012-01-24