(E)-4-chloro-2-(((4-hydroxyphenethyl)imino)methyl)phenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-4-chloro-2-(((4-hydroxyphenethyl)imino)methyl)phenol
• 化学式: C₁₅H₁₄ClNO₂
• 分子量: 275.735
• InChiKey: PHIZEIDSBDLSCC-LICLKQGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  52.82
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  对羟基苯乙胺 、 5-氯代水杨醛 以 甲醇 为溶剂， 反应 72.0h， 以90%的产率得到(E)-4-chloro-2-(((4-hydroxyphenethyl)imino)methyl)phenol
  参考文献：
  名称：

  Synthesis and antimicrobial activities of Schiff bases derived from 5-chloro-salicylaldehyde

  摘要：

  A series of Schiff bases (compounds 1-26) were synthesized by reacting 5-chloro-salicylaldehyde and primary amines, 15 (compounds 2-4, 6, 7, 10, 12-17, 23, 25 and 26) of which were first reported. The chemical structures of these compounds were confirmed by means of H-1 NMR, C-13 NMR, ESI-MS and elemental analyses. The compounds were assayed for antibacterial (Bacillus subtilis, Escherichia coli, Pseudomonas fluorescence and Staphylococcus aureus) and antifungal (Aspergillus niger, Candida albicans and Trichophyton rubrum) activities by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl trtrazolium bromide) method. Among the compounds tested, (E)-4-chloro-2-((4-fluorobenzylimino)methyl)phenol (2) showed the most favorable antimicrobial activity with MICs of 45.2, 1.6, 2.8, 3.4, and 47.5 mu g/mL against B. subtilis, E. coli, P. fluorescence, S. aureus and A. niger, respectively. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.11.010

文献信息

• Synthesis and antimicrobial activities of Schiff bases derived from 5-chloro-salicylaldehyde
  作者：Lei Shi、Hui-Ming Ge、Shu-Hua Tan、Huan-Qiu Li、Yong-Chun Song、Hai-Liang Zhu、Ren-Xiang Tan

  DOI：10.1016/j.ejmech.2006.11.010

  日期：2007.4

  A series of Schiff bases (compounds 1-26) were synthesized by reacting 5-chloro-salicylaldehyde and primary amines, 15 (compounds 2-4, 6, 7, 10, 12-17, 23, 25 and 26) of which were first reported. The chemical structures of these compounds were confirmed by means of H-1 NMR, C-13 NMR, ESI-MS and elemental analyses. The compounds were assayed for antibacterial (Bacillus subtilis, Escherichia coli, Pseudomonas fluorescence and Staphylococcus aureus) and antifungal (Aspergillus niger, Candida albicans and Trichophyton rubrum) activities by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl trtrazolium bromide) method. Among the compounds tested, (E)-4-chloro-2-((4-fluorobenzylimino)methyl)phenol (2) showed the most favorable antimicrobial activity with MICs of 45.2, 1.6, 2.8, 3.4, and 47.5 mu g/mL against B. subtilis, E. coli, P. fluorescence, S. aureus and A. niger, respectively. (c) 2006 Elsevier Masson SAS. All rights reserved.
• Ultrasonic synthesis of tyramine derivatives as novel inhibitors of <b>α</b>-glucosidase <i>in vitro</i>
  作者：Hina Siddiqui、Muhammad Arslan Bashir、Kulsoom Javaid、Arsalan Nizamani、Huma Bano、Sammer Yousuf、Atta-ur Rahman、M. Iqbal Choudhary

  DOI：10.3109/14756366.2016.1142983

  日期：2016.11.1

  Tyramine derivatives 3-27 were synthesized by using conventional and environmental friendly ultrasonic techniques. These derivatives were then evaluated for the first time for their a-glucosidase (Sources: Saccharomyces cerevisiae and mammalian rat-intestinal acetone powder) inhibitory activity by using in vitro mechanism-based biochemical assays. Compounds 7, 14, 20, 21 and 26 were found to be more active (IC50 = 49.7 +/- 0.4, 318.8 +/- 3.7, 23.5 +/- 0.9, 302.0 +/- 7.3 and 230.7 +/- 4.0 mu M, respectively) than the standard drug, acarbose (IC50 = 840.0 +/- 1.73 mu M (observed) and 780 +/- 0.028 mu M (reported)) against alpha-glucosidase obtained from Saccharomyces cerevisiae. Kinetic studies were carried out on the most active members of the series in order to determine their mode of inhibition and dissociation constants. Compounds 7, 20 and 26 were found to be the competitive inhibitors of alpha-glucosidase. These compounds were also screened for their protein antiglycation, and dipeptidyl peptidase-IV (DPP-IV) inhibitory activities. Only compounds 20, 22 and 27 showed weak antiglycation activity with IC50 values 505.27 +/- 5.95, 581.87 +/- 5.50 and 440.58 +/- 2.74 mu M, respectively. All the compounds were found to be inactive against DDP-IV enzyme. Inhibition of alpha-glucosidase, DPP-IV enzymes and glycation of proteins are valid targets for the discovery of antidiabetic drugs. Cytotoxicity of compounds 3-27 was also evaluated by using mouse fibroblast 3T3 cell lines. All the compounds were found to be noncytotoxic. The current study describes the synthesis alpha-glucosidase inhibitory activity of derivatives, based on a natural product tyramine template. The compounds reported here may serve as the starting point for the design and development of novel alpha-glucosidase inhibitors as antidiabetic agents.