bis-(-2-oxo-bornyliden-(3))-p-phenylenediamine | 6326-63-2

• 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: bis-(-2-oxo-bornyliden-(3))-p-phenylenediamine
• 英文别名: Bis-(-2-oxo-bornyliden-(3))-p-phenylendiamin；3,3'-p-Phenylendiimino-bis-bornan-2-on；p-Phenylen-bis-；(+/-)-p-Phenylen-bis-iminocampher；1,7,7-Trimethyl-3-[4-[(4,7,7-trimethyl-3-oxo-2-bicyclo[2.2.1]heptanylidene)amino]phenyl]iminobicyclo[2.2.1]heptan-2-one
• CAS: 6326-63-2
• 化学式: C₂₆H₃₂N₂O₂
• 分子量: 404.552
• InChiKey: SCDLLHGZJNONCR-UHFFFAOYSA-N

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：

  bis-(-2-oxo-bornyliden-(3))-p-phenylenediamine 生成 p-Phenylen-bis-(amino-dl-campher)
  参考文献：
  名称：

  Singh; Bhaduri, Journal of the Indian Chemical Society, 1930, vol. 7, p. 545,560

  摘要：

  DOI：
• 作为产物：
  描述：

  樟脑醌 、 对苯二胺盐酸盐 在 sodium acetate 作用下， 生成 bis-(-2-oxo-bornyliden-(3))-p-phenylenediamine
  参考文献：
  名称：

  Singh; Bhaduri, Journal of the Indian Chemical Society, 1930, vol. 7, p. 545,560

  摘要：

  DOI：

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-OHC6H4）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。
• Tuning the Biological Activity of Camphorimine Complexes through Metal Selection
  作者：Joana P. Costa、Teresa Pinheiro、Maria S. Martins、M. Fernanda N. N. Carvalho、Joana R. Feliciano、Jorge H. Leitão、Rafaela A. L. Silva、Joana F. Guerreiro、Luís M. C. Alves、Inês Custódio、João Cruz、Fernanda Marques

  DOI：10.3390/antibiotics11081010

  日期：——

  four sets of camphorimine complexes based on the Cu(I), Cu(II), Ag(I), and Au(I) metal sites were assessed against the cisplatin-sensitive A2780 and OVCAR3 ovarian cancer cells. The results showed that the gold complexes were ca. one order of magnitude more active than the silver complexes, which in turn were ca. one order of magnitude more active than the copper complexes. An important finding was

  针对顺铂敏感的 A2780 和 OVCAR3 卵巢癌细胞评估了基于 Cu(I)、Cu(II)、Ag(I) 和 Au(I) 金属位点的四组樟脑胺复合物的细胞毒活性。结果表明，金配合物约为。比银络合物活性高一个数量级，而银络合物的活性大约是 ca。比铜络合物活性高一个数量级。一个重要的发现是 Ag(I) 和 Au(I) 樟脑胺复合物的细胞毒活性高于顺铂。另一个相关方面是樟脑胺复合物与 DNA 没有显着相互作用，与顺铂相反。正如 PIXE（粒子诱导的 X 射线发射）所确定的，樟脑胺复合物的细胞毒活性与 OVCAR3 细胞的细胞摄取有直接关系。通过循环伏安法评估，ROS（活性氧）形成的水平与具有相同金属的配合物的还原电位呈反比关系。为了深入了解复合物的毒性，评估了它们对非肿瘤细胞（HDF 和 V79 成纤维细胞）的细胞毒性。复合物的体内细胞毒性5使用线虫秀丽隐杆线虫也进行了评估。银樟脑胺复合物显示出最高的选择性系数（活性与毒性）。
• Forster; Thornley, Journal of the Chemical Society, 1909, vol. 95, p. 954
  作者：Forster、Thornley

  DOI：——

  日期：——
• Insight into the cytotoxicity of polynuclear Cu(I) camphor complexes
  作者：Tiago A. Fernandes、Filipa Mendes、Alexandra P.S. Roseiro、Isabel Santos、M. Fernanda N.N. Carvalho

  DOI：10.1016/j.poly.2014.11.020

  日期：2015.2

  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.
• Singh; Bhaduri, Journal of the Indian Chemical Society, 1930, vol. 7, p. 545,560
  作者：Singh、Bhaduri

  DOI：——

  日期：——