4-(3-hydroxypropane-1-thio)-2,6-bis(1,3-dioxolan-2-yl)pyridine | 656826-69-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(3-hydroxypropane-1-thio)-2,6-bis(1,3-dioxolan-2-yl)pyridine
• 英文别名: 3-[(2,6-Di-1,3-dioxolan-2-yl-4-pyridinyl)thio]-1-propanol；3-[2,6-bis(1,3-dioxolan-2-yl)pyridin-4-yl]sulfanylpropan-1-ol
• CAS: 656826-69-6
• 化学式: C₁₄H₁₉NO₅S
• 分子量: 313.375
• InChiKey: TWRPHPZUZAIORV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  95.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(3-hydroxypropane-1-thio)-2,6-bis(1,3-dioxolan-2-yl)pyridine 在 硫酸 、 氢溴酸 作用下， 以 水 为溶剂， 反应 3.0h， 以89%的产率得到4-(3-bromopropane-1-thio)-2,6-diformylpyridine
  参考文献：
  名称：

  Mitochondrially targeted antioxidants

  摘要：

  本发明提供了线粒体定向抗氧化化合物，包括一个脂溶性阳离子基团与一个抗氧化基团共价耦合，该抗氧化基团可以是超氧化物歧化酶（SOD）类似物或谷胱甘肽过氧化物酶（GPx）类似物。这些化合物可用于治疗需要减少氧化应激的患者。

  公开号：

  US20040029851A1
• 作为产物：
  描述：

  4-溴吡啶-2,6-二甲醇 在 sodium hydride 、 对甲苯磺酸 、 N-(2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-yl)acetamide tetrafluoroborate 作用下， 生成 4-(3-hydroxypropane-1-thio)-2,6-bis(1,3-dioxolan-2-yl)pyridine
  参考文献：
  名称：

  A Mitochondria-Targeted Macrocyclic Mn(II) Superoxide Dismutase Mimetic

  摘要：

  Superoxide (O-2(center dot-)) is the proximal mitochondrial reactive oxygen species underlying pathology and redox signaling. This central role prioritizes development of a mitochondria-targeted reagent selective for controlling O-2(center dot-). We have conjugated a mitochondria-targeting triphenylphosphonium (TPP) cation to a O-2(center dot-)-selective pentaaza macrocyclic Mn(II) superoxide dismutase (SOD) mimetic to make MitoSOD, a mitochondria-targeted SOD mimetic. MitoSOD showed rapid and extensive membrane potential-dependent uptake into mitochondria without loss of Mn and retained SOD activity. Pulse radiolysis measurements confirmed that MitoSOD was a very effective catalytic SOD mimetic. MitoSOD also catalyzes the ascorbate-dependent reduction of O-2(center dot-). The combination of mitochondrial uptake and O-2(center dot-) scavenging by MitoSOD decreased inactivation of the matrix enzyme aconitase caused by O-2(center dot-). MitoSOD is an effective mitochondria-targeted macrocyclic SOD mimetic that selectively protects mitochondria from O-2(center dot-) damage.

  DOI：

  10.1016/j.chembiol.2012.08.005

文献信息

• Mitochondrially targeted antioxidants
  申请人：Medical Research Council

  公开号：US20040029851A1

  公开（公告）日：2004-02-12

  The invention provides mitochondrially targeted antioxidant compounds comprising a lipophilic cation moiety covalently coupled to an antioxidant moiety which is either a superoxide dismutase (SOD) mimetic or a glutathione peroxidase mimetic. These compounds can be used to treat patients who would benefit from the reduction of oxidative stress.

  本发明提供了线粒体定向抗氧化化合物，包括一个脂溶性阳离子基团与一个抗氧化基团共价耦合，该抗氧化基团可以是超氧化物歧化酶（SOD）类似物或谷胱甘肽过氧化物酶（GPx）类似物。这些化合物可用于治疗需要减少氧化应激的患者。
• US6984636B2
  申请人：——

  公开号：US6984636B2

  公开（公告）日：2006-01-10
• A Mitochondria-Targeted Macrocyclic Mn(II) Superoxide Dismutase Mimetic
  作者：Geoffrey F. Kelso、Andrej Maroz、Helena M. Cochemé、Angela Logan、Tracy A. Prime、Alexander V. Peskin、Christine C. Winterbourn、Andrew M. James、Meredith F. Ross、Sally Brooker、Carolyn M. Porteous、Robert F. Anderson、Michael P. Murphy、Robin A.J. Smith

  DOI：10.1016/j.chembiol.2012.08.005

  日期：2012.10

  Superoxide (O-2(center dot-)) is the proximal mitochondrial reactive oxygen species underlying pathology and redox signaling. This central role prioritizes development of a mitochondria-targeted reagent selective for controlling O-2(center dot-). We have conjugated a mitochondria-targeting triphenylphosphonium (TPP) cation to a O-2(center dot-)-selective pentaaza macrocyclic Mn(II) superoxide dismutase (SOD) mimetic to make MitoSOD, a mitochondria-targeted SOD mimetic. MitoSOD showed rapid and extensive membrane potential-dependent uptake into mitochondria without loss of Mn and retained SOD activity. Pulse radiolysis measurements confirmed that MitoSOD was a very effective catalytic SOD mimetic. MitoSOD also catalyzes the ascorbate-dependent reduction of O-2(center dot-). The combination of mitochondrial uptake and O-2(center dot-) scavenging by MitoSOD decreased inactivation of the matrix enzyme aconitase caused by O-2(center dot-). MitoSOD is an effective mitochondria-targeted macrocyclic SOD mimetic that selectively protects mitochondria from O-2(center dot-) damage.