2,5-bis(pyridin-4-ylethynyl)furan | 277306-59-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2,5-bis(pyridin-4-ylethynyl)furan
• 英文别名: 2,5-bis(4-ethynylpyridyl)furan；2,5-bis(4'-pyridylethynyl)furan；BPEB；4-[2-[5-(2-Pyridin-4-ylethynyl)furan-2-yl]ethynyl]pyridine
• CAS: 277306-59-9
• 化学式: C₁₈H₁₀N₂O
• 分子量: 270.29
• InChiKey: FASWKGOEFGHELG-UHFFFAOYSA-N

物化性质

• 沸点：
  492.2±40.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-diaquobis(1,1,1,5,5,5-hexafluoroacetylacetonato)zinc(II) 、 2,5-bis(pyridin-4-ylethynyl)furan 以 丙酮 为溶剂， 以70%的产率得到[(1,1,1,5,5,5-hexafluoroacetylacetonate)2Zn(2,5-bis(4-ethynylpyridyl)furan)](n)
  参考文献：
  名称：

  螺旋和间规锌基配位聚合物的制备，表征和X射线晶体结构。

  摘要：

  （facac）2Zn.2H2O（facac = 1,1,1,5,5,5-六氟乙酰丙酮）与2,5-双（4-乙炔基吡啶基）呋喃（1）和1,2-双（4-乙炔基吡啶基）苯（2）结晶后生成配位聚合物。前一种聚合物（（facac）2Zn.1）n在固态下具有等规螺旋结构[单斜空间群P2（1）/ n; a = 11.0374（3）A，b = 24.2179（10）A，c = 14.3970（4）A，β= 92.880（2）度；Z = 4]。后者的聚合物（（facac）2Zn.2）n在固态时为间同结构[单斜空间群P2（1）/ n; a = 9.1344（1）A，b = 21.7985（5）A，c = 16.0322（4）A，beta = 99.6680（11）度; Z = 4]。相应的低聚物的溶液结构已通过低温1H和19F NMR光谱进行了研究。使用片段[（+）-tfc] 2 Zn（（+）-tfc = 3-

  DOI：

  10.1021/ic991315m

文献信息

• Self-Assembly with Postmodification:  Kinetically Stabilized Metalla-Supramolecular Rectangles
  作者：Christopher J. Kuehl、Songping D. Huang、Peter J. Stang

  DOI：10.1021/ja0114355

  日期：2001.10.1

  Interaction of a predesigned molecular "clip" (4) with rigid dipyridyl bridging ligands, in acetone/ water mixtures, leads to the formation of molecular rectangles (5-8) in 92-97% isolated yields via spontaneous self-assembly. Characterization was accomplished with multinuclear NMR and UV-vis spectroscopy, FAB mass spectrometry, and X-ray crystallography. The length of these metallamacrocycles ranges from 2 to 3 nm. Postmodification via non-nucleophilic counterion exchange results in enhanced structural integrity for the assemblies.
• Anticancer Activity and Autophagy Involvement of Self-Assembled Arene–Ruthenium Metallacycles
  作者：Abhishek Dubey、Yong Joon Jeong、Jae Ho Jo、Sangkook Woo、Dong Hwan Kim、Hyunuk Kim、Se Chan Kang、Peter J. Stang、Ki-Whan Chi

  DOI：10.1021/acs.organomet.5b00512

  日期：2015.9.28

  A suite of six metallacycles (16) was generated via coordination-driven self-assembly using the three dicarboxylate-bridged areneRu precursors [Ru-2(mu-eta(4)-OO boolean AND OO)(eta(6)-p-iPrC(6)H4Me)(2)][CF3SO3](2); (OO boolean AND OO = oxalate (A1), 2,5-dihydroxy-1,4-benzoquinonato (dobq) (A2), 5,8-dihydroxy-1,4-naphthoquinonato (donq) (A3); CF3SO3 = triflate) with one of two dipyridyl ligands (L1 and L2). The metallacycles were isolated in excellent yield (8692%) as triflate salts and characterized by proton (H-1) and carbon-13 (C-13) nuclear magnetic resonance (NMR) and electrospray ionizationmass spectrometry (ESI-MS) to confirm their structural assignments. Single-crystal X-ray crystal analysis of 1 revealed that two L1 ligands bridged two A1 acceptors to form a rectangular architecture. The 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay was conducted to evaluate the in vitro cytotoxicities relative to two chemotherapeutic agents: namely, cisplatin and doxorubicin. Metallacycles 3 and 6 potently inhibited the growth of HCT-15 human colon and AGS human gastric cancer cells. The hollow fiber (HF) assay was performed to investigate the in vivo antitumor activities of metallacycles 3 and 6. Metallacycle 6 was more effective in inhibiting HCT-15 cells than metallacycle 3 in both in vitro and in vivo studies. Moreover, 3 and 6 induced autophagic activity in HCT-15 cells. These results suggested that the autophagic response elicited by metallacycles 3 and 6 could mediate the anticancer effects observed in human colorectal cancer cells.