N-(4-(pyridinyl-4-ethynyl)phenyl)-isonicotinamide | 1372619-76-5

• 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: N-(4-(pyridinyl-4-ethynyl)phenyl)-isonicotinamide
• 英文别名: N-[4-(pyridin-4-ylethynyl)phenyl]isonicotinamide；N-[4-(2-pyridin-4-ylethynyl)phenyl]pyridine-4-carboxamide
• CAS: 1372619-76-5
• 化学式: C₁₉H₁₃N₃O
• 分子量: 299.332
• InChiKey: RPLHHJVMBVGTCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 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：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [Ru₂(μ-η⁴-C₂O₄)(MeOH)₂(η⁶-p-iPrC₆H₄Me)₂][O₃SCF₃]₂ 、 N-(4-(pyridinyl-4-ethynyl)phenyl)-isonicotinamide 以 甲醇 、 二氯甲烷 为溶剂， 以92%的产率得到
  参考文献：
  名称：

  Anticancer Activity of Self-Assembled Molecular Rectangles via Arene–Ruthenium Acceptors and a New Unsymmetrical Amide Ligand

  摘要：

  Two new and large molecular rectangles 4 and 5 were synthesized from two different arene-ruthenium [Ru-2(mu-eta(4)-C2O4)(MeOH)(2)(eta(6)-p-(PrC6H4Me)-C-i)(2)][O3SCF3](2) (2) and [Ru-2(p-cymene)(2)(donq)(OH2)(2)][O3SCF3](2) (donq = 5,8-dioxydo-1,4-naphthaquinonato) (3) acceptors and a new unsymmetrical N-(4-(pyridin-4-ylethynyl)phenyl) isonicotinamide (1) donor ligand. Xray crystallography of 4 confirmed a molecular rectangle. The H-1 NMR spectra of both rectangles 4 and 5 showed a mixture of two structural, head-to-tail (HTT) and head-to-head (HTH), type isomers in a 1:1 ratio. The cytotoxicities, of both rectangles have been established against Colo320 (colorectal cancer), A549 (lung cancer), MCF-7 (breast cancer), and H1299 (lung cancer) human cancer,cell lines. The cytotoxicity of rectangle 5 was found to be considerably stronger against all cancer cell lines than that of the reference drug cisplatin.

  DOI：

  10.1021/om2012826
• 作为产物：
  描述：

  N-(4-iodophenyl)-4-pyridinecarboxamide 、 4-ethynylpyridine hydrochloride 在 三乙胺 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.33h， 以72%的产率得到N-(4-(pyridinyl-4-ethynyl)phenyl)-isonicotinamide
  参考文献：
  名称：

  Anticancer Activity of Self-Assembled Molecular Rectangles via Arene–Ruthenium Acceptors and a New Unsymmetrical Amide Ligand

  摘要：

  Two new and large molecular rectangles 4 and 5 were synthesized from two different arene-ruthenium [Ru-2(mu-eta(4)-C2O4)(MeOH)(2)(eta(6)-p-(PrC6H4Me)-C-i)(2)][O3SCF3](2) (2) and [Ru-2(p-cymene)(2)(donq)(OH2)(2)][O3SCF3](2) (donq = 5,8-dioxydo-1,4-naphthaquinonato) (3) acceptors and a new unsymmetrical N-(4-(pyridin-4-ylethynyl)phenyl) isonicotinamide (1) donor ligand. Xray crystallography of 4 confirmed a molecular rectangle. The H-1 NMR spectra of both rectangles 4 and 5 showed a mixture of two structural, head-to-tail (HTT) and head-to-head (HTH), type isomers in a 1:1 ratio. The cytotoxicities, of both rectangles have been established against Colo320 (colorectal cancer), A549 (lung cancer), MCF-7 (breast cancer), and H1299 (lung cancer) human cancer,cell lines. The cytotoxicity of rectangle 5 was found to be considerably stronger against all cancer cell lines than that of the reference drug cisplatin.

