3-Thioxo-3H-1,2-dithiol-4-carbonsaeure-methylester | 133082-59-4

• 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: 3-Thioxo-3H-1,2-dithiol-4-carbonsaeure-methylester
• 英文别名: methyl 3-thioxo-3H-1,2-dithiole-4-carboxylate；Methyl 3-sulfanylidenedithiole-4-carboxylate
• CAS: 133082-59-4
• 化学式: C₅H₄O₂S₃
• 分子量: 192.284
• InChiKey: DEEICCWUIHVZOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Thioxo-3H-1,2-dithiol-4-carbonsaeure-methylester 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 8.0h， 以65%的产率得到3-thioxo-3H-1,2-dithiole-4-carboxylic acid
  参考文献：
  名称：

  Über die Farbreaktion nachOgston On Ogston's Colour Test

  摘要：

  DOI：

  10.1002/ardp.19913240214
• 作为产物：
  描述：

  diethyl 2-(ethoxymethylene)malonate 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 tetraphosphorus decasulfide 、 六甲基二硅氧烷 、 水 、 溶剂黄146 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 0.5h， 生成 3-Thioxo-3H-1,2-dithiol-4-carbonsaeure-methylester
  参考文献：
  名称：

  Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

  摘要：

  Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine- or H2O2 -induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.

  DOI：

  10.1021/acs.jafc.9b06360

文献信息

• Schachtner; Nienaber; Stachel, Pharmazie, 1999, vol. 54, # 5, p. 335 - 340
  作者：Schachtner、Nienaber、Stachel、Waisser

  DOI：——

  日期：——
• STACHEL, HANS-DIETRICH;ZOUKAS, THOMAS, ARCH. PHARM., 324,(1991) N, C. 131-132
  作者：STACHEL, HANS-DIETRICH、ZOUKAS, THOMAS

  DOI：——

  日期：——
• Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes
  作者：Zi-Long Song、Feifei Bai、Baoxin Zhang、Jianguo Fang

  DOI：10.1021/acs.jafc.9b06360

  日期：2020.2.19

  Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine- or H2O2 -induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.
• Über die Farbreaktion nachOgston On Ogston's Colour Test
  作者：Hans-Dietrich Stachel、Thomas Zoukas

  DOI：10.1002/ardp.19913240214

  日期：——