6-(羟甲基)-香豆素-3-羧酸 | 176770-22-2

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 6-(羟甲基)-香豆素-3-羧酸
• 英文名称: 6-(hydroxymethyl)-2-oxo-2H-1-benzopyran-3-carboxylic acid
• 英文别名: 6-hydroxymethyl-2-oxo-2H-1-benzopyrane-3-carboxylic acid；6-hydroxymethyl-2-oxo-2H-1-benzopyran-3-carboxylic acid；6-(hydroxymethyl)-2-oxo-2H-chromene-3-carboxylic acid；6-hydroxymethyl-2-oxo-2H-chromene-3-carboxylic acid；6-hydroxymethyl-2-oxo-2H-chromene-3-carboxylic acid；6-Hydroxymethyl-2-oxo-2H-chromen-3-carbonsaeure；6-(hydroxymethyl)-2-oxochromene-3-carboxylic acid
• CAS: 176770-22-2
• 化学式: C₁₁H₈O₅
• 分子量: 220.182
• InChiKey: AESUZZDVQZTHIN-UHFFFAOYSA-N

物化性质

• 熔点：
  223.5-225 °C
• 沸点：
  489.3±45.0 °C(Predicted)
• 密度：
  1.559±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(羟甲基)-香豆素-3-羧酸 在 吡啶 、 氯化亚砜 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 2-carboxyphenyl 6-(chloromethyl)-2-oxo-2H-1-benzopyran-3-carboxylate
  参考文献：
  名称：

  Toward the First Class of Suicide Inhibitors of Kallikreins Involved in Skin Diseases

  摘要：

  The inhibition of kallikreins 5 and 7, and possibly kallikrein 14 and matriptase, (that initiates the kallikrein proteolytic cascade) constitutes an innovative way to treat some skin diseases such as Netherton syndrome. We present here the inhibitory properties of coumarin-3-carboxylate derivatives against these enzymes. Our small collection of these versatile organic compounds was enriched by newly synthesized derivatives in order to obtain molecules selective against one, two, three enzymes or acting on the four ones. We evidenced a series of compounds with IC50 values in the nanomolar range. A suicide mechanism was observed against kallikrein 7 whereas the inactivation was either definitive (suicide type) or transient for kallikreins 5 and 14, and matriptase. Most of these potent inhibitors were devoid of cytotoxicity toward healthy human keratinocytes. In situ zymography investigations on skin sections from human kallikrein 5 transgenic mouse revealed significant reduction of the global proteolytic activity by several compounds.

  DOI：

  10.1021/jm500988d
• 作为产物：
  描述：

  2-羟基-5-(羟基甲基)苯甲醛 在 哌啶 、 水 、 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 17.18h， 生成