4-(3-fluorobenzyloxy)benzene-1-sulfonyl chloride | 625814-26-8

• 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: 4-(3-fluorobenzyloxy)benzene-1-sulfonyl chloride
• 英文别名: 4-[(3-Fluorophenyl)methoxy]benzenesulfonyl chloride
• CAS: 625814-26-8
• 化学式: C₁₃H₁₀ClFO₃S
• mdl: MFCD09809221
• 分子量: 300.738
• InChiKey: RDLBDJGCDHCZQM-UHFFFAOYSA-N

物化性质

• 沸点：
  424.3±25.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3-fluorobenzyloxy)benzene-1-sulfonyl chloride 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 N-(tert-butyldimethylsilyloxy)-2-(4-(3-fluorobenzyloxy)phenylsulfonamido)acetamide
  参考文献：
  名称：

  Selective Arylsulfonamide Inhibitors of ADAM-17: Hit Optimization and Activity in Ovarian Cancer Cell Models

  摘要：

  Activated leukocyte cell adhesion molecule (ALCAM) is expressed at the surface of epithelial ovarian cancer (EOC) cells and is released in a soluble form (sALCAM) by ADAM-17-mediated shedding. This process is relevant to EOC cell motility and invasiveness, which is reduced by inhibitors of ADAM-17. In addition, ADAM-17 plays a key role in EGFR signaling and thus may represent a useful target in anticancer therapy. Herein we report our hit optimization effort to identify potent and selective ADAM-17 inhibitors, starting with previously identified inhibitor 1. A new series of secondary sulfonamido-based hydroxamates was designed and synthesized. The biological activity of the newly synthesized compounds was tested in vitro on isolated enzymes and human EOC cell lines. The optimization process led to compound 21, which showed an IC50 of 1.9 nivi on ADAM-17 with greatly increased selectivity. This compound maintained good inhibitory properties on sALCAM shedding in several in vitro assays.

  DOI：

  10.1021/jm4011753
• 作为产物：
  描述：

  sodium p-hydroxybenzenesulfonate 在 草酰氯 、 sodium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 48.0h， 生成 4-(3-fluorobenzyloxy)benzene-1-sulfonyl chloride
  参考文献：
  名称：

  Selective Arylsulfonamide Inhibitors of ADAM-17: Hit Optimization and Activity in Ovarian Cancer Cell Models

  摘要：

  Activated leukocyte cell adhesion molecule (ALCAM) is expressed at the surface of epithelial ovarian cancer (EOC) cells and is released in a soluble form (sALCAM) by ADAM-17-mediated shedding. This process is relevant to EOC cell motility and invasiveness, which is reduced by inhibitors of ADAM-17. In addition, ADAM-17 plays a key role in EGFR signaling and thus may represent a useful target in anticancer therapy. Herein we report our hit optimization effort to identify potent and selective ADAM-17 inhibitors, starting with previously identified inhibitor 1. A new series of secondary sulfonamido-based hydroxamates was designed and synthesized. The biological activity of the newly synthesized compounds was tested in vitro on isolated enzymes and human EOC cell lines. The optimization process led to compound 21, which showed an IC50 of 1.9 nivi on ADAM-17 with greatly increased selectivity. This compound maintained good inhibitory properties on sALCAM shedding in several in vitro assays.

  DOI：

  10.1021/jm4011753

文献信息

• Efficient Route for the Preparation of Benzyloxy-Substituted Benzenesulfonyl Chlorides from Mercaptophenols
  作者：Coline Jumeaux、David G. Cooper、Bruce T. Brown、Ian T. Forbes、Vincenzo Garzya

  DOI：10.1080/00397911.2010.492461

  日期：2011.5.4

  [image omitted] A consistently high-yielding route has been developed for the preparation of benzyloxybenzenesulfonyl chlorides from mercaptophenols. This route allows rapid preparation of intermediