6-氯-9-巯基-2-甲氧基-吖啶 | 2411-88-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 6-氯-9-巯基-2-甲氧基-吖啶
• 英文名称: 6-chloro-2-methoxy-9-thioacridine
• 英文别名: 6-chloro-2-methoxy-9-thioacridone；qiunacrine；6-chloro-2-methoxy-10H-acridine-9-thione；6-Chlor-2-methoxy-10H-acridin-9-thion；6-Chloro-2-methoxy-9-acridinethiol；6-chloro-2-methoxy-10H-acridine-9-thione
• CAS: 2411-88-3
• 化学式: C₁₄H₁₀ClNOS
• 分子量: 275.759
• InChiKey: IWJLVRYUVAGSGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-氯-9-巯基-2-甲氧基-吖啶 在 zinc diacetate 、 苯酚 作用下， 生成 米帕林
  参考文献：
  名称：

  Kitani, Nippon Kagaku Zasshi, 1954, vol. 75, p. 475,476

  摘要：

  DOI：
• 作为产物：
  描述：

  6-chloro-2-methoxyacridone 在 diphosphorus pentasulfide 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 2.5h， 以99%的产率得到6-氯-9-巯基-2-甲氧基-吖啶
  参考文献：
  名称：

  Thiations with Tetraphosphorus Decasulfide in Hexamethylphosphoric Triamide; Synthesis of Thioacronycine and Acridanethiones

  摘要：

  DOI：

  10.1055/s-1982-29851

文献信息

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Ag: MVol.B7, 1.20.2.6.5, page 58 - 63
  作者：

  DOI：——

  日期：——
• Inhibition of <i>Trypanosoma cruzi</i> Trypanothione Reductase by Acridines:  Kinetic Studies and Structure−Activity Relationships
  作者：Susanne Bonse、Christiane Santelli-Rouvier、Jacques Barbe、R. Luise Krauth-Siegel

  DOI：10.1021/jm990386s

  日期：1999.12.1

  Series of 9-amino and 9-thioacridines have been synthesized and studied as inhibitors of trypanothione reductase (TR) from Trypanosoma cruzi, the causative agent; of Chagas' disease. The compounds are structural analogues of the acridine drug mepacrine (quinacrine), which is a competitive inhibitor of the parasite enzyme, but not of human glutathione reductase, the closest related host enzyme. The 9-aminoacridines yielded apparent K-i values for competitive inhibition between 5 and 43 mu M. The most effective inhibitors were those with the methoxy and chlorine substituents of mepacrine and NH2 or NHCH(CH3)(CH2)(4)N(Et)(2) at C9. Detailed kinetic analyses revealed that in the case of 9-aminoacridines more than one inhibitor molecule can bind to the enzyme. In contrast, the 9-thioacridine derivatives inhibit TR with mixed-type kinetics. The kinetic data are discussed in light of the three-dimensional structure of the TR-mepacrine complex. The conclusion that structurally very similar acridine compounds can give rise to completely different inhibition patterns renders modelling studies and quantitative structure-activity relationships difficult.
• Synthesis and biological activity of acridinyl-9-thioacetic acids and their derivatives
  作者：A. N. Gaydukevich、G. P. Kazakov、A. A. Kravchenko、L. A. Porokhnyak、V. V. Pinchuk、D. L. Velikii

  DOI：10.1007/bf01145554

  日期：1987.9
• Bsiri; Johnson; Kayirere, Annales Pharmaceutiques Francaises, 1996, vol. 54, # 1, p. 27 - 33
  作者：Bsiri、Johnson、Kayirere、Galy、Galy、Barbe、Osuna、Mesa-Valle、Castilla Calvente、Rodriguez-Cabezas

  DOI：——

  日期：——
• Design, synthesis, docking study, α-glucosidase inhibition, and cytotoxic activities of acridine linked to thioacetamides as novel agents in treatment of type 2 diabetes
  作者：Maryam Mohammadi-Khanaposhtani、Sepideh Rezaei、Reza Khalifeh、Somaye Imanparast、Mohammad Ali Faramarzi、Saeed Bahadorikhalili、Malihe Safavi、Fatemeh Bandarian、Ensieh Nasli Esfahani、Mohammad Mahdavi、Bagher Larijani

  DOI：10.1016/j.bioorg.2018.06.035

  日期：2018.10

  A novel series of acridine linked to thioacetamides 9a-o were synthesized and evaluated for their alpha-glucosidase inhibitory and cytotoxic activities. All the synthesized compounds exhibited excellent alpha-glucosidase inhibitory activity in the range of IC50 = 80.0 +/- 2.0-383.1 +/- 2.0 mu M against yeast alpha-glucosidase, when compared to the standard drug acarbose (IC50 = 750.0 +/- 1.5 mu M). Among the synthesized compounds, 2-((6-chloro-2-methoxyacridin-9-yl)thio)-N-(p-tolyl) acetamide 9b displayed the highest alpha-glucosidase inhibitory activity (IC50 = 80.0 +/- 2.0 mu M). The in vitro cytotoxic assay of compounds 9a-o against MCF-7 cell line revealed that only the compounds 9d, 9c, and 9n exhibited cytotoxic activity. Cytotoxic compounds 9d, 9c, and 9n did not show cytotoxic activity against the normal human cell lines HDF. Kinetic study revealed that the most potent compound 9b is a competitive inhibitor with a K(i )of 85 mu M. Furthermore, the interaction modes of the most potent compounds 9b and 9f with alpha-glucosidase were evaluated through the molecular docking studies.