(E)-3-((4-methoxyphenylimino)methyl)benzene-1,2-diol | 111279-00-6

• 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: (E)-3-((4-methoxyphenylimino)methyl)benzene-1,2-diol
• 英文别名: 3-(((4-methoxyphenyl)imino)methyl)benzene-1,2-diol；3-[(4-Methoxyphenyl)iminomethyl]benzene-1,2-diol
• CAS: 111279-00-6
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: VHFKMUWSCDRBOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methanol;tribromoruthenium;triphenylarsane 、 (E)-3-((4-methoxyphenylimino)methyl)benzene-1,2-diol 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Schiff base complexes of ruthenium(III), molybdenum(VI) and uranium(VI), and use of the former as catalytic organic oxidants

  摘要：

  The new complexes [RuIIIX2(AsPh3)2(HL)] (X = Cl, Br; HL = monoanions of Schiff bases formed from condensation of 2,3-dihydroxybenzaldehyde and aniline or its omicron- and p-substituted derivatives), cis-[MoO2(HL)2] and trans-[UO2(HL)2.nH2O] (n = 0 or 2) have been isolated. They were characterized by spectroscopic techniques and investigated by cyclic voltammetry. The ruthenium(III) complexes were found to be effective catalysts for oxidation of primary alcohols to aldehydes, secondary alcohols to ketones and 3,5-di(tert-butyl)catechol to the corresponding omicron-benzoquinone in the presence of N-methyl-morpholine-N-oxide as co-oxidant.

  DOI：

  10.1016/s0277-5387(00)83299-4
• 作为产物：
  描述：

  2,3-二羟基苯甲醛 、 甲氧苯胺 以 甲醇 为溶剂， 反应 3.0h， 生成 (E)-3-((4-methoxyphenylimino)methyl)benzene-1,2-diol
  参考文献：
  名称：

  N-亚苄基苯胺衍生物作为潜在的TLR2抑制剂的合成，构效关系及初步机理研究

  摘要：

  Toll样受体2（TLR2）可以识别病原体相关的分子模式以防御入侵的生物，并且已成为有吸引力的治疗靶标。直到今天，还没有在临床试验中开发出TLR2小分子拮抗剂。本文中，我们借助CADD设计并合成了50种 N-苄叉基苯胺化合物。随后进行的体外研究产生了对TLR2具有最强抑制活性的优化化合物SMU-A0B13（IC 50= 18.21±0.87μM）。初步的机制研究表明，该TLR2抑制剂可通过NF-κB信号通路发挥高特异性和低毒性的作用，并且还可以有效下调HEK-blue hTLR2，人PBMC和SHE中的炎性细胞因子，例如SEAP，TNF-α和NO。原始的264.7细胞系。此外，对接情况还表明SMU-A0B13可以很好地与TLR2-TIR（PDB：1FYW）活性域结合，这可能解释了其生物活性。

  DOI：

  10.1016/j.bmc.2018.03.001

文献信息

• Palladium salicylaldimine complexes derived from 2,3-dihydroxybenzaldehyde
  作者：Eric G. Bowes、Graham M. Lee、Christopher M. Vogels、Andreas Decken、Stephen A. Westcott

  DOI：10.1016/j.ica.2011.07.051

  日期：2011.11

  Schiff bases derived from condensation of 2,3-dihydroxybenzaldehyde with various primary amines, such as 1-adamantanamine hydrochloride, 2,6-dimethylaniline, 2,6-diethylaniline and 2,6-diisopropylaniline, react with palladium(II) acetate to give the corresponding bis(N-arylsalicylaldiminato)palladium(II) complexes. These complexes have been found to be active catalyst precursors for the Suzuki-Miyaura cross-coupling of aryl bromides and iodides with aryl boronic acids using water as a solvent. (C) 2011 Elsevier B. V. All rights reserved.
• Synthesis, structure-activity relationships and preliminary mechanism study of N-benzylideneaniline derivatives as potential TLR2 inhibitors
  作者：Shaoyi Cai、Gengzheng Zhu、Xiaohong Cen、Jingjie Bi、Jingru Zhang、Xiaoshan Tang、Kun Chen、Kui Cheng

  DOI：10.1016/j.bmc.2018.03.001

  日期：2018.5

  we designed and synthesized 50 N-benzylideneaniline compounds with the help of CADD. And subsequent in vitro studies leading to the optimized compound SMU-A0B13 with most potent inhibitory activity to TLR2 (IC50=18.21 ± 0.87 μM). Preliminary mechanism studies indicated that this TLR2 inhibitor can work through the NF-κB signaling pathway with high specificity and low toxicity, and can also efficiently

  Toll样受体2（TLR2）可以识别病原体相关的分子模式以防御入侵的生物，并且已成为有吸引力的治疗靶标。直到今天，还没有在临床试验中开发出TLR2小分子拮抗剂。本文中，我们借助CADD设计并合成了50种 N-苄叉基苯胺化合物。随后进行的体外研究产生了对TLR2具有最强抑制活性的优化化合物SMU-A0B13（IC 50= 18.21±0.87μM）。初步的机制研究表明，该TLR2抑制剂可通过NF-κB信号通路发挥高特异性和低毒性的作用，并且还可以有效下调HEK-blue hTLR2，人PBMC和SHE中的炎性细胞因子，例如SEAP，TNF-α和NO。原始的264.7细胞系。此外，对接情况还表明SMU-A0B13可以很好地与TLR2-TIR（PDB：1FYW）活性域结合，这可能解释了其生物活性。
• Schiff base complexes of ruthenium(III), molybdenum(VI) and uranium(VI), and use of the former as catalytic organic oxidants
  作者：Ahmed M. El-Hendawy、Abd El-Ghany El-Kourashy、Mai M. Shanab

  DOI：10.1016/s0277-5387(00)83299-4

  日期：1992.1

  The new complexes [RuIIIX2(AsPh3)2(HL)] (X = Cl, Br; HL = monoanions of Schiff bases formed from condensation of 2,3-dihydroxybenzaldehyde and aniline or its omicron- and p-substituted derivatives), cis-[MoO2(HL)2] and trans-[UO2(HL)2.nH2O] (n = 0 or 2) have been isolated. They were characterized by spectroscopic techniques and investigated by cyclic voltammetry. The ruthenium(III) complexes were found to be effective catalysts for oxidation of primary alcohols to aldehydes, secondary alcohols to ketones and 3,5-di(tert-butyl)catechol to the corresponding omicron-benzoquinone in the presence of N-methyl-morpholine-N-oxide as co-oxidant.