5-(3,4-methylenedioxyphenyl)-3H-1,2-dithiacyclopentene-3-thione | 14270-01-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(3,4-methylenedioxyphenyl)-3H-1,2-dithiacyclopentene-3-thione
• 英文别名: 5-(benzo[d][1,3]dioxol-5-yl)-3H-1,2-dithiole-3-thione；5-(3,4-Methylendihydroxyphenyl)-1,2-dithiol-3-thion；5-benzo[1,3]dioxol-5-yl-[1,2]dithiol-3-thione；5-Benzo[1,3]dioxol-5-yl-[1,2]dithiol-3-thion；5-(1,3-Benzodioxol-5-yl)dithiole-3-thione；5-(1,3-benzodioxol-5-yl)dithiole-3-thione
• CAS: 14270-01-0
• 化学式: C₁₀H₆O₂S₃
• 分子量: 254.354
• InChiKey: FJABXZHFZLCHAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(6-胡椒环基)-3-氧代丙酸乙酯 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 tetraphosphorus decasulfide 、 六甲基二硅氧烷 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 5-(3,4-methylenedioxyphenyl)-3H-1,2-dithiacyclopentene-3-thione
  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

• 3H-1,2-DITHIOCYCLOPENTENE-3-THIOKETONE COMPOUNDS AND APPLICATION THEREOF
  申请人：Soochow University

  公开号：EP2889294A1

  公开（公告）日：2015-07-01

  The present invention relates to the field of medicaments, and in particular relates to 3H-1,2-dithiocyclopentene-3-thione compounds and application thereof. 3H-1,2-dithiocyclopentene-3-thione compounds disclosed by the invention have new structures shown in formula I or formula II. Proved by experiments, 3H-1,2-dithiocyclopentene-3-thione compounds can directly protect neurons in a cellular model, and can significantly restrain excessive inflammatory responses of brain inflammatory cells; and by using 3H-1,2-dithiocyclopentene-3-thione, focal ischemic cerebral infarct volumes of mice can be remarkably reduced in an animal model. Therefore, the invention provides the application of 3H-1,2-dithiocyclopentene-3-thione compounds and pharmaceutically acceptable salts thereof in the preparation of medicaments for preventing or treating cerebral apoplexy diseases.

  本发明涉及药物领域，尤其涉及3H-1,2-二硫代环戊烯-3-硫酮化合物及其应用。本发明公开的 3H-1,2-二硫代环戊烯-3-硫酮化合物具有如式 I 或式 II 所示的新结构。通过实验证明，3H-1,2-二硫代环戊烯-3-硫酮化合物可以直接保护细胞模型中的神经元，并能显著抑制脑部炎症细胞的过度炎症反应；通过使用 3H-1,2-二硫代环戊烯-3-硫酮，可以显著降低动物模型中小鼠局灶性缺血性脑梗死的体积。因此，本发明提供了 3H-1,2-二硫代环戊烯-3-硫酮化合物及其药学上可接受的盐在制备预防或治疗脑中风疾病的药物中的应用。
• Lozac'h, Bulletin de la Societe Chimique de France, 1949, p. 840,844
  作者：Lozac'h

  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.