7-chloro-4-(3-propynylthio)quinoline | 1557967-22-2

• 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: 7-chloro-4-(3-propynylthio)quinoline
• 英文别名: 7-chloro-4-propargylthioquinoline；7-Chloro-4-propargylthioquinoline；7-chloro-4-prop-2-ynylsulfanylquinoline
• CAS: 1557967-22-2
• 化学式: C₁₂H₈ClNS
• 分子量: 233.721
• InChiKey: MZSQQHCHWAFKDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-溴丙酸 、 7-chloro-4-(3-propynylthio)quinoline 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 碳酸氢钠 、 维生素 C 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以71%的产率得到3-{4-[methylthio-(7-chloro-4-quinolyl)]-1H-1,2,3-triazol-1-yl}propanoic acidb
  参考文献：
  名称：

  Synthesis and anticancer activity evaluation of a quinoline-based 1,2,3-triazoles

  摘要：

  A small library of methylthio- or methylseleno-quinolyl-linked 1,4-disubstituted 1,2,3-triazole conjugates has been synthesized from the halogenopropargylthio- or halogenopropargylseleno-quinolines through one-pot click reaction. The ability of all of the synthesized compounds to inhibit the proliferation of the C-32, T-47D, and SNB-19 cell lines was determined using the WST-1 assay. The cytotoxic properties of these new, modified derivatives of quinolyl-triazoles were comparable to those of cisplatin. Two of them, 1-benzyl-4-[methylseleno-(6-chloro-4-quinolyl)]-1H-1,2,3-triazole (2e) and 1-benzyl-4-[methylseleno-(8-bromo-4-quinolyl)]-1H-1,2,3-triazole (2j) demonstrated significant activity on the C-32 and SNB-19 cell lines.

  DOI：

  10.1007/s00044-017-1943-5
• 作为产物：
  描述：

  4,7-二氯喹啉 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.25h， 生成 7-chloro-4-(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

文献信息

• Synthesis, molecular docking study, and evaluation of the antiproliferative action of a new group of propargylthio- and propargylselenoquinolines
  作者：Krzysztof Marciniec、Małgorzata Latocha、Stanisław Boryczka、Rafał Kurczab

  DOI：10.1007/s00044-014-0922-3

  日期：2014.7

  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.
• Synthesis and anticancer activity evaluation of a quinoline-based 1,2,3-triazoles
  作者：Krzysztof Marciniec、Małgorzata Latocha、Rafał Kurczab、Stanisław Boryczka

  DOI：10.1007/s00044-017-1943-5

  日期：2017.10

  A small library of methylthio- or methylseleno-quinolyl-linked 1,4-disubstituted 1,2,3-triazole conjugates has been synthesized from the halogenopropargylthio- or halogenopropargylseleno-quinolines through one-pot click reaction. The ability of all of the synthesized compounds to inhibit the proliferation of the C-32, T-47D, and SNB-19 cell lines was determined using the WST-1 assay. The cytotoxic properties of these new, modified derivatives of quinolyl-triazoles were comparable to those of cisplatin. Two of them, 1-benzyl-4-[methylseleno-(6-chloro-4-quinolyl)]-1H-1,2,3-triazole (2e) and 1-benzyl-4-[methylseleno-(8-bromo-4-quinolyl)]-1H-1,2,3-triazole (2j) demonstrated significant activity on the C-32 and SNB-19 cell lines.