2-methoxy-5-[(4-methoxyphenylimino)methyl]phenol | 24033-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-methoxy-5-[(4-methoxyphenylimino)methyl]phenol
• 英文别名: 2-Methoxy-5-[(4-methoxyphenyl)iminomethyl]phenol
• CAS: 24033-06-5
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: QSTXUICCRUWZHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methoxy-5-[(4-methoxyphenylimino)methyl]phenol 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 4-[3-(tert-butyldimethylsilanyloxy)-4-methoxyphenyl]-1-(4-methoxyphenyl)-3-phenoxyazetidin-2-one
  参考文献：
  名称：

  Synthesis and Biochemical Evaluation of 3-Phenoxy-1,4-diarylazetidin-2-ones as Tubulin-Targeting Antitumor Agents

  摘要：

  Structure-activity relationships for a series of 3-phenoxy-1,4-diarylazetidin-2-ones were investigated, leading to the discovery of a number of potent antiproliferative compounds, including trans-4-(3-hydroxy-4-methoxyphenyl)-3-phenoxy-1-(3,4,5-trimethoxyphenyl)azetidin-2-one (78b) and trans-4-(3-amino-4-methoxyphenyl)-3-phenoxy-1-(3,4,5-trimethoxyphenyl)azetidin-2-one (90b). X-ray crystallography studies indicate the potential importance of the torsional angle between the 1-phenyl A ring and 4-phenyl B ring for potent antiproliferative activity and that a trans configuration between the 3-phenoxy and 4-phenyl rings is generally optimal. These compounds displayed IC50 values of 38 and 19 nM, respectively, in MCF-7 breast cancer cells, inhibited the polymerization of isolated tubulin in vitro, disrupted the microtubular structure in MCF-7 cells as visualized by confocal microscopy, and caused G(2)/M arrest and apoptosis. Compound 90b possessed a mean GI50 value of 22 nM in the NCI60 cell line screen, displayed minimal cytotoxicity, and was shown to interact at the colchicine-binding site on beta-tubulin. Phosphate and amino acid prodrugs of both 78b and 90b were synthesized, of which the alanine amide 102b retained potency and is a promising candidate for further clinical development.

  DOI：

  10.1021/acs.jmedchem.5b01086
• 作为产物：
  描述：

  异香兰素 、 甲氧苯胺 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 以70%的产率得到2-methoxy-5-[(4-methoxyphenylimino)methyl]phenol
  参考文献：
  名称：

  Antileishmanial, Antimicrobial and Antifungal Activities of Some New Aryl Azomethines

  摘要：

  合成了一系列十八种腙，由适当的主要芳香胺与芳香和/或杂芳香羧醛反应得到。合成的腙已被评估其体外抗利什曼病、抗菌和抗真菌活性。结果显示大多数合成化合物具有一定的抗真菌活性，而抗利什曼病活性结果则突显所有合成腙均抑制寄生虫生长，其中大多数对利什曼ia major 前鞭毛体表现出高度的有效性。未观察到显著的杀菌活性。

  DOI：

  10.3390/molecules15020660