2-O-(4-bromobenzyl)-L-ascorbic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-O-(4-bromobenzyl)-L-ascorbic acid
• 英文别名: (2R)-4-[(4-bromophenyl)methoxy]-2-[(1S)-1,2-dihydroxyethyl]-3-hydroxy-2H-furan-5-one
• 化学式: C₁₃H₁₃BrO₆
• 分子量: 345.147
• InChiKey: RDDPAXQSQDHGLJ-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (R)-3-(4-Bromo-benzyloxy)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methoxymethoxy-5H-furan-2-one 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以53%的产率得到2-O-(4-bromobenzyl)-L-ascorbic 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

文献信息

• One-Pot 2-O-Alkylation of l-Ascorbic Acid
  作者：Shankar Thopate、Rohit Dengale、Mukund Kulkarni

  DOI：10.1055/s-0033-1338858

  日期：——

  One-pot 2-O-alkylation of L-ascorbic acid involving an in situ 3-O-silylation and desilylation sequence was investigated. Initially the 3-OH group was masked with a t-butyldimethylsilyl (TBDMS) group followed by alkylation of the 2-OH group. Removal of the TBDMS group using 20% sulfuric acid also resulted in hydrolysis of the 5,6-O-isopropylidene to give 2-O-alkyl derivatives of L-ascorbic acid. Selective removal of the 3-O-TBDMS with tetrabutylammonium fluoride (TBAF) gave 5,6-O-isopropylidene-2-O-alkyl derivatives of L-ascorbic acid in good overall yields. Through the application of this protocol, 5,6-O-isopropylidene 2-O-alkyl derivatives of L-ascorbic acid as well as 2-O-alkyl derivatives of L-ascorbic acid may be easily accessed.
• 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：——
• 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.