(R)-2-(((4-chlorophenyl)thio)methyl)oxirane

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (R)-2-(((4-chlorophenyl)thio)methyl)oxirane
• 英文别名: (2R)-2-[(4-chlorophenyl)sulfanylmethyl]oxirane
• 化学式: C₉H₉ClOS
• 分子量: 200.689
• InChiKey: GOLBZWJZSUDMKP-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12.53
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R)-2-(((4-chlorophenyl)thio)methyl)oxirane 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 copper(l) iodide 、 magnesium sulfate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.17h， 生成 (6R)-6-(((4-chlorophenyl)sulfinyl)methyl)-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  A low toxic CRM1 degrader: Synthesis and anti-proliferation on MGC803 and HGC27

  摘要：

  Chromosome region maintenance 1 (CRM1) is the sole nuclear exporter of several tumor suppressor, a growth regulatory protein as an attractive cancer drug target. In the present work, a novel CRM1 degrader was discovered from newly synthesized alpha, beta-unsaturated-delta-lactone based on a natural product Goniothalamin. It induces apoptosis of both MGC803 and HGC27 cell lines via degrading CRM1. Selective inhibition was observed for the proliferation of gastric cancer cell lines MGC803, HGC27 comparing to Human Gastric Mucosal Epithelial Cell Line (GES1). For the first time, CRM1 inhibitor or degrader inducing apoptosis in gastric carcinoma was investigated. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112708
• 作为产物：
  描述：

  右旋环氧氯丙烷 、 4-氯苯硫酚 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 水 为溶剂， 反应 0.5h， 以37.83%的产率得到(R)-2-(((4-chlorophenyl)thio)methyl)oxirane
  参考文献：
  名称：

  A low toxic CRM1 degrader: Synthesis and anti-proliferation on MGC803 and HGC27

  摘要：

  Chromosome region maintenance 1 (CRM1) is the sole nuclear exporter of several tumor suppressor, a growth regulatory protein as an attractive cancer drug target. In the present work, a novel CRM1 degrader was discovered from newly synthesized alpha, beta-unsaturated-delta-lactone based on a natural product Goniothalamin. It induces apoptosis of both MGC803 and HGC27 cell lines via degrading CRM1. Selective inhibition was observed for the proliferation of gastric cancer cell lines MGC803, HGC27 comparing to Human Gastric Mucosal Epithelial Cell Line (GES1). For the first time, CRM1 inhibitor or degrader inducing apoptosis in gastric carcinoma was investigated. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112708

文献信息

• A low toxic CRM1 degrader: Synthesis and anti-proliferation on MGC803 and HGC27
  作者：Hai-Wei Xu、Shilong Jia、Mengbo Liu、Xiaobo Li、Xia Meng、Xinxin Wu、Lu Yu、Menglin Wang、Cheng-Yun Jin

  DOI：10.1016/j.ejmech.2020.112708

  日期：2020.11

  Chromosome region maintenance 1 (CRM1) is the sole nuclear exporter of several tumor suppressor, a growth regulatory protein as an attractive cancer drug target. In the present work, a novel CRM1 degrader was discovered from newly synthesized alpha, beta-unsaturated-delta-lactone based on a natural product Goniothalamin. It induces apoptosis of both MGC803 and HGC27 cell lines via degrading CRM1. Selective inhibition was observed for the proliferation of gastric cancer cell lines MGC803, HGC27 comparing to Human Gastric Mucosal Epithelial Cell Line (GES1). For the first time, CRM1 inhibitor or degrader inducing apoptosis in gastric carcinoma was investigated. (C) 2020 Elsevier Masson SAS. All rights reserved.