methyl 3,4,5,6-tetrahydro-3-thioxocyclopenta[c][1,2]dithiole-6-carboxylate | 1229452-60-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫醇
• 英文名称: methyl 3,4,5,6-tetrahydro-3-thioxocyclopenta[c][1,2]dithiole-6-carboxylate
• 英文别名: methyl 3-sulfanylidene-5,6-dihydro-4H-cyclopenta[c]dithiole-6-carboxylate
• CAS: 1229452-60-1
• 化学式: C₈H₈O₂S₃
• 分子量: 232.348
• InChiKey: CMDYQGNCNCPHGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二硫化碳 、 methyl 2-piperidin-1-ylcyclopent-2-ene-1-carboxylate 在 sulfur 作用下， 以 四氢呋喃 为溶剂， 生成 methyl 3,4,5,6-tetrahydro-3-thioxocyclopenta[c][1,2]dithiole-6-carboxylate
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Structure−Activity Relationships of Dithiolethiones as Inducers of Cytoprotective Phase 2 Enzymes

  摘要：

  Dithiolethiones are a family of promising cancer chemopreventive agents, and induction of phase 2 enzymes is key to their chemopreventive activities. Two dithiolethiones have been evaluated in humans for cancer prevention. While some chemopreventive activities were detected in several human studies, potential side effects are a concern. Herein, we report structure-activity relationships of 25 dithiolethiones. Several compounds show exceedingly potent and bladder specific activity in phase 2 enzyme induction. Structural features responsible for such activity, as well as those inhibiting the activity, are discussed. Moreover, the compounds activate and depend on Nrf2 for their inductive activities. Nrf2 is a major transcriptional stimulator of cytoprotective genes and is critical for cancer prevention. Thus, several new dithiolethiones that are highly promising for bladder cancer prevention have been identified. Because the compounds act specifically in the bladder, the likelihood of potential systemic toxicity may be low.

  DOI：

  10.1021/jm100425v

文献信息

• Synthesis, Biological Evaluation, and Structure−Activity Relationships of Dithiolethiones as Inducers of Cytoprotective Phase 2 Enzymes
  作者：Rex Munday、Yuesheng Zhang、Joseph D. Paonessa、Christine M. Munday、Alistair L. Wilkins、Jacob Babu

  DOI：10.1021/jm100425v

  日期：2010.6.24

  Dithiolethiones are a family of promising cancer chemopreventive agents, and induction of phase 2 enzymes is key to their chemopreventive activities. Two dithiolethiones have been evaluated in humans for cancer prevention. While some chemopreventive activities were detected in several human studies, potential side effects are a concern. Herein, we report structure-activity relationships of 25 dithiolethiones. Several compounds show exceedingly potent and bladder specific activity in phase 2 enzyme induction. Structural features responsible for such activity, as well as those inhibiting the activity, are discussed. Moreover, the compounds activate and depend on Nrf2 for their inductive activities. Nrf2 is a major transcriptional stimulator of cytoprotective genes and is critical for cancer prevention. Thus, several new dithiolethiones that are highly promising for bladder cancer prevention have been identified. Because the compounds act specifically in the bladder, the likelihood of potential systemic toxicity may be low.