2-((3,4,4-trifluorobut-3-en-1-yl)thio)pyridine | 27443-10-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-((3,4,4-trifluorobut-3-en-1-yl)thio)pyridine
• 英文别名: 2-(3,4,4-Trifluor-3-butenylthio)-pyridin；2-(3,4,4-Trifluorobut-3-enylsulfanyl)pyridine；2-(3,4,4-trifluorobut-3-enylsulfanyl)pyridine
• CAS: 27443-10-3
• 化学式: C₉H₈F₃NS
• 分子量: 219.23
• InChiKey: VYRXHFKYMDOAIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((3,4,4-trifluorobut-3-en-1-yl)thio)pyridine 在 双氧水 、 溶剂黄146 作用下， 以 水 为溶剂， 以51.3%的产率得到2-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)pyridine
  参考文献：
  名称：

  Fluoroalkane thioheterocyclic derivatives and their antitumor activity

  摘要：

  Two series of novel trifluorobutenyl derivatives of heterocyclic with convenient and efficient synthesis methods and their antitumor activity on three cell lines have been reported for the first time. The derivatives were synthesized by the nucleophilic substitution between 4-bromo-1,1,2-trifluorobutene-1-ene and commercially available nitrogen-containing heterocycles with sulfydryl or monosubstituted malononitrile. The twenty-four new compounds were characterized by (HNMR)-H-1, (CNMR)-C-13 and HR-MS. Totally, thirty-seven compounds were evaluated for the antitumor activity on three cancer cell lines (SH-SY5Y, MCF-7 and HepG2) using conventional MIT assay. The pharmacological results indicated that the compounds 3c, 3h, 4c, 8, 9, 10 and 11 showed potent to moderate antitumor activity against three cancer cell lines, with IC50 values ranging between 0.4 mu M and 41.5 mu M. Even though they had less active than the reference compound taxol against MCF-7 and HepG2 lines, but they were better than the reference compound noscapine against SH-SY5Y cells, especially the compound 3h with a IC50 value of 0.4 mu M. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.031
• 作为产物：
  描述：

  2-巯基吡啶 、 4-溴-1,1,2-三氟-1-丁烯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以68%的产率得到2-((3,4,4-trifluorobut-3-en-1-yl)thio)pyridine
  参考文献：
  名称：

  Fluoroalkane thioheterocyclic derivatives and their antitumor activity

  摘要：

  Two series of novel trifluorobutenyl derivatives of heterocyclic with convenient and efficient synthesis methods and their antitumor activity on three cell lines have been reported for the first time. The derivatives were synthesized by the nucleophilic substitution between 4-bromo-1,1,2-trifluorobutene-1-ene and commercially available nitrogen-containing heterocycles with sulfydryl or monosubstituted malononitrile. The twenty-four new compounds were characterized by (HNMR)-H-1, (CNMR)-C-13 and HR-MS. Totally, thirty-seven compounds were evaluated for the antitumor activity on three cancer cell lines (SH-SY5Y, MCF-7 and HepG2) using conventional MIT assay. The pharmacological results indicated that the compounds 3c, 3h, 4c, 8, 9, 10 and 11 showed potent to moderate antitumor activity against three cancer cell lines, with IC50 values ranging between 0.4 mu M and 41.5 mu M. Even though they had less active than the reference compound taxol against MCF-7 and HepG2 lines, but they were better than the reference compound noscapine against SH-SY5Y cells, especially the compound 3h with a IC50 value of 0.4 mu M. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.031