(N¹E,N²E)-N¹,N²-bis(1-(1,3-thiazol-2-yl)ethylidene)-1,2-ethanediamine | 1417901-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (N¹E,N²E)-N¹,N²-bis(1-(1,3-thiazol-2-yl)ethylidene)-1,2-ethanediamine
• 英文别名: (N¹E,N²E)-N¹,N²-bis(1-(1,3-thiazol-2-yl)ethylidene)ethane-1,2-diamine
• CAS: 1417901-62-2
• 化学式: C₁₂H₁₄N₄S₂
• 分子量: 278.402
• InChiKey: AUPTXEBFFUJMJK-UTLPMFLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.5
• 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-(1,3-thiazol-2-yl)ethylidene)-1,2-ethanediamine 、 silver nitrate 以 乙醇 为溶剂， 生成 (N¹E,N²E)-N¹,N²-bis(1-(1,3-thiazol-2-yl)ethylidene)-1,2-ethanediamine silver nitrate
  参考文献：
  名称：

  一类含银的噻唑西弗碱配合物的结构、制备和 用途

  摘要：

  本发明涉及一类新化合物的结构、制备方法及用途。新化合物的分子式C12H14N4S2Ag+·X-（X-可为NO3-、Cl-、Br-、F-、I-等其他药学上可接受的阴离子），其中配阳离子的化学名为：(N1E,N2E)-N1,N2-二(1-(1,3-噻唑-2-基)亚乙基）-1,2-乙二胺合银配离子，配体(N1E,N2E)-N1,N2-二(1-(1,3-噻唑-2-基)亚乙基）-1,2-乙二胺的结构如下：。该配合物制备方法简单，纯度好，产率高，对肿瘤细胞有较高的毒性（优于顺铂），可以抑制癌细胞增殖，有希望成为一种高效、低毒的抗肿瘤药物。

  公开号：

  CN102936257B
• 作为产物：
  描述：

  2-乙酰基噻唑 、 乙二胺 以 乙醇 为溶剂， 反应 14.0h， 以81%的产率得到(N¹E,N²E)-N¹,N²-bis(1-(1,3-thiazol-2-yl)ethylidene)-1,2-ethanediamine
  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