2-chloroethenesulfonyl chloride | 1071562-91-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 磺酰卤
• 英文名称: 2-chloroethenesulfonyl chloride
• 英文别名: (E)-2-chloroethene-1-sulfonyl chloride；(E)-2-chloroethenesulfonyl chloride
• CAS: 1071562-91-8
• 化学式: C₂H₂Cl₂O₂S
• 分子量: 161.009
• InChiKey: HDRWVCCMIQAASS-OWOJBTEDSA-N

物化性质

• 熔点：
  211-212 °C
• 沸点：
  206.1±32.0 °C(Predicted)
• 密度：
  1.626±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲醇 、 2-chloroethenesulfonyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到甲基乙烯磺酸酯
  参考文献：
  名称：

  A Novel Potent Nicotinamide Phosphoribosyltransferase Inhibitor Synthesized via Click Chemistry

  摘要：

  The inhibition of NAD synthesis or salvage pathways has been proposed as a novel target for antitumoral drugs. Two molecules with this mechanism of action are at present undergoing clinical trials. In searching for similar novel molecules, we exploited copper-catalyzed [3 + 2] cycloaddition between azides and alkynes (click chemistry) to synthesize 185 novel analogues. The most promising compound displays an IC50 for cytotoxicity in vitro of 3.8 +/- 0.3 nM and an IC50 for NAD depletion of 3.0 +/- 0.4 nM. Herein, we strengthen previous data suggesting that this class of compounds induces autophagic cell death. In addition to characterizing this compound and providing a rationale via molecular docking, we reinforce the excellent potential of click chemistry for rapidly generating structure-activity relationships and for drug screening.

  DOI：

  10.1021/jm9010669

文献信息

• A Novel Potent Nicotinamide Phosphoribosyltransferase Inhibitor Synthesized via Click Chemistry
  作者：Giampiero Colombano、Cristina Travelli、Ubaldina Galli、Antonio Caldarelli、Maria Giovanna Chini、Pier Luigi Canonico、Giovanni Sorba、Giuseppe Bifulco、Gian Cesare Tron、Armando A. Genazzani

  DOI：10.1021/jm9010669

  日期：2010.1.28

  The inhibition of NAD synthesis or salvage pathways has been proposed as a novel target for antitumoral drugs. Two molecules with this mechanism of action are at present undergoing clinical trials. In searching for similar novel molecules, we exploited copper-catalyzed [3 + 2] cycloaddition between azides and alkynes (click chemistry) to synthesize 185 novel analogues. The most promising compound displays an IC50 for cytotoxicity in vitro of 3.8 +/- 0.3 nM and an IC50 for NAD depletion of 3.0 +/- 0.4 nM. Herein, we strengthen previous data suggesting that this class of compounds induces autophagic cell death. In addition to characterizing this compound and providing a rationale via molecular docking, we reinforce the excellent potential of click chemistry for rapidly generating structure-activity relationships and for drug screening.