(5-(benzyloxy)-4-oxo-4H-pyran-2-yl)methyl methanesulfonate | 1064077-22-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (5-(benzyloxy)-4-oxo-4H-pyran-2-yl)methyl methanesulfonate
• 英文别名: methanesulfonic acid 5-benzyloxy-4-oxo-4H-pyran-2-ylmethyl ester；(4-oxo-5-phenylmethoxypyran-2-yl)methyl methanesulfonate
• CAS: 1064077-22-0
• 化学式: C₁₄H₁₄O₆S
• 分子量: 310.328
• InChiKey: QETPXXHOQLDCDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5-(benzyloxy)-4-oxo-4H-pyran-2-yl)methyl methanesulfonate 在 potassium carbonate 、 sodium bromide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 12.33h， 生成 5-(benzyloxy)-2-((4-(phenylsulfonyl)piperazin-1-yl)methyl)-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis of kojic acid-derived copper-chelating apoptosis inducing agents

  摘要：

  Three classes of kojic acid derivatives were synthesized and examined for their antiproliferative activity against HeLa cells. Both 8b and 11 co-treated with copper ion exhibited synergistic effect on the HeLa cell growth inhibition with GI(50) values of 11.9 and 7.1 mu M, respectively. Flow cytometric analysis of HeLa cells revealed that 11-Cu co-treatment induced the sub-G1 arrest in a dose-dependent manner, suggesting that the growth-inhibitory effect is attributed to DNA fragmentation. Moreover, western blot of HeLa cells cytosolic extracts displayed the cleavage of the 116-kDa protein poly(ADP-ribose) polymerase and activation of caspase-3 by the reduced level of the 32-kDa proenzyme, indicating that the caspase-dependent apoptotic pathway was involved. We further demonstrated that MAPK pathway regulators such as ERK and p38 were activated in response to 11-Cu co-treatment, suggesting that the intracellular oxidative stress was dramatically stimulated by the copper ion. Taken together, we have successfully synthesized kojic acid-derived copper-induced apoptotic agents.

  DOI：

  10.1007/s00044-012-0094-y
• 作为产物：
  描述：

  曲酸 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 (5-(benzyloxy)-4-oxo-4H-pyran-2-yl)methyl methanesulfonate
  参考文献：
  名称：

  Synthesis of kojic acid-derived copper-chelating apoptosis inducing agents

  摘要：

  Three classes of kojic acid derivatives were synthesized and examined for their antiproliferative activity against HeLa cells. Both 8b and 11 co-treated with copper ion exhibited synergistic effect on the HeLa cell growth inhibition with GI(50) values of 11.9 and 7.1 mu M, respectively. Flow cytometric analysis of HeLa cells revealed that 11-Cu co-treatment induced the sub-G1 arrest in a dose-dependent manner, suggesting that the growth-inhibitory effect is attributed to DNA fragmentation. Moreover, western blot of HeLa cells cytosolic extracts displayed the cleavage of the 116-kDa protein poly(ADP-ribose) polymerase and activation of caspase-3 by the reduced level of the 32-kDa proenzyme, indicating that the caspase-dependent apoptotic pathway was involved. We further demonstrated that MAPK pathway regulators such as ERK and p38 were activated in response to 11-Cu co-treatment, suggesting that the intracellular oxidative stress was dramatically stimulated by the copper ion. Taken together, we have successfully synthesized kojic acid-derived copper-induced apoptotic agents.

  DOI：

  10.1007/s00044-012-0094-y

文献信息

• Fluorinated derivatives of deferiprone
  申请人：Tam Tim Fat

  公开号：US20080242706A1

  公开（公告）日：2008-10-02

  The present invention relates to novel derivatives of deferiprone. In particular, the present invention relates to fluorinated derivatives of deferiprone or pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising same, processes for the manufacture thereof and their use in the treatment of neurodegenerative diseases caused by the presence of free iron or iron accumulation in neural tissues and in diseases wherein excess iron must be removed or redistributed.

  本发明涉及延胜肽的新颖衍生物。具体地，本发明涉及延胜肽的氟化衍生物或其药用盐，包括相同的药物组成部分，制造这些药物组成部分的方法以及它们在治疗由游离铁或神经组织中铁积累引起的神经退行性疾病以及需要去除或重新分配过量铁的疾病中的用途。
• Fluorinated Derivatives of Deferiprone
  申请人：Tam Tim Fat

  公开号：US20120095061A1

  公开（公告）日：2012-04-19

  The present invention relates to novel derivatives of deferiprone. In particular, the present invention relates to fluorinated derivatives of deferiprone or pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising same, processes for the manufacture thereof and their use in the treatment of neurodegenerative diseases caused by the presence of free iron or iron accumulation in neural tissues and in diseases wherein excess iron must be removed or redistributed.

  本发明涉及新型去铁酮衍生物。特别地，本发明涉及氟化去铁酮衍生物或其药学上可接受的盐、包含其的制药组合物、其制造过程以及在治疗由自由铁或神经组织中铁积累引起的神经退行性疾病和需要去除或重新分配过量铁的疾病中的应用。
• FLUORINATED DERIVATIVES OF DEFERIPRONE
  申请人：Apotex Technologies Inc.

  公开号：EP2134688B1

  公开（公告）日：2016-10-05
• US8026261B2
  申请人：——

  公开号：US8026261B2

  公开（公告）日：2011-09-27
• US8673943B2
  申请人：——

  公开号：US8673943B2

  公开（公告）日：2014-03-18