2,3-di(3-propynylthio)quinoline | 1557967-59-5

• 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
• 英文名称: 2,3-di(3-propynylthio)quinoline
• 英文别名: Dipropargylthioquinoline；2,3-bis(prop-2-ynylsulfanyl)quinoline
• CAS: 1557967-59-5
• 化学式: C₁₅H₁₁NS₂
• 分子量: 269.391
• InChiKey: LOCBBUZZPOFNOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  63.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-chloroquinoline N-oxide 在 三氯氧磷 、 sodium thiomethoxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2,3-di(3-propynylthio)quinoline
  参考文献：
  名称：

  Synthesis, molecular docking study, and evaluation of the antiproliferative action of a new group of propargylthio- and propargylselenoquinolines

  摘要：

  This study describes the synthesis of a new group of halogenopropargylthio-, dipropargylthio-, and halogenopropargylseleno-quinoline derivatives. The ability of all of the synthesized compounds to inhibit the proliferation of the T-47D, MCF-7, MDA-MB-231, and SNB-19 cell lines was determined with the WST-1 assay. The normal fibroblast cell line (HFF-1) was used as a control. The cytotoxic properties of these new, modified propargylquinoline derivatives were comparable to those of cisplatin. The most active compounds, 4,7-dipropargylthiquinoline (8b) and 7-chloro-4-propargylselenoquinoline (5b), were docked into the binding site of human CYP1A1 and CYP1B1. Our data indicate that these derivatives may present promising chemotherapeutic agents, possibly targeting CYP1s pathway.

  DOI：

  10.1007/s00044-014-0922-3