3-(cyclopropylcarbamoyl)benzenesulfonyl chloride | 1016501-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(cyclopropylcarbamoyl)benzenesulfonyl chloride
• 英文别名: 3-(Cyclopropylcarbamoyl)benzene-1-sulfonyl chloride
• CAS: 1016501-60-2
• 化学式: C₁₀H₁₀ClNO₃S
• mdl: MFCD09807507
• 分子量: 259.713
• InChiKey: SSINZHMPWHVPHC-UHFFFAOYSA-N

物化性质

• 沸点：
  438.6±28.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-chloro-3-(trifluoromethyl)phenyl)(4-(5-(4-hydroxyphenyl)-1H-imidazol-1-yl)piperidin-1-yl)methanone 、 3-(cyclopropylcarbamoyl)benzenesulfonyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以54.6%的产率得到4-(1-(1-(4-chloro-3-(trifluoromethyl)benzoyl)piperidin-4-yl)-1H-imidazol-5-yl)phenyl 3-(cyclopropylcarbamoyl)benzenesulfonate
  参考文献：
  名称：

  Potent Suppressive Effects of 1-Piperidinylimidazole Based Novel P2X7 Receptor Antagonists on Cancer Cell Migration and Invasion

  摘要：

  The P2X7 receptor (P2X7R) has been reported as a key mediator in inflammatory processes and cancer invasion/metastasis. In this study, we report the discovery of novel P2X7R antagonists and their functional activities as potential antimetastatic agents. Modifications of the hydantoin core-skeleton and the side chain substituents of the P2X7R antagonist 7 were performed. The structure activity relationships (SAR) and optimization demonstrated the importance of the sulfonyl group at the R-1 position and the substituted position and overall size of R-2 for P2X7R antagonism. The optimized novel analogues displayed potent P2X7 receptor antagonism (IC50 = 0.11-112 nM) along with significant suppressive effects on IL-1 beta release (IC50 = 0.32-210 nM). Moreover, representative antagonists (12g, 13k, and 17d) with imidazole and uracil core skeletons significantly inhibited the invasion of MDA-MB-231 triple negative breast cancer cells and cancer cell migration in a zebrafish xenograft model, suggesting the potential therapeutic application of these novel P2X7 antagonists to block metastatic cancer.

  DOI：

  10.1021/acs.jmedchem.5b01690