  DOI：

  10.1021/om2012826

文献信息

• Selective Detection of Multicarboxylate Anions based on “Turn on” Electron Transfer by Self‐Assembled Molecular Rectangles
  作者：Anurag Mishra、Sunmi Lee、Hyunuk Kim、Timothy R. Cook、Peter J. Stang、Ki‐Whan Chi

  DOI：10.1002/asia.201200488

  日期：2012.11

  tetranuclear cations of the general formula [Ru4(arene)4()2(O O)2]4+. Both rectangles were isolated in good yields as triflate salts and were characterized by multinuclear NMR, ESI‐MS, UV/Vis, and photoluminescence spectroscopy. The crystal structure of 5 was determined by X‐ray diffraction. Luminescent rectangle 5 was used for anion sensing with an amide ligand as a hydrogen‐bond donor and an arene–ruthenium

  通过两种不同的双核芳烃钌配合物[Ru 2 ( arene ) 2 (O O) 2 Cl 2 ] (arene= p ‐伞花烃; O O = 2,5 -二羟基-1,4-苯醌 ( 2 )、6,11-二羟基-5,12-并四苯二酸 ( 3 )) 与不对称酰胺( N- [4-(吡啶-4-基乙炔基)苯基]异烟酰胺) 供体配体1在甲醇中在AgO 3 SCF 3存在下，形成通式[Ru 4 (芳烃) 4 ( ) 2 (O O) 2 ] 4+的四核阳离子。这两个矩形均以三氟甲磺酸盐的形式以良好的产率分离出来，并通过多核 NMR、ESI-MS、UV/Vis 和光致发光光谱进行了表征。通过X射线衍射测定了5的晶体结构。发光矩形5用于阴离子传感，其中酰胺配体作为氢键供体，芳烃-钌受体作为信号单元。矩形5在 UV/Vis 滴定实验中以 1:1 的比例强烈结合多羧酸根阴离子，例如草酸根、酒石酸根和柠檬酸根，与单阴离子（例如
• Cadmium(II) and zinc(II) coordination polymers built with an ethynyl backbone containing an unsymmterical amide ligand: Syntheses, crystal structures, and photoluminescent properties
  作者：Anurag Mishra、Hyunuk Kim、Seung Chang Lee、JinWook Min、Min Hyung Lee、Ki-Whan Chi

  DOI：10.1016/j.ica.2013.05.004

  日期：2013.8

  Two new crystalline coordination polymers have been synthesized with Zn2+ and Cd2+ ions using an N-(4-(pyridinyl-4-ethynyl)phenyl)-isonicotinamide (HL) donor ligand. The ligand readily reacts with metal nitrate in DMF to afford 1-dimensional (1D) coordination polymers 1 and 2 comprising a repeating unit of [Zn(HL)(NO3)(2)(DMF)]center dot DMF and [Cd(HL)(NO3)(2)(DMF)]center dot DMF, respectively. Both complexes 1 and 2 were characterized by IR spectroscopy, elemental analysis, thermogravimetric analysis (TGA), and X-ray diffraction. Both complexes contained a 1D chain in which crystallography revealed two metal ions were connected by each ligand. The weak pi-pi stacking interactions and intermolecular hydrogen bonds resulted in the one-dimensional network structures. The photoluminescent properties for both complexes were also investigated. (C) 2013 Elsevier B.V. All rights reserved.
• Anticancer Activity of Self-Assembled Molecular Rectangles via Arene–Ruthenium Acceptors and a New Unsymmetrical Amide Ligand
  作者：Anurag Mishra、Hyunji Jung、Jeong Woo Park、Hong Kyeung Kim、Hyunuk Kim、Peter J. Stang、Ki-Whan Chi

  DOI：10.1021/om2012826

  日期：2012.5.14

  Two new and large molecular rectangles 4 and 5 were synthesized from two different arene-ruthenium [Ru-2(mu-eta(4)-C2O4)(MeOH)(2)(eta(6)-p-(PrC6H4Me)-C-i)(2)][O3SCF3](2) (2) and [Ru-2(p-cymene)(2)(donq)(OH2)(2)][O3SCF3](2) (donq = 5,8-dioxydo-1,4-naphthaquinonato) (3) acceptors and a new unsymmetrical N-(4-(pyridin-4-ylethynyl)phenyl) isonicotinamide (1) donor ligand. Xray crystallography of 4 confirmed a molecular rectangle. The H-1 NMR spectra of both rectangles 4 and 5 showed a mixture of two structural, head-to-tail (HTT) and head-to-head (HTH), type isomers in a 1:1 ratio. The cytotoxicities, of both rectangles have been established against Colo320 (colorectal cancer), A549 (lung cancer), MCF-7 (breast cancer), and H1299 (lung cancer) human cancer,cell lines. The cytotoxicity of rectangle 5 was found to be considerably stronger against all cancer cell lines than that of the reference drug cisplatin.