3-((4-fluorophenyl)ethynyl)aniline | 138781-97-2

• 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: 3-((4-fluorophenyl)ethynyl)aniline
• 英文别名: 3-[(4-Fluorophenyl)ethynyl]aniline；3-[2-(4-fluorophenyl)ethynyl]aniline
• CAS: 138781-97-2
• 化学式: C₁₄H₁₀FN
• mdl: MFCD12156106
• 分子量: 211.239
• InChiKey: XBKVTMPLFNPJLY-UHFFFAOYSA-N

物化性质

• 沸点：
  372.7±27.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-((4-fluorophenyl)ethynyl)aniline 、 4-aminobenzamidine dihydrochloride 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.5h， 以58%的产率得到(E)-4-(3-(3-((4-fluorophenyl)ethynyl)phenyl)triaz-1-enyl)benzimidamide
  参考文献：
  名称：

  Alkyne-substituted diminazene as G-quadruplex binders with anticancer activities

  摘要：

  G-quadruplex ligands have been touted as potential anticancer agents, however, none of the reported G-quadruplex-interactive small molecules have gone past phase II clinical trials. Recently it was revealed that diminazene (berenil, DMZ) actually binds to G-quadruplexes 1000 times better than DNA duplexes, with dissociation constants approaching 1 nM. DMZ however does not have strong anticancer activities. In this paper, using a panel of biophysical tools, including NMR, FRET melting assay and FRET competition assay, we discovered that monoamidine analogues of DMZ bearing alkyne substitutes selectively bind to G-quadruplexes. The lead DMZ analogues were shown to be able to target c-MYC G-quadruplex both in vitro and in vivo. Alkyne DMZ analogues display respectable anticancer activities (single digit micromolar GI(50)) against ovarian (OVCAR-3), prostate (PC-3) and triple negative breast (MDA-MB-231) cancer cell lines and represent interesting new leads to develop anticancer agents. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.04.030
• 作为产物：
  描述：

  对氟碘苯 、 3-氨基苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 、 三苯基膦 作用下， 反应 16.0h， 以83%的产率得到3-((4-fluorophenyl)ethynyl)aniline
  参考文献：
  名称：

  Alkyne-substituted diminazene as G-quadruplex binders with anticancer activities

  摘要：

  G-quadruplex ligands have been touted as potential anticancer agents, however, none of the reported G-quadruplex-interactive small molecules have gone past phase II clinical trials. Recently it was revealed that diminazene (berenil, DMZ) actually binds to G-quadruplexes 1000 times better than DNA duplexes, with dissociation constants approaching 1 nM. DMZ however does not have strong anticancer activities. In this paper, using a panel of biophysical tools, including NMR, FRET melting assay and FRET competition assay, we discovered that monoamidine analogues of DMZ bearing alkyne substitutes selectively bind to G-quadruplexes. The lead DMZ analogues were shown to be able to target c-MYC G-quadruplex both in vitro and in vivo. Alkyne DMZ analogues display respectable anticancer activities (single digit micromolar GI(50)) against ovarian (OVCAR-3), prostate (PC-3) and triple negative breast (MDA-MB-231) cancer cell lines and represent interesting new leads to develop anticancer agents. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.04.030

文献信息

• Fluorinated acetylene-containing aromatic amines and diamines
  申请人：National Starch and Chemical Investment Holding Corporation

  公开号：US05107026A1

  公开（公告）日：1992-04-21

  A class of fluorinated phenylethynylaniline compounds is disclosed, said compounds having a use as capping reagents in high temperature stable polyimides or other polymers having a functionality which can undergo reaction with the amine to form a stable adduct. The diamine compounds of the invention are useful as step-growth monomers in the preparation of polymers containing reactive acetylene groups in the polymer backbone.

  本发明揭示了一类氟化苯乙炔基苯胺化合物，这些化合物具有作为封端试剂在高温稳定聚酰亚胺或其他具有可以与胺发生反应形成稳定加合物的官能团的聚合物中的用途。本发明的二胺化合物在含有聚合物主链中具有反应性乙炔基团的聚合物的制备中作为步骤增长单体是有用的。
• Polyimides end-capped with diaryl substituted acetylene
  申请人：National Starch and Chemical Investment Holding Corporation

  公开号：EP0443352A2

  公开（公告）日：1991-08-28

  Polyimide and polyisoimide oligomers and precursors thereof, wherein said polymerizable oligomer is end-capped with a diaryl substituted acetylen (DASA) having the general formula: wherein m = 0 to 5, L=O to 4, R and R¹ are independently selected from the group consisting of halogen (such as fluorine), C₁-C₄ alkyl, alkoxy, aryloxy, haloaryl, haloalkyl, haloacyl, and aryl, acyl, and X is a linking group to the oligomer backbone selected from the group consisting of NH₂, CHO, isocyanate, anhydride, carboxylic acid, ester, acyl halides; The polyimide or polyisoimide oligomers are useful for composites, molding compounds, adhesives, and electronic applications.

  聚酰亚胺和聚异丁烯亚胺低聚物及其前体，其中所述可聚合低聚物以具有通式的二芳基取代乙炔（DASA）为端盖： 其中 m=0 至 5，L=O 至 4，R 和 R¹ 独立选自由卤素（如氟）、C₁-C₄ 烷基、烷氧基、芳氧基、卤代芳基、卤代烷基、卤代酰基和芳基组成的组、X 是与低聚物骨架的连接基团，选自 NH₂、CHO、异氰酸酯、酸酐、羧酸、酯、酰卤组成的组； 聚酰亚胺或聚异亚胺低聚物可用于复合材料、模塑化合物、粘合剂和电子应用。
• LINKED DIARYL COMPOUNDS WITH ANTICANCER PROPERTIES AND METHODS OF USING THE SAME
  申请人：University of Maryland, College Park

  公开号：US20170174620A1

  公开（公告）日：2017-06-22

  Provided are compositions comprising linked diaryl compounds that possess anticancer properties. Methods of use are also disclosed herein. The method comprises administering an effective amount of a compound described herein to an individual in need thereof.
• US5107026A
  申请人：——

  公开号：US5107026A

  公开（公告）日：1992-04-21
• US5138028A
  申请人：——

  公开号：US5138028A

  公开（公告）日：1992-08-11