2-(((2-(1H-indol-3-yl)ethyl)imino)methyl)-4,6-di-tert-butylphenol | 1206139-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(((2-(1H-indol-3-yl)ethyl)imino)methyl)-4,6-di-tert-butylphenol
• 英文别名: 2-((2-(1H-indol-3-yl)ethylimino)methyl)-4,6-di-tert-butylphenol
• CAS: 1206139-67-4
• 化学式: C₂₅H₃₂N₂O
• 分子量: 376.542
• InChiKey: SUWNLVKOEUKIOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  48.38
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(((2-(1H-indol-3-yl)ethyl)imino)methyl)-4,6-di-tert-butylphenol 、 zinc(II) acetate dihydrate 在 triethyl amine 作用下， 以 乙醇 为溶剂， 以72%的产率得到
  参考文献：
  名称：

  Synthesis, structural characterization, and anti-ulcerogenic activity of schiff base ligands derived from tryptamine and 5-chloro, 5-nitro, 3,5-ditertiarybutyl salicylaldehyde and their nickel(II), copper(II), and zinc(II) complexes

  摘要：

  Ni(II), Cu(II), and Zn(II) complexes with bidentate Schiff bases derived from the condensation reaction of 5-chlorosalicylaidehyde, 5-nitrosalicylaldehyde, and 3,5 ditertiarybutyl-2-hydroxy benzaldehyde with tryptamine, have been reported. The ligands and complexes were characterized by elemental analysis, IR, H-1 NMR and UV-Vis spectroscopy as well as single crystal X-ray structure analysis whenever possible. The complexes were found to have the general formula [M(L)(2)]. Spectral studies reveal that these Schiff bases were acting as bidentate ligands and co-ordinating to the metal center through deprotonated phenolate oxygen and azomethine nitrogen atoms. The Zn(II) complexes establish a tetrahedral geometry in a 1:2 metal to ligand stoichiometry, whereas a square planar geometry was proposed for the nickel and copper complexes, slightly distorted in the case of the latter.The antiulcer activity of 5-chlorosalicylalclehyde derivative and its nickel and copper complexes were evaluated in ethanol-induced gastric mucosal injury in rats. This Schiff base and its complexes promote ulcer protection as ascertained by the comparative decrease in ulcer areas, and inhibition of edema and leucocyte infiltration of the submucosal layer. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2009.10.004
• 作为产物：
  描述：

  色胺 、 3,5-二叔丁基水杨醛 以 甲醇 为溶剂， 反应 24.0h， 以66%的产率得到2-(((2-(1H-indol-3-yl)ethyl)imino)methyl)-4,6-di-tert-butylphenol
  参考文献：
  名称：

  Schiff bases of tryptamine as potent inhibitors of nucleoside triphosphate diphosphohydrolases (NTPDases): Structure-activity relationship

  摘要：

  Overexpression of NTPDases leads to a number of pathological situations such as thrombosis, and cancer. Thus, effective inhibitors are required to combat these pathological situations. Different classes of NTPDase inhibitors are reported so far including nucleotides and their derivatives, sulfonated dyes such as reactive blue 2, suramin and its derivatives, and polyoxomatalates (POMs). Suramin is a well-known and potent NTPDase inhibitor, nonetheless, a range of side effects are also associated with it. Reactive blue 2 also had non-specific side effects that become apparent at high concentrations. In addition, most of the NTPDase inhibitors are high molecular weight compounds, always required tedious chemical steps to synthesize. Hence, there is still need to explore novel, low molecular weight, easy to synthesize, and potent NTPDase inhibitors.Keeping in mind the known NTPDase inhibitors with imine functionality and nitrogen heterocycles, Schiff bases of tryptamine, 1-26, were synthesized and characterized by spectroscopic techniques such as EI-MS, HREI-MS, H-1-, and C-13 NMR. All the synthetic compounds were evaluated for the inhibitory avidity against activities of three major isoforms of NTPDases: NTPDase-1, NTPDase-3, and NTPDase-8. Cumulatively, eighteen compounds were found to show potent inhibition (Ki = 0.0200-0.350 mu M) of NTPDase-1, twelve (Ki = 0.071-1.060 mu M) of NTPDase-3, and fifteen compounds inhibited (Ki = 0.0700-4.03 mu M) NTPDase-8 activity. As a comparison, the Kis of the standard inhibitor suramin were 1.260 +/- 0.007, 6.39 +/- 0.89 and 1.180 +/- 0.002 mu M, respectively. Kinetic studies were performed on lead compounds (6, 5, and 21) with human (h-) NTPDase-1, -3, and -8, and Lineweaver-Burk plot analysis showed that they were all competitive inhibitors. In silico study was conducted on compound 6 that showed the highest level of inhibition of NTPDase-1 to understand the binding mode in the active site of the enzyme.

  DOI：

  10.1016/j.bioorg.2018.10.046