5-hydroxymethyl-4-[(2-hydroxy-5-methyl-phenylimino)-methyl]-2-methyl-pyridin-3-ol | 25765-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 5-hydroxymethyl-4-[(2-hydroxy-5-methyl-phenylimino)-methyl]-2-methyl-pyridin-3-ol
• 英文别名: 2-Pyridoxylidenamino-4-methylphenol；5-(Hydroxymethyl)-4-[(2-hydroxy-5-methylphenyl)iminomethyl]-2-methylpyridin-3-ol
• CAS: 25765-12-2
• 化学式: C₁₅H₁₆N₂O₃
• 分子量: 272.304
• InChiKey: FJBUXELORIMJNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  85.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-hydroxymethyl-4-[(2-hydroxy-5-methyl-phenylimino)-methyl]-2-methyl-pyridin-3-ol 、 二丁基二氯化锡 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到Dibutyltin(2+);5-(hydroxymethyl)-2-methyl-4-[(5-methyl-2-oxidophenyl)iminomethyl]pyridin-3-olate
  参考文献：
  名称：

  Bioactive Penta-Coordinated Diorganotin(Iv) Complexes of Pyridoxalimine Schiff Bases

  摘要：

  Diorganotin(IV) complexes of an extended system derived from the condensation of pyridoxal hydrochloride with 2-amino phenol (H2L1), 2-amino-4-methyl phenol (H2L2), 2-amino-4-chloro phenol (H2L3), 2-amino-4-nitro phenol (H2L4), 1-amino-2-naphthol hydrochloride (H2L5) have been synthesized by the reaction of dichlorodiorganotin(IV) in a 1:1 molar ratio with these ligands. Spectral studies (IR, H-1, C-13, Sn-119 NMR) along with physical data evidenced the formation of penta-coordinated species with the ligands acting as tridentate (ONO) with oxygen occupying the axial positions, and nitrogen at one of the equatorial positions. The ligands and their organotin complexes have been evaluated for antimicrobial activity against phytopathogenic fungi Candida albicans and Aspergillus niger at 25 +/- 1 degrees C and bacteria Bacillus subtilis, Escherichia coli, and Staphylococcus aureus at 37 +/- 1 degrees C. The activities of the ligands have been enhanced on complexation and the results indicate that they exhibit significant antimicrobial properties.

  DOI：

  10.1080/10426507.2012.692129
• 作为产物：
  描述：

  、 邻氨基对甲苯酚 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 5-hydroxymethyl-4-[(2-hydroxy-5-methyl-phenylimino)-methyl]-2-methyl-pyridin-3-ol
  参考文献：
  名称：

  Bioactive Penta-Coordinated Diorganotin(Iv) Complexes of Pyridoxalimine Schiff Bases

  摘要：

  Diorganotin(IV) complexes of an extended system derived from the condensation of pyridoxal hydrochloride with 2-amino phenol (H2L1), 2-amino-4-methyl phenol (H2L2), 2-amino-4-chloro phenol (H2L3), 2-amino-4-nitro phenol (H2L4), 1-amino-2-naphthol hydrochloride (H2L5) have been synthesized by the reaction of dichlorodiorganotin(IV) in a 1:1 molar ratio with these ligands. Spectral studies (IR, H-1, C-13, Sn-119 NMR) along with physical data evidenced the formation of penta-coordinated species with the ligands acting as tridentate (ONO) with oxygen occupying the axial positions, and nitrogen at one of the equatorial positions. The ligands and their organotin complexes have been evaluated for antimicrobial activity against phytopathogenic fungi Candida albicans and Aspergillus niger at 25 +/- 1 degrees C and bacteria Bacillus subtilis, Escherichia coli, and Staphylococcus aureus at 37 +/- 1 degrees C. The activities of the ligands have been enhanced on complexation and the results indicate that they exhibit significant antimicrobial properties.

  DOI：

  10.1080/10426507.2012.692129

文献信息

• Schiff base Sn(IV) complexes as cytotoxic agents: Synthesis, structure, isosteric and bioisosteric replacement
  作者：José M. Galván-Hidalgo、Teresa Ramírez-Apan、Antonio Nieto-Camacho、Simón Hernández-Ortega、Elizabeth Gómez

  DOI：10.1016/j.jorganchem.2017.08.017

  日期：2017.10

  plane and the two oxygen atoms in the equatorial plane. Additionally, the in vitro cytotoxicity tests of the complexes towards six types of human cancerous cell lines U-251 (glioblastoma), K-562 (chronic myelogenous leukemia), HCT-15 (human colorectal), MCF-7 (human breast), MDA-MB-231(human breast) and SKLU-1 (non-small cell lung) showed the superior activity of the organotin complexes compared to the

  据报道，制备和表征了两个系列的有机锡（IV）配合物，每个系列在键合到锡原子（环己基或双（三甲基）甲硅烷基甲基）上的取代基的性质不同。等规和生物等规方法被用作分子设计的策略。配体是5-羟基甲基-4-[（2-羟基苯基）亚氨基甲基] -2-甲基吡啶-3-醇，在4位被甲基，卤代（F，Cl），甲氧基，硝基和叔丁基取代；取决于配体的性质，通过多组分策略以合理至高产率进行有机锡（IV）配合物的合成。所有新的配合物均通过IR，MS，X射线测定和NMR（1 H，13 C，119锡）。配合物的晶体学数据表明，金属锡中心周围采用的几何形状在2c的方形金字塔形和3b-3d的三角形双金字塔形之间变化，烷基在三角平面，两个氧原子在赤道平面。此外，该复合物对六种类型的人类癌细胞系U-251（胶质母细胞瘤），K-562（慢性粒细胞性白血病），HCT-15（人结肠直肠），MCF-7（人乳腺），与相应的顺铂用作阳性对照相比，