(2S)-2-(3,8-二甲基薁-5-基)丙酸 | 489-87-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (2S)-2-(3,8-二甲基薁-5-基)丙酸
• 中文别名: 香豆素-7-频哪醇硼酸酯
• 英文名称: (Ξ)-2-(3,8-dimethyl-azulen-5-yl)-propionic acid
• 英文别名: (Ξ)-2-(3,8-Dimethyl-azulen-5-yl)-propionsaeure；(2S)-2-(3,8-dimethylazulen-5-yl)propanoic acid
• CAS: 489-87-2
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: VEHBLYQIKWPOQM-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-(3,8-二甲基薁-5-基)丙酸 以 重水 为溶剂， 生成 母菊薁
  参考文献：
  名称：

  Chamazulene Carboxylic Acid and Matricin:  A Natural Profen and Its Natural Prodrug, Identified through Similarity to Synthetic Drug Substances

  摘要：

  Chamazulene carboxylic acid ( 1) is a natural profen with anti-inflammatory activity and a degradation product of proazulenic sesquiterpene lactones, e. g., matricin. Both 1 and proazulenes occur in chamomile ( Matricaria recutita), yarrow ( Achillea millefolium), and a few other Asteraceae species. It was isolated in improved yields, characterized physicochemically, and found to be an inhibitor of cyclooxygenase-2, but not of cyclooxygenase-1. It had anti-inflammatory activity in several animal models with local and systemic application. When human volunteers were given matricin orally, plasma levels of 1 were found to be in the micromolar range. Matricin was converted to 1 in artificial gastric fluid, but not in artificial intestinal fluid. Matricin and the yarrow proazulenes are proposed to be anti-inflammatory through conversion to 1. Intriguingly, the biological activity of the natural compound 1 was found because of its similarity to fully synthetic drug substances. This is the reverse process of the common lead function of natural compounds in drug discovery.

  DOI：

  10.1021/np0601556
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 溶剂黄146 作用下， 生成 (2S)-2-(3,8-二甲基薁-5-基)丙酸
  参考文献：
  名称：

  Cekan et al., Collection of Czechoslovak Chemical Communications, 1954, vol. 19, p. 798,800

  摘要：

  DOI：

文献信息

• Chamazulene Carboxylic Acid and Matricin:  A Natural Profen and Its Natural Prodrug, Identified through Similarity to Synthetic Drug Substances
  作者：Mai Ramadan、Susanne Goeters、Bernhard Watzer、Eva Krause、Klaus Lohmann、Rudolf Bauer、Bernd Hempel、Peter Imming

  DOI：10.1021/np0601556

  日期：2006.7.1

  Chamazulene carboxylic acid ( 1) is a natural profen with anti-inflammatory activity and a degradation product of proazulenic sesquiterpene lactones, e. g., matricin. Both 1 and proazulenes occur in chamomile ( Matricaria recutita), yarrow ( Achillea millefolium), and a few other Asteraceae species. It was isolated in improved yields, characterized physicochemically, and found to be an inhibitor of cyclooxygenase-2, but not of cyclooxygenase-1. It had anti-inflammatory activity in several animal models with local and systemic application. When human volunteers were given matricin orally, plasma levels of 1 were found to be in the micromolar range. Matricin was converted to 1 in artificial gastric fluid, but not in artificial intestinal fluid. Matricin and the yarrow proazulenes are proposed to be anti-inflammatory through conversion to 1. Intriguingly, the biological activity of the natural compound 1 was found because of its similarity to fully synthetic drug substances. This is the reverse process of the common lead function of natural compounds in drug discovery.
• Cekan et al., Collection of Czechoslovak Chemical Communications, 1954, vol. 19, p. 798,800
  作者：Cekan et al.

  DOI：——

  日期：——