6-Brom-6-desoxy-3-O-methyl-L-ascorbinsaeure | 151163-46-1

• 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: 6-Brom-6-desoxy-3-O-methyl-L-ascorbinsaeure
• 英文别名: (2R)-2-[(1R)-2-bromo-1-hydroxyethyl]-4-hydroxy-3-methoxy-2H-furan-5-one
• CAS: 151163-46-1
• 化学式: C₇H₉BrO₅
• 分子量: 253.049
• InChiKey: LMPBSRGQTZANIG-WVZVXSGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-Brom-6-desoxy-3-O-methyl-L-ascorbinsaeure 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以90%的产率得到6-Iod-6-desoxy-3-O-methyl-L-ascorbinsaeure
  参考文献：
  名称：

  Goerlitzer; Baltrusch, Pharmazie, 2001, vol. 56, # 3, p. 208 - 213

  摘要：

  DOI：
• 作为产物：
  描述：

  Acetic acid (R)-2-bromo-1-((R)-4-hydroxy-3-methoxy-5-oxo-2,5-dihydro-furan-2-yl)-ethyl ester 在 盐酸 作用下， 以23%的产率得到6-Brom-6-desoxy-3-O-methyl-L-ascorbinsaeure
  参考文献：
  名称：

  Antioxidant and neutrophil-inhibiting properties of new 2-O-methyl-6-(alkylthio)ascorbic acid derivatives

  摘要：

  A series of new 6-(alkylthio)ascorbic acids was synthesized, and their inhibitory effects on lipid peroxidation and the oxidative burst of human neutrophils were tested. Of 12 structurally different lipophilic ascorbic acid derivatives 6-S-n-hexadecyl-2-O-methyl-6-deoxy-6-thio-L-ascorbic acid (7b; B-003) inhibited the Fe2+/ADP-induced lipid peroxidation of rat liver microsomes with an IC50 value of 2 mu M. In human neutrophils, 7b most potently inhibited the fMLP-induced oxidative burst in a cell density-dependent manner with an IC50 value Of 0.6 mu M at 5 x 10(5) cells/mL. Shorter alkyl chain lengths decreased the inhibitory potency for both lipid peroxidation and oxidative burst, but in general no correlation was found between the two parameters. Likewise, 6-S-n-hexadecyl-3-O-methyl-6-thio-L-ascorbic acid (7c; B-015), the regioisomer of 7b, was a potent antioxidant but did not affect the oxidative burst. Since superoxide anions generated by xanthine/ xanthine oxidase were not quenched by 7b, it became evident that its target was somewhere between receptor stimulation and NADPH-oxidase activation. By measuring the cellular concentrations of 7b and 7c, an accumulation of the first was found explaining its potency and the dependence on cell density. Expecting a pK(a) value of 3.3 for 7b and 7.7 for 7c a protonophore action of 7b was likely and could be verified by the drop in intracellular pH (pH(i)) which did not occur with 7b. Ionophores such as nigericin, CCCP, or propionic acid also lowered the pH(i) but did not inhibit the oxidative burst, indicating that the pH(i) drop was not the cause for this inhibition. 7b also strongly inhibited the fMLP-induced secretion of azurophilic (IC50 = 7 mu M) and specific (IC50 = 2.5 mu M) granules.

  DOI：

  10.1021/jm00077a005

文献信息

• Goerlitzer; Baltrusch, Pharmazie, 2001, vol. 56, # 3, p. 208 - 213
  作者：Goerlitzer、Baltrusch

  DOI：——

  日期：——
• Antioxidant and neutrophil-inhibiting properties of new 2-O-methyl-6-(alkylthio)ascorbic acid derivatives
  作者：Elmar Schmid、Volker Figala、Dagmar Roth、Volker Ullrich

  DOI：10.1021/jm00077a005

  日期：1993.12

  A series of new 6-(alkylthio)ascorbic acids was synthesized, and their inhibitory effects on lipid peroxidation and the oxidative burst of human neutrophils were tested. Of 12 structurally different lipophilic ascorbic acid derivatives 6-S-n-hexadecyl-2-O-methyl-6-deoxy-6-thio-L-ascorbic acid (7b; B-003) inhibited the Fe2+/ADP-induced lipid peroxidation of rat liver microsomes with an IC50 value of 2 mu M. In human neutrophils, 7b most potently inhibited the fMLP-induced oxidative burst in a cell density-dependent manner with an IC50 value Of 0.6 mu M at 5 x 10(5) cells/mL. Shorter alkyl chain lengths decreased the inhibitory potency for both lipid peroxidation and oxidative burst, but in general no correlation was found between the two parameters. Likewise, 6-S-n-hexadecyl-3-O-methyl-6-thio-L-ascorbic acid (7c; B-015), the regioisomer of 7b, was a potent antioxidant but did not affect the oxidative burst. Since superoxide anions generated by xanthine/ xanthine oxidase were not quenched by 7b, it became evident that its target was somewhere between receptor stimulation and NADPH-oxidase activation. By measuring the cellular concentrations of 7b and 7c, an accumulation of the first was found explaining its potency and the dependence on cell density. Expecting a pK(a) value of 3.3 for 7b and 7.7 for 7c a protonophore action of 7b was likely and could be verified by the drop in intracellular pH (pH(i)) which did not occur with 7b. Ionophores such as nigericin, CCCP, or propionic acid also lowered the pH(i) but did not inhibit the oxidative burst, indicating that the pH(i) drop was not the cause for this inhibition. 7b also strongly inhibited the fMLP-induced secretion of azurophilic (IC50 = 7 mu M) and specific (IC50 = 2.5 mu M) granules.