(2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(methoxymethoxy)-4-octadecoxy-2H-furan-5-one | 107706-94-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(methoxymethoxy)-4-octadecoxy-2H-furan-5-one
• CAS: 107706-94-5
• 化学式: C₂₉H₅₂O₇
• 分子量: 512.728
• InChiKey: WHZPMQKGBUQYAY-LOSJGSFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.17
• 重原子数：
  36.0
• 可旋转键数：
  22.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(methoxymethoxy)-4-octadecoxy-2H-furan-5-one 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以84%的产率得到2-O-octadecylascorbic 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：

  5,6-O-isopropylidene-L-ascorbic 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 7.0h， 生成 (2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(methoxymethoxy)-4-octadecoxy-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

• Antiallergic Activity of 3-O-Dodecyl-l-ascorbic Acid
  作者：Takeru Koga、Naoaki Kawahara、Mei Aburada、Asako Ono、Shiori Mae、Aina Yoshida、Yuji Iwaoka、Hideyuki Ito、Akihiro Tai

  DOI：10.3390/molecules29010069

  日期：——

  synthesized, and their degranulation inhibitory activities were evaluated. Among ascorbic acid derivatives with butyl, octyl, dodecyl, hexadecyl, and octadecyl groups introduced at the C-2 or C-3 positions, an AA derivative with a dodecyl group introduced at the C-3 position, 3-O-dodecyl-l-ascorbic acid (compound 8), showed the strongest inhibitory activity against antigen-stimulated degranulation. Compound

  合成了2-O-烷基-L-抗坏血酸和3-O-烷基-L-抗坏血酸，并评价了它们的脱颗粒抑制活性。在C-2或C-3位引入丁基、辛基、十二烷基、十六烷基和十八烷基的抗坏血酸衍生物中，在C-3位引入十二烷基的AA衍生物为3-O-十二烷基-1 -抗坏血酸（化合物8），对抗原刺激的脱颗粒表现出最强的抑制活性。化合物8还抑制钙离子载体刺激的脱颗粒。将化合物8的C-6位的羟基替换为氨基的化合物11和将化合物8的C-3位的十二烷氧基替换为十二烷氨基的化合物12合成的，这些衍生物对抗原刺激的脱粒的抑制活性比化合物8弱。此外，口服化合物8抑制小鼠被动皮肤过敏反应，其效力与抗过敏剂奥沙米特相同。这些结果表明化合物8可能是抗过敏治疗的候选药物。
• 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：——