2,6-dimethyl-3-hydroxy-4-pyridinecarboxylic acid | 4328-87-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,6-dimethyl-3-hydroxy-4-pyridinecarboxylic acid
• 英文别名: 3-hydroxy-2,6-dimethylpyridine-4-carboxylic acid；3-hydroxy-2,6-dimethyl-isonicotinic acid；2,6-Dimethyl-3-hydroxyisonicotinic acid；3-Hydroxy-2,6-dimethylisonicotinic acid
• CAS: 4328-87-4
• 化学式: C₈H₉NO₃
• mdl: MFCD18803451
• 分子量: 167.164
• InChiKey: HMUZXOCYGAVFIY-UHFFFAOYSA-N

物化性质

• 熔点：
  294-295 °C(Solv: benzene (71-43-2))
• 沸点：
  470.0±45.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  70.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-3-hydroxy-4-pyridinecarboxylic acid 在 盐酸 、 双氧水 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Evaluation of 1,2-dimethyl-3-hydroxy-4-pyridinecarboxylic acid and of other 3-hydroxy-4-pyridinecarboxylic acid derivatives for possible application in iron and aluminium chelation therapy

  摘要：

  Four new possible chelating agents for iron and aluminium, 1,2-dimethyl-3-hydroxy-4-pyridinecarboxylic acid (DT712), 3-hydroxy-1,2,6-trimethyl-4-pyridinecarboxylic acid, 2,6-dimethyl-3-hydroxy-4-pyridinecarboxylic acid, and 2-ethyl-3-hydroxy-1-methyl-4-pyridinecarboxylic acid, were synthesized, and their complex formation with Fe(III) and Al(III) was studied by potentiometry, UV-Vis, H-1 NMR, and electrospray mass spectrometry (ESI-MS). Number, stoichiometry, and stability constants of metal-ligand complexes were obtained at 25 C in aqueous (Na)Cl 0.6 m. DT712 is the most promising hydroxypyridinecarboxylic acid considered so far for iron chelation therapy, as it forms the strongest Fe(III) complexes. This compound was further investigated to better clarify its possible behaviour in vivo with particular respect to iron chelation therapy. UV-Vis measurements were performed to determine the kinetics by which DT712 extracts Fe(III) from transferrin. DT712 resulted to have better kinetic properties than existing iron chelators. Ternary metal/DT712/citric acid complexes were studied by ESI-MS to check the competition with a typical low molecular weight ligand in the blood. The formation of only binary Fe(III)/ DT712 and Al(III)/DT712 complexes (and ternary complexes in aged solutions), suggests that DT712 effectively compete with citric acid in the metal complexation. Standard reduction potentials of Fe(III)/DT712 complexes, and the kinetic constants of complex formation, were obtained by cyclic voltammetiy. Accordingly, no redox cycling is expected to occur at in vivo conditions, and Fe(III)/DT712 complex formation should not be kinetically limited. On the basis of the present results, DT712 is proposed as candidate for iron chelation therapy. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2013.10.007
• 作为产物：
  描述：

  2-乙酰氨基丙酸乙酯 在 四磷十氧化物 、 magnesium oxide 作用下， 以 氯仿 为溶剂， 反应 20.5h， 生成 2,6-dimethyl-3-hydroxy-4-pyridinecarboxylic acid
  参考文献：
  名称：

  Evaluation of 1,2-dimethyl-3-hydroxy-4-pyridinecarboxylic acid and of other 3-hydroxy-4-pyridinecarboxylic acid derivatives for possible application in iron and aluminium chelation therapy

  摘要：

  Four new possible chelating agents for iron and aluminium, 1,2-dimethyl-3-hydroxy-4-pyridinecarboxylic acid (DT712), 3-hydroxy-1,2,6-trimethyl-4-pyridinecarboxylic acid, 2,6-dimethyl-3-hydroxy-4-pyridinecarboxylic acid, and 2-ethyl-3-hydroxy-1-methyl-4-pyridinecarboxylic acid, were synthesized, and their complex formation with Fe(III) and Al(III) was studied by potentiometry, UV-Vis, H-1 NMR, and electrospray mass spectrometry (ESI-MS). Number, stoichiometry, and stability constants of metal-ligand complexes were obtained at 25 C in aqueous (Na)Cl 0.6 m. DT712 is the most promising hydroxypyridinecarboxylic acid considered so far for iron chelation therapy, as it forms the strongest Fe(III) complexes. This compound was further investigated to better clarify its possible behaviour in vivo with particular respect to iron chelation therapy. UV-Vis measurements were performed to determine the kinetics by which DT712 extracts Fe(III) from transferrin. DT712 resulted to have better kinetic properties than existing iron chelators. Ternary metal/DT712/citric acid complexes were studied by ESI-MS to check the competition with a typical low molecular weight ligand in the blood. The formation of only binary Fe(III)/ DT712 and Al(III)/DT712 complexes (and ternary complexes in aged solutions), suggests that DT712 effectively compete with citric acid in the metal complexation. Standard reduction potentials of Fe(III)/DT712 complexes, and the kinetic constants of complex formation, were obtained by cyclic voltammetiy. Accordingly, no redox cycling is expected to occur at in vivo conditions, and Fe(III)/DT712 complex formation should not be kinetically limited. On the basis of the present results, DT712 is proposed as candidate for iron chelation therapy. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2013.10.007

文献信息

• One-pot synthesis of pyridine derivatives via diels-alder reactions of 2,4-dimethyl-5-methoxyoxazole
  作者：Samir Bondock

  DOI：10.1002/hc.20064

  日期：——

  A novel series of pyridine derivatives with anticipated biological activity have been synthesized via Diels-Alder reactions of 2,4-dimethyl-5-methoxyoxazole with different types of dienophiles. The regioselectivity of the cycloaddition was inverted from methylacrylate to tert-butylacrylate. The structural elucidation of the new compounds was carried on the basis of spectral and X-ray analyses. © 2005

  通过 2,4-二甲基-5-甲氧基恶唑与不同类型的亲二烯体的 Diels-Alder 反应合成了一系列具有预期生物活性的新型吡啶衍生物。环加成的区域选择性从丙烯酸甲酯反转为丙烯酸叔丁酯。新化合物的结构解析是在光谱和 X 射线分析的基础上进行的。© 2005 Wiley Periodicals, Inc. 杂原子化学 16:49–55, 2005; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20064