3-(2-methoxyphenylamino)-1,2-propanediol | 57682-14-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(2-methoxyphenylamino)-1,2-propanediol
• 英文别名: N-o-Methoxyphenyl-2,3-dihydroxypropylamin；3-o-Anisidinopropan-1.2-diol；3-(2-Methoxyanilino)-1,2-propanediol；3-(2-methoxyanilino)propane-1,2-diol
• CAS: 57682-14-1
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: CYZWWNDOIPZOOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻甲氧基苯胺 、 3-氯-1,2-丙二醇 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以26%的产率得到3-(2-methoxyphenylamino)-1,2-propanediol
  参考文献：
  名称：

  Guaifenesin Derivatives Promote Neurite Outgrowth and Protect Diabetic Mice from Neuropathy

  摘要：

  In diabetic patients, an early index of peripheral neuropathy is the slowing of conduction velocity in large myelinated neurons and a lack of understanding of the basic pathogenic mechanisms hindered therapeutics development. Racemic (R/S)-guaifenesin (1) was identified as a potent enhancer of neurite outgrowth using an in vitro screen. Its R-enantiomer (R)-1 carried the most biological activity, whereas the S-enantiomer(S)-1 was inactive. Focused structural variations to (R/S)-1 was conducted to identify potentially essential groups for the neurite outgrowth activity. In vivo therapeutic studies indicated that both (R/S)-1 and (R)-1 partially prevented motor nerve conduction velocity slowing in a mouse model of type 1 diabetes. In vitro microsomal assays suggested that compounds (R)-1 and (5)-1 are not metabolized rapidly, and PAMPA assay indicated moderate permeability through the membrane Findings revealed here could lead to the development of novel drugs for diabetic neuropathy.

  DOI：

  10.1021/jm400401y

文献信息

• Guaifenesin Derivatives Promote Neurite Outgrowth and Protect Diabetic Mice from Neuropathy
  作者：Mallinath B. Hadimani、Meena K. Purohit、Chandrashaker Vanampally、Randy Van der Ploeg、Victor Arballo、Dwane Morrow、Katie E. Frizzi、Nigel A. Calcutt、Paul Fernyhough、Lakshmi P. Kotra

  DOI：10.1021/jm400401y

  日期：2013.6.27

  In diabetic patients, an early index of peripheral neuropathy is the slowing of conduction velocity in large myelinated neurons and a lack of understanding of the basic pathogenic mechanisms hindered therapeutics development. Racemic (R/S)-guaifenesin (1) was identified as a potent enhancer of neurite outgrowth using an in vitro screen. Its R-enantiomer (R)-1 carried the most biological activity, whereas the S-enantiomer(S)-1 was inactive. Focused structural variations to (R/S)-1 was conducted to identify potentially essential groups for the neurite outgrowth activity. In vivo therapeutic studies indicated that both (R/S)-1 and (R)-1 partially prevented motor nerve conduction velocity slowing in a mouse model of type 1 diabetes. In vitro microsomal assays suggested that compounds (R)-1 and (5)-1 are not metabolized rapidly, and PAMPA assay indicated moderate permeability through the membrane Findings revealed here could lead to the development of novel drugs for diabetic neuropathy.