4-(4-hydroxy-2-butynylthio)-3-(methylthio)quinoline | 1076231-27-0

• 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: 4-(4-hydroxy-2-butynylthio)-3-(methylthio)quinoline
• 英文别名: 4-(4-Hydroxy-2-butynylthio)-3-methylthioquinoline；4-(3-methylsulfanylquinolin-4-yl)sulfanylbut-2-yn-1-ol
• CAS: 1076231-27-0
• 化学式: C₁₄H₁₃NOS₂
• 分子量: 275.395
• InChiKey: SMPGYOXMLPIUCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  83.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-hydroxy-2-butynylthio)-3-(methylthio)quinoline 、 氯甲酸乙酯 在 吡啶 作用下， 以 苯 为溶剂， 反应 1.0h， 以93%的产率得到4-(4-ethoxycarbonyloxy-2-butynylthio)-3-(methylthio)quinoline
  参考文献：
  名称：

  Synthesis and in vitro antiproliferative activity of novel (4-chloro- and 4-acyloxy-2-butynyl)thioquinolines

  摘要：

  The series of new acetylenic thioquinolines containing propargyl, 4-chloro-2-butynyl, and 4-acyloxy-2-butynyl groups have been prepared and tested for antiproliferative activity in vitro against human [SW707 (colorectal adenocarcinoma), CCRF/CEM (leukemia), T47D (breast cancer)] and murine [P388 (leukemia), B16 (melanoma)] cancer lines. Most of the obtained compounds exhibited antiproliferative activity, especially compounds 8, 12, and 21 showed the ID50 values ranging from 0.4 to 3.8 mu g/ml comparable to that of cisplatin used as reference compounds.

  DOI：

  10.1007/s00044-010-9495-y
• 作为产物：
  描述：

  4-bromobut-2-yn-1-ol 、 4-chloro-3-methylsulfanylquinoline 在 硫脲 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.25h， 以53%的产率得到4-(4-hydroxy-2-butynylthio)-3-(methylthio)quinoline
  参考文献：
  名称：

  Synthesis and antiproliferative activity in vitro of novel (2-butynyl)thioquinolines

  摘要：

  The series of new acetylenic thioquinolines containing propargyl, 2-butynyl, 4-bromo-2-butynyl, and 4-hydroxy- 2-butynyl groups has been prepared and tested for antiproliferative activity in vitro against human [SW707 ( colorectal adenocarcinoma), CCRF/CEM ( leukemia)] and murine [P388 ( leukemia), B16 ( melanoma)] cancer lines. All the compounds obtained exhibited antiproliferative activity. The most active compounds 7, 16, 17, and 19 have the ID(50) values ranging from 0.2 to 4.6 mu g/ml comparable to that of cisplatin used as referencecompounds. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.047

文献信息

• Synthesis and in vitro antiproliferative activity of novel (4-chloro- and 4-acyloxy-2-butynyl)thioquinolines
  作者：Stanisław Boryczka、Wojciech Mól、Magdalena Milczarek、Joanna Wietrzyk、Ewa Bębenek

  DOI：10.1007/s00044-010-9495-y

  日期：2011.11

  The series of new acetylenic thioquinolines containing propargyl, 4-chloro-2-butynyl, and 4-acyloxy-2-butynyl groups have been prepared and tested for antiproliferative activity in vitro against human [SW707 (colorectal adenocarcinoma), CCRF/CEM (leukemia), T47D (breast cancer)] and murine [P388 (leukemia), B16 (melanoma)] cancer lines. Most of the obtained compounds exhibited antiproliferative activity, especially compounds 8, 12, and 21 showed the ID50 values ranging from 0.4 to 3.8 mu g/ml comparable to that of cisplatin used as reference compounds.
• Synthesis and antiproliferative activity in vitro of novel (2-butynyl)thioquinolines
  作者：W. Mól、M. Matyja、B. Filip、J. Wietrzyk、S. Boryczka

  DOI：10.1016/j.bmc.2008.07.047

  日期：2008.9

  The series of new acetylenic thioquinolines containing propargyl, 2-butynyl, 4-bromo-2-butynyl, and 4-hydroxy- 2-butynyl groups has been prepared and tested for antiproliferative activity in vitro against human [SW707 ( colorectal adenocarcinoma), CCRF/CEM ( leukemia)] and murine [P388 ( leukemia), B16 ( melanoma)] cancer lines. All the compounds obtained exhibited antiproliferative activity. The most active compounds 7, 16, 17, and 19 have the ID(50) values ranging from 0.2 to 4.6 mu g/ml comparable to that of cisplatin used as referencecompounds. (C) 2008 Elsevier Ltd. All rights reserved.