(2R)-2-[(1R)-1,2-dihydroxyethyl]-4-octadecoxy-3-phenylmethoxy-2H-furan-5-one | 107706-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (2R)-2-[(1R)-1,2-dihydroxyethyl]-4-octadecoxy-3-phenylmethoxy-2H-furan-5-one
• CAS: 107706-92-3
• 化学式: C₃₁H₅₀O₆
• 分子量: 518.734
• InChiKey: SAZWNRKPPNMWPC-VSGBNLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  37
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(1R)-1,2-dihydroxyethyl]-4-octadecoxy-3-phenylmethoxy-2H-furan-5-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以80%的产率得到2-O-octadecylisoascorbic acid
  参考文献：
  名称：

  Studies on scavengers of active oxygen species. 1. Synthesis and biological activity of 2-O-alkylascorbic acids

  摘要：

  A novel series of 2-O-alkylascorbic acids (5a-u) was synthesized, and their scavenging activities against active oxygen species as well as their suppressive effects on the arrhythmias in rat heart ischemia-reperfusion models were evaluated. Some 2-O-alkylascorbic acids (5e-1) exhibited potent inhibiting activities against lipid peroxidation in rat brain homogenates and in alleviating effects in the ischemia-reperfusion models. Studies on the structure-activity relationship demonstrated that a free 3-enolic hydroxyl group and the longer alkyl chains substituted on the 2-hydroxyl group of ascorbic acid were beneficial for the biological and pharmacological activities. 2-O-Octadecylascorbic acid (5k, CV-3611), one of the most potent and promising compounds, markedly inhibited lipid peroxidation (IC50 = 4.3 X 10(-6) M) and alleviated myocardial lesions induced by ischemia-reperfusion at an oral dose of 1 mg/kg in rats.

  DOI：

  10.1021/jm00399a019
• 作为产物：
  描述：

  Erythorbic acid 在 potassium carbonate 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (2R)-2-[(1R)-1,2-dihydroxyethyl]-4-octadecoxy-3-phenylmethoxy-2H-furan-5-one
  参考文献：
  名称：

  Studies on scavengers of active oxygen species. 1. Synthesis and biological activity of 2-O-alkylascorbic acids

  摘要：

  A novel series of 2-O-alkylascorbic acids (5a-u) was synthesized, and their scavenging activities against active oxygen species as well as their suppressive effects on the arrhythmias in rat heart ischemia-reperfusion models were evaluated. Some 2-O-alkylascorbic acids (5e-1) exhibited potent inhibiting activities against lipid peroxidation in rat brain homogenates and in alleviating effects in the ischemia-reperfusion models. Studies on the structure-activity relationship demonstrated that a free 3-enolic hydroxyl group and the longer alkyl chains substituted on the 2-hydroxyl group of ascorbic acid were beneficial for the biological and pharmacological activities. 2-O-Octadecylascorbic acid (5k, CV-3611), one of the most potent and promising compounds, markedly inhibited lipid peroxidation (IC50 = 4.3 X 10(-6) M) and alleviated myocardial lesions induced by ischemia-reperfusion at an oral dose of 1 mg/kg in rats.

  DOI：

  10.1021/jm00399a019

文献信息

• KATO, KANEYOSHI;TERAO, SHINJI;SHIMAMOTO, NORIO;HIRATA, MINORU, J. MED. CHEM., 31,(1988) N 4, 793-798
  作者：KATO, KANEYOSHI、TERAO, SHINJI、SHIMAMOTO, NORIO、HIRATA, MINORU

  DOI：——

  日期：——
• Pharmaceutical compositions containing ascorbic acid derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0202589B1

  公开（公告）日：1990-02-28
• US4959362A
  申请人：——

  公开号：US4959362A

  公开（公告）日：1990-09-25
• Studies on scavengers of active oxygen species. 1. Synthesis and biological activity of 2-O-alkylascorbic acids
  作者：Kaneyoshi Kato、Shinji Terao、Norio Shimamoto、Minoru Hirata

  DOI：10.1021/jm00399a019

  日期：1988.4

  A novel series of 2-O-alkylascorbic acids (5a-u) was synthesized, and their scavenging activities against active oxygen species as well as their suppressive effects on the arrhythmias in rat heart ischemia-reperfusion models were evaluated. Some 2-O-alkylascorbic acids (5e-1) exhibited potent inhibiting activities against lipid peroxidation in rat brain homogenates and in alleviating effects in the ischemia-reperfusion models. Studies on the structure-activity relationship demonstrated that a free 3-enolic hydroxyl group and the longer alkyl chains substituted on the 2-hydroxyl group of ascorbic acid were beneficial for the biological and pharmacological activities. 2-O-Octadecylascorbic acid (5k, CV-3611), one of the most potent and promising compounds, markedly inhibited lipid peroxidation (IC50 = 4.3 X 10(-6) M) and alleviated myocardial lesions induced by ischemia-reperfusion at an oral dose of 1 mg/kg in rats.