3,3'-(1,3-phenylenebis(azanylylidene)bis(1,7,7-trimethylbicyclo[2.2.1]heptan-2-one)) | 103226-85-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,3'-(1,3-phenylenebis(azanylylidene)bis(1,7,7-trimethylbicyclo[2.2.1]heptan-2-one))
• 英文别名: 1,7,7-Trimethyl-3-[3-[(4,7,7-trimethyl-3-oxo-2-bicyclo[2.2.1]heptanylidene)amino]phenyl]iminobicyclo[2.2.1]heptan-2-one
• CAS: 103226-85-3
• 化学式: C₂₆H₃₂N₂O₂
• 分子量: 404.552
• InChiKey: JEOYUQVLPUXKAF-UHFFFAOYSA-N

物化性质

• 沸点：
  529.5±60.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  58.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  copper(l) chloride 、 3,3'-(1,3-phenylenebis(azanylylidene)bis(1,7,7-trimethylbicyclo[2.2.1]heptan-2-one)) 以 四氢呋喃 为溶剂， 反应 18.0h， 以60%的产率得到
  参考文献：
  名称：

  Insight into the cytotoxicity of polynuclear Cu(I) camphor complexes

  摘要：

  Three new polynuclear Cu(I) camphor complexes, [(CuBr)(2){(p-H2NC6H4)NC10H14O}](n) (2d), [(CuCl)(4){m-C-6 H-4(NC10H14O)(2)}](n) (5f) and [(CuBr)(4){p-C6H4(NC10H14O)(2)}](n) (6e), were synthesized and their cytotoxicity, as well as that of the former reported compounds [(CuX)(2)(YNC10H14O)](n) (X = Cl : Y = NMe2 (1a), NH2 (1b), NHMe (1c), (H2NC6H4)NC10H14O (1d): X = Br; Y = NMe2 (2a)), [{Cu(Me2NNC10H14O)}(2)(mu-X)(2]) (X = Cl (3a), Br (4a)) and [(CuCl)(4){p-C6H4(NC10H14O)(2)}] (5f), were evaluated against the human colon adenocarcinoma cancer cell line HT29 using the colorimetric method (MU assay). The calculated IC50 values indicate that all the complexes have cytotoxic activity that ranges from high to moderate or low, depending on the characteristics of the camphor ligand and the halide co-ligand. The complexes [(CuCl)(4){m-C-6 H-4(NC10H14O)(2)}] (5f. IC50 = 32.0 + 1.1 mu M) and [(CuCl)(2)(H2NNC10H14O)](n) (1b, IC50 = 37.0 +/- 1.1 mu M) display the lowest IC50 values, while [(CuBr)(2){(p-H2NC6H4)NC10H14O}](n) (2d, IC50 = 119.9 +/- 1.1 mu M) displays the highest one. The IC50 value for 51 approaches that of cisplatin (26.3 + 1.1 mu M). No cytotoxic activity was detected for the camphor compounds H2NNC10H14O (b) and m-C6H4(NC10H14O)(2) (1), used as ligands. In selected cases, the copper accumulation in the cells was evaluated. No direct relationship was found between the copper uptake and the cytotoxicity of the complexes. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.11.020
• 作为产物：
  描述：

  樟脑醌 、 间苯二胺 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以91%的产率得到3,3'-(1,3-phenylenebis(azanylylidene)bis(1,7,7-trimethylbicyclo[2.2.1]heptan-2-one))
  参考文献：
  名称：

  Synthesis, characterization and study of the catalytic properties of Zn(II) camphor derived complexes

