3-(5,7-dihydroxy-4-methyl-2-oxo-2H-chromen-3-yl)-propionic acid | 5852-05-1

• 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
• 英文名称: 3-(5,7-dihydroxy-4-methyl-2-oxo-2H-chromen-3-yl)-propionic acid
• 英文别名: 3-(5,7-Dihydroxy-4-methyl-2-oxo-2H-chromen-3-yl)-propionsaeure；3-(5,7-Dihydroxy-4-methyl-2-oxochromen-3-yl)propanoic acid；3-(5,7-dihydroxy-4-methyl-2-oxochromen-3-yl)propanoic acid
• CAS: 5852-05-1
• 化学式: C₁₃H₁₂O₆
• 分子量: 264.235
• InChiKey: CZQSWVLKGABSPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 3-(5,7-dihydroxy-4-methyl-2-oxo-2H-chromen-3-yl)-propionic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以79%的产率得到5,7-dihydroxy-4-methyl-3-(3-(4-methylpiperazin-1-yl)-3-oxopropyl)-2H-chromen-2-one
  参考文献：
  名称：

  Coumarin derivatives protect against ischemic brain injury in rats

  摘要：

  Neuroprotection strategies are of great importance in the treatment of ischemic brain injury. Screening of our in-stock coumarin derivatives identified compound 1 as exhibiting neuroprotective activity. Subsequently, a structural optimization was carried out, which led to the discovery of the potent compound 20. This compound significantly attenuated the damage in a cell line derived from a pheochromocytoma of the rat adrenal medulla induced by oxygen glucose deprivation in vitro. Furthermore, compound 20 exhibited clear neuroprotection in middle cerebral artery occlusion rats by reducing infarct size and brain-water content, improving neurological function, and suppressing neuronal loss and neuropathological changes in the cortex and hippocampus. Pharmacokinetic evaluation indicated that compound 20 could penetrate the blood brain barrier of rats. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.015
• 作为产物：
  描述：

  乙酰戊二酸二乙酯 在 盐酸 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 3.0h， 生成 3-(5,7-dihydroxy-4-methyl-2-oxo-2H-chromen-3-yl)-propionic acid
  参考文献：
  名称：

  Coumarin derivatives protect against ischemic brain injury in rats

  摘要：

  Neuroprotection strategies are of great importance in the treatment of ischemic brain injury. Screening of our in-stock coumarin derivatives identified compound 1 as exhibiting neuroprotective activity. Subsequently, a structural optimization was carried out, which led to the discovery of the potent compound 20. This compound significantly attenuated the damage in a cell line derived from a pheochromocytoma of the rat adrenal medulla induced by oxygen glucose deprivation in vitro. Furthermore, compound 20 exhibited clear neuroprotection in middle cerebral artery occlusion rats by reducing infarct size and brain-water content, improving neurological function, and suppressing neuronal loss and neuropathological changes in the cortex and hippocampus. Pharmacokinetic evaluation indicated that compound 20 could penetrate the blood brain barrier of rats. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.015

文献信息

• Shah; Shah, Chemische Berichte, 1938, vol. 71, p. 2075,2079
  作者：Shah、Shah

  DOI：——

  日期：——
• NOUVEAUX SUBSTRATS ENZYMATIQUES DERIVES DE PHENOXAZINONE ET LEUR UTILISATION COMME REVELATEUR DANS LA DETECTION DE MICROORGANISMES A ACTIVITE PEPTIDASE
  申请人：BIOMERIEUX

  公开号：EP1625117B1

  公开（公告）日：2008-01-09
• Coumarin derivatives protect against ischemic brain injury in rats
  作者：Mingna Sun、Jinfeng Hu、Xiuyun Song、Donghui Wu、Linglei Kong、Yupeng Sun、Dongmei Wang、Yan Wang、Naihong Chen、Gang Liu

  DOI：10.1016/j.ejmech.2013.04.015

  日期：2013.9

  Neuroprotection strategies are of great importance in the treatment of ischemic brain injury. Screening of our in-stock coumarin derivatives identified compound 1 as exhibiting neuroprotective activity. Subsequently, a structural optimization was carried out, which led to the discovery of the potent compound 20. This compound significantly attenuated the damage in a cell line derived from a pheochromocytoma of the rat adrenal medulla induced by oxygen glucose deprivation in vitro. Furthermore, compound 20 exhibited clear neuroprotection in middle cerebral artery occlusion rats by reducing infarct size and brain-water content, improving neurological function, and suppressing neuronal loss and neuropathological changes in the cortex and hippocampus. Pharmacokinetic evaluation indicated that compound 20 could penetrate the blood brain barrier of rats. (C) 2013 Elsevier Masson SAS. All rights reserved.