5-(2-chlorophenyl)-3H-1,2-dithiole-3-thione | 42766-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(2-chlorophenyl)-3H-1,2-dithiole-3-thione
• 英文别名: 5-(2-Chlorophenyl)dithiole-3-thione
• CAS: 42766-13-2
• 化学式: C₉H₅ClS₃
• 分子量: 244.79
• InChiKey: UHGYPXISCQTQOG-UHFFFAOYSA-N

物化性质

• 熔点：
  129 °C(Solv: ethanol (64-17-5))
• 沸点：
  397.1±52.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(2-chlorophenyl)-3H-1,2-dithiole-3-thione 在 mercury(II) diacetate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 5-(2-chlorophenyl)-3H-1,2-dithiole-3-one
  参考文献：
  名称：

  在大鼠肝微粒体存在下作为硫化氢供体的各种芳基二硫酮和芳基二硫酮的比较。

  摘要：

  据报道，ADT (5-(p-甲氧基苯基)-3H-1,2-dithiole-3-thione, anetholedithiolethion, Sulfarlem) 和 ADO (5-(p-甲氧基苯基)-3H-1,2) 的微粒体代谢-dithiole-3-one, anetholedithiolone) 导致 H2S 的形成，主要来源于由细胞色素 P450 依赖性单加氧酶催化的氧化作用，并且在这些条件下，ADO 是比 ADT 更好的 H2S 供体。本文比较了 18 种二硫硫酮和 ADT 和 ADO 的二硫醇酮类似物与大鼠肝微粒体孵育后的 H2S 供体能力。它表明，对于所有研究的化合物，在与微粒体和 NADPH 孵育后获得了最大的 H2S 形成，并且这种形成在 N-苄基咪唑（一种已知的细胞色素 P450 抑制剂）存在下大大减少。这表明所有研究的化合物形成 H2S 需要，正如之前在 ADT 和 ADO

  DOI：

  10.1124/dmd.119.090274
• 作为产物：
  描述：

  (2-氯苯甲酰)乙酸乙酯 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-(2-chlorophenyl)-3H-1,2-dithiole-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

• Switching Selectivity of α-Enolic Dithioesters: One Pot Access to Functionalized 1,2- and 1,3-Dithioles
  作者：Suvajit Koley、Tanmoy Chanda、Subhasis Samai、Maya Shankar Singh

  DOI：10.1021/acs.joc.6b01802

  日期：2016.12.2

  An operationally simple cascade protocol has been developed for the construction of 1,2- and 1,3-dithiole derivatives from alpha-enolic dithio esters. 1,2-Dithioles are achieved by the reaction of dithioesters with elemental sulfur in the presence of InCl3 under solvent-free conditions. 1,3-Dithioles have been constructed via DABCO mediated self coupling of dithioesters in open air enabling the formation of two new C-S bonds and one ring in a single operation in contiguous fashion. The reactions proceeded smoothly affording the desired sulfur-rich heterocycles in good to excellent yields, exhibiting gram-scale ability and broad functional group tolerance utilizing easy to handle cheap and easily available reagents. The probable mechanisms for the formation of suggested. 1,2- and 1,3-dithioles from alpha-enolic dithioesters have been suggested.
• Synthesis and in vitro anti-HIV evaluation of disulfide linked derivatives of 1,2-dithiol-3-ylidene ketones containing a 2,3-dichloro-4-phenoxy acetic acid moiety
  作者：A Nuhrich、M Varache-Lembège、C Jarry、G Devaux

  DOI：10.1016/0223-5234(92)90122-h

  日期：1992.11
• MISRA P. K.; MISRA S. C.; MOHAPATRA R. M.; MITTRA A. S., J. INDIAN CHEM., SOC., 1979, 56, NO 4, 404-407
  作者：MISRA P. K.、 MISRA S. C.、 MOHAPATRA R. M.、 MITTRA A. S.

  DOI：——

  日期：——