  摘要：

  Zinc(II) complexes of general formula [ZnX2(YNC10H14O)], [ZnX2(YNC10H13NSO2)], [ZnX2(H2NNC10H14O)(2)], [{ZnX2}(2)(YNC10H14O)] and [{ZnX2}(2)(YNC10H13NSO2)] were obtained from zinc halides (chloride or bromide) by reaction with the suitable camphor ligands.In most of the complexes, the camphor ligands remain unchanged upon coordination, except in [{Zn(MeNNC10H14O)}(2)(mu-Cl)(2)] where proton loss from MeHNNC10H14O occurs. The new complexes and camphor derivatives were characterized by IR, NMR (H-1, C-13{H}, DEPT, 2D) and elemental analysis. In some cases the surface composition was studied by X-ray photoelectron spectroscopy (XPS) and imaged by Scanning Electron Microscopy (SEM). Images of [ZnCl2(Me2NNC10H14O)] and [ZnCl2(Me2NNC10H13NSO2)] obtained by SEM show the solid particles have tubular structures capped in one or both extremities. The coordination of THF in [ZnCl2(YNC10H14O) THF] was confirmed by X-ray diffraction analysis. The camphor derivatives YNC10H14NSO2 (Y = NMe2; NHMe) and p-C6H4(NC10H14O)(2) were structurally characterized by X-ray diffraction analysis.The ability of selected Zn(II) camphor complexes to catalyse the cyclization of 4-pentyn-1-ol was evaluated showing that the binuclear complex [{ZnX2}(2)(YNC10H14O)] performs better than the mononuclear Zn(II) complexes. (C) 2013 Elsevier B.V. All rights reserve.

  DOI：

  10.1016/j.jorganchem.2013.10.040

文献信息

• Synthesis and Characterization of Camphorimine Au(I) Complexes with a Remarkably High Antibacterial Activity towards B. contaminans and P. aeruginosa
  作者：Joana P. Costa、Sílvia A. Sousa、Catarina Soeiro、Jorge H. Leitão、Adelino M. Galvão、Fernanda Marques、M. Fernanda N. N. Carvalho

  DOI：10.3390/antibiotics10101272

  日期：——

  Fourteen new camphorimine Au(I) complexes were synthesized and characterized by spectroscopic (NMR, FTIR) and elemental analysis. The structural arrangement of three selected examples were computed by Density Functional Theory (DFT) showing that the complexes essentially keep the AuI-CN} unit. The Minimum Inhibition Concentrations (MIC) were assessed for all complexes showing that they are active towards the Gram-negative strains E. coli ATCC25922, P. aeruginosa 477, and B. contaminans IST408 and the Gram-positive strain S. aureus Newman. The complexes display very high activity towards P. aeruginosa 477 and B. contaminans IST408 with selectivity towards B. contaminans. An inverse correlation between the MIC values and the gold content was found for B. contaminans and P. aeruginosa. However, plots of MIC values and Au content for P. aeruginosa 477 and B. contaminans IST408 follow distinct trends. No clear relationship could be established between the MIC values and the redox potentials of the complexes measured by cyclic voltammetry. The MIC values are essentially independent of the redox potentials either cathodic or anodic. The complexes K3[Au(CN)2}3(A4L)] (8, Y = m-OHC6H4) and K3[Au(CN)2}3(B2L)]·3H2O (14, Z = p-C6H4) display the lower MIC values for the two strains. In normal fibroblast cells, the IC50 values for the complexes are ca. one order of magnitude lower than their MIC values, although higher than that of the precursor KAu(CN)2.

  合成了14个新的松香胺Au(I)配合物，并通过光谱学（NMR，FTIR）和元素分析进行了表征。通过密度泛函理论（DFT）计算，选取了三个样品的结构排列，显示配合物基本保持AuI-CN}单元。评估了所有配合物的最小抑菌浓度（MIC），显示它们对革兰氏阴性菌E. coli ATCC25922、P. aeruginosa 477和B. contaminans IST408以及革兰氏阳性菌S. aureus Newman都具有活性。配合物对P. aeruginosa 477和B. contaminans IST408表现出非常高的活性，对B. contaminans具有选择性。对于B. contaminans和P. aeruginosa，MIC值与金含量呈反相关。然而，对于P. aeruginosa 477和B. contaminans IST408的MIC值和金含量的图表遵循不同的趋势。通过循环伏安法测量的配合物的氧化还原电位与MIC值之间没有明显的关系。MIC值无论是阴极还是阳极电位都基本独立。配合物K3[Au(CN)2}3(A4L)]（8，Y = m-OH ）和K3[Au(CN)2}3(B2L)]·3H2O（14，Z = p-C6H4）对两种菌株的MIC值较低。在正常成纤维细胞中，配合物的IC50值约比它们的MIC值低一个数量级，但高于前体KAu(CN)2的IC50值。