(N1E,N2E)-N1,N2-bis(1-(pyrazin-2-yl)ethylidene)ethane-1,2-diamine | 1422354-86-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (N1E,N2E)-N1,N2-bis(1-(pyrazin-2-yl)ethylidene)ethane-1,2-diamine
• 英文别名: (N¹E,N²E)-N¹,N²-bis(1-(pyrazin-2-yl)ethylidene)ethane-1,2-diamine
• CAS: 1422354-86-6
• 化学式: C₁₄H₁₆N₆
• 分子量: 268.321
• InChiKey: VABVUNXDJNXFDG-JYFOCSDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  76.28
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (N1E,N2E)-N1,N2-bis(1-(pyrazin-2-yl)ethylidene)ethane-1,2-diamine 、 silver nitrate 以 乙醇 为溶剂， 反应 3.0h， 以63%的产率得到bis(μ²-N,N′-bis((2-pyrazinyl)ethylidene)ethane-1,2-diamine-N,N′,N″,N″’′)-di-silver(I) dinitrate
  参考文献：
  名称：

  Synthesis, characterization and in vitro cytotoxic properties of new silver(I) complexes of two novel Schiff bases derived from thiazole and pyrazine

  摘要：

  Two new ethylenediamine Schiff bases of 2-acetylthiazole and 2-acetylpyrazine (abbreviated as Th-Th and Py-Py respectively), as well as their silver(I) complexes [Ag(Th-Th)](2)center dot 2(NO3) and [Ag(Py-Py)](2)center dot 2(NO3), have been prepared and characterized by a variety of physico-chemical techniques including elemental analyses, m.p., H-1 NMR, C-13 NMR, ESI-QTOF-MS, FT/IR, UV-Vis and theoretical calculations including density functional theory (DFT) and time dependent density functional theory (TD-DFT) methods. All structures were solved from single crystal X-ray diffraction (SXRD) data, except [Ag(Py-Py)](2)center dot 2(NO3), whose crystal is not good enough for SXRD. Hence, conventional powder X-ray diffraction (PXRD) has to be used. As a first step, the stoichiometric formula of [Ag(Py-Py)](2)center dot 2(NO3) was ascertained by elemental analyses and ESI-QTOF-MS. IR and UV-Vis indicated the existence of coordinated Py-Py and charge-balancing NO. On the basis of symmetry character proved by NMR, three possible symmetrical Ag(l) coordination structures were designed and optimized by DFT method. Then, relative binding free energies were calculated to find the most appropriate molecule structure. DFT results suggest that four imine-N and four ortho-ring-N atoms from two Py-Py ligands are coordinated to two Ag(I) ions, resulting in a similar dimer structure as that of [Ag(Th-Th)](2)center dot 2(NO3). The molecule structure was further confirmed by PXRD based crystal structure, which was solved following direct space method and refined by the Rietveld method. The antitumor activities of the Schiff bases and their silver(l) complexes have been evaluated against human lung cancer cell line A549. Both silver(I) complexes were found to display cytotoxicity (IC50 = 3.15 +/- 0.5 and 9.73 +/- 1.1 mu M) that is similar to or better than that of cisplatin, while metal-free Schiff bases show very low activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.01.014
• 作为产物：
  描述：

  2-乙酰基吡嗪 、 乙二胺 以 甲醇 为溶剂， 反应 8.0h， 以83%的产率得到(N1E,N2E)-N1,N2-bis(1-(pyrazin-2-yl)ethylidene)ethane-1,2-diamine
  参考文献：
  名称：

  Syntheses, crystal structures and antioxidant properties of four complexes derived from a new Schiff base ligand (N1E,N2E)-N1,N2-bis(1-(pyrazin-2-yl)ethylidene)ethane-1,2 diamine

  摘要：

  Four Ag(I), Cd(II) and Cu(II) complexes, [Ag2L2](ClO4)(2) (1), [CdL(NO3)(2)] (2), [Cd2L2Cl4] (3) and [Cu2L2(ClO4)(3)](ClO4) (4), derived from the new Schiff base ligand ((NE)-E-1,(NE)-E-2)-N-1,N-2-bis(1-(pyrazin-2-yl)ethylidene)ethane-1,2 diamine (L) have been synthesized and crystallographically characterized. The crystal structural features of 1-4 show that 1 is a ligand-supported dinuclear silver complex, 2 is a mononuclear eight-coordinate complex, 3 is a dinuclear hepta coordinate species and 4, interestingly, discloses two distinctly crystallographically independent groups of mononuclear [Cu(ClO4)(2)L] and a 1D [Cu(ClO4)L](ClO4) unit in one asymmetric group. Furthermore, pi center dot center dot center dot pi stacking and/or hydrogen bonding interactions seem to be effective in stabilizing these crystal structures. The antioxidant activities of L and complexes 1-4 have also been studied. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2013.11.021