4-Nitro-6-trifluoromethyl-benzotrithiole 1-oxide | 75101-74-5

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 4-Nitro-6-trifluoromethyl-benzotrithiole 1-oxide
• 英文别名: 4-nitro-6-(trifluoromethyl)-1λ4,2,3-benzotrithiole 1-oxide
• CAS: 75101-74-5
• 化学式: C₇H₂F₃NO₃S₃
• 分子量: 301.291
• InChiKey: XSMGQWHAMIEVRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  S-[2-[[2-(dimethylcarbamoylsulfanyl)-3-nitro-5-(trifluoromethyl)phenyl]disulfanyl]-6-nitro-4-(trifluoromethyl)phenyl] N,N-dimethylcarbamothioate 在 过氧乙酸 、 sodium hydroxide 、 sodium hydrogensulfide 作用下， 以 二甲基亚砜 为溶剂， 生成 4-Nitro-6-trifluoromethyl-benzotrithiole 1-oxide
  参考文献：
  名称：

  Reactions of S,S'-[2,2'-dithiobis(nitrophenyl)] bis(N,N-dimethylcarbamothioates) with hydroxide and hydrosulfide anions. A synthesis of nitrobenzotrithioles

  摘要：

  DOI：

  10.1021/jo01311a063

文献信息

• Cytotoxic and cancer preventive activity of benzotrithioles and benzotrithiole oxides, synthetic analogues of varacins
  作者：Alexandra S. Kuzmich、Tatyana M. Khomenko、Sergey N. Fedorov、Tatyana N. Makarieva、Larisa K. Shubina、Nina I. Komarova、Dina V. Korchagina、Tatyana V. Rybalova、Konstantin P. Volcho、Nariman F. Salakhutdinov

  DOI：10.1007/s00044-016-1759-8

  日期：2017.2

  The cytotoxic and cancer preventive activities of synthetic analogs of natural varacins with polysulfide groups were studied. Presence of a sulfoxide group was found to have no significant effect on the cytotoxicity of these compounds. At the same time, this group is important for inhibition of colony formation of tumor cells treated with tumor promoter thus demonstrating cancer preventive activity. The most promising compound appears to be a synthetic varacin C analog, sulfoxide 10a, which exhibits the cancer preventive activity at dose into 100 times lower than its cytotoxic concentrations.
• RASHEED K.; WARKENTIN J. D., J. ORG. CHEM., 1980, 45, NO 23, 4806-4807
  作者：RASHEED K.、 WARKENTIN J. D.

  DOI：——

  日期：——
• Asymmetric oxidation of 4-nitro-6-trifluoromethyl-1,2,3-benzotrithiole
  作者：T. M. Khomenko、D. V. Korchagina、K. P. Volcho、N. F. Salakhutdinov

  DOI：10.1134/s1070428009090140

  日期：2009.9

  Both enantiomers of 4-nitro-6-trifluoromethyl-1,2,3-benzotrithiole 1-oxide as analogs of Varacins B and C were synthesized for the first time. The use of the Modena method ensures higher optical purity but lower yields of the chiral sulfoxides, as compared to the Kagan procedure.