4-methyl-5-phenyl-1,2-dithiole-3-thione | 10269-25-7

• 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: 4-methyl-5-phenyl-1,2-dithiole-3-thione
• 英文别名: 4-methyl-5-phenyl-3H-1,2-dithiole-3-thione；4-methyl-5-phenyl-1,2-dithiolene-3-thione；4-Methyl-5-phenyl-[1,2]dithiol-3-thion；4-methyl-5-phenyldithiole-3-thione
• CAS: 10269-25-7
• 化学式: C₁₀H₈S₃
• 分子量: 224.372
• InChiKey: AXJOQACGPIOTKY-UHFFFAOYSA-N

物化性质

• 熔点：
  103-104 °C
• 沸点：
  204-210 °C(Press: 1.5 Torr)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  4-methyl-5-phenyl-1,2-dithiole-3-thione 以61%的产率得到
  参考文献：
  名称：

  DROZD V. N.; UDACHIN YU. M.; BOGOMOLOVA G. S.; SERGEJCHUK V. V., ZH. ORGAN. XIMII, 1980, 16, NO 4, 883-886

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基-3-苯基丙烯酸 在 phosphorous (V) sulfide 、 sulfur 、 xylene 作用下， 生成 4-methyl-5-phenyl-1,2-dithiole-3-thione
  参考文献：
  名称：

  Jirousek; Starka, Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 1982,1984, 1985

  摘要：

  DOI：

文献信息

• Abrogation of Hyperosmotic Impairment of Insulin Signaling by a Novel Class of 1,2-Dithiole-3-thiones through the Inhibition of S6K1 Activation
  作者：Eun Ju Bae、Yoon Mee Yang、Sang Geon Kim

  DOI：10.1124/mol.107.044347

  日期：2008.5

  factor-alpha-induced hepatic insulin resistance via AMP-activated protein kinase-dependent p70S6 kinase (S6K) 1 inhibitory pathway. This study investigated whether oltipraz and a novel class of 1,2-dithiole-3-thiones were capable of preventing insulin resistance induced by hyperosmotic stress, thereby enhancing insulin-dependent signals, and, if so, whether the restoration of insulin signal was mediated

  来自该实验室的先前研究表明，吡喹硫酮和合成的二硫代硫酮通过AMP激活的蛋白激酶依赖性p70S6激酶（S6K）1抑制途径预防​​肿瘤坏死因子-α诱导的肝胰岛素抵抗。这项研究调查了oltipraz和一类新型的1,2-二硫代3-硫酮是否能够预防高渗应激诱导的胰岛素抵抗，从而增强胰岛素依赖性信号，如果可以，是否介导了胰岛素信号的恢复抑制高渗应激刺激的S6K1活性。在HepG2细胞中，oltipraz处理抑制了胰岛素受体底物（IRS）1丝氨酸磷酸化，这是山梨糖醇，甘露醇或氯化钠诱导的高渗应激诱导的胰岛素抵抗的标志。所以，这可以使细胞恢复胰岛素信号，这可以通过IRS1的丝氨酸与酪氨酸磷酸化比率的降低以及Akt和糖原合酶激酶（GSK）3beta磷酸化的增加来证明。高渗胁迫明显激活了S6K1；oltipraz预处理完全消除了S6K1激活。使用显性阴性S6K1的实验支持S6K1在高渗透压刺激的IRS1磷酸化
• Selective [3 + 2] Cycloaddition of Cyclopropenone Derivatives and Elemental Chalcogens
  作者：Jian Wu、Wen-Xia Gao、Xiao-Bo Huang、Yun-Bing Zhou、Miao-Chang Liu、Hua-Yue Wu

  DOI：10.1021/acs.orglett.0c01914

  日期：2020.7.17

  A highly efficient method is disclosed for the synthesis of 1,2-dichalcogen heterocycles via [3 + 2] cycloaddition of cyclopropenone derivatives and elemental chalcogens. Different from other cyclopropenone derivatives, cyclopropenselenones undergo unprecedented rearrangement with elemental sulfur. The features of this protocol include mild reaction conditions, high efficiency, excellent atom economy

  公开了一种通过环丙烯酮衍生物和元素硫属元素的[3 + 2]环加成合成1,2-二氢杂环的高效方法。与其他环丙烯酮衍生物不同，环丙烯酮与元素硫会经历前所未有的重排。该方案的特点包括反应条件温和，效率高，原子经济性好，克级能力和良好的区域选择性。
• Synthesis of 3H-1,2-dithiole-3-thiones by a novel oxidative cyclization
  作者：Thomas J. Curphey、H.Howard Joyner

  DOI：10.1016/s0040-4039(00)79295-1

  日期：1993.11

  Reaction of 3-oxo dithioic acids with a combination of hexamethyldisilathiane and N-chlorosuccinimide in the presence of a catalytic amount of imidazole brings about oxidative ring closure to 3H-1,2-dithiole-3-thiones. Yields vary from poor to good.
• 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.
• Woronkow; Broun; Karpenko, Zhurnal Obshchei Khimii, 1949, vol. 19, p. 1927,1939
  作者：Woronkow、Broun、Karpenko

  DOI：——

  日期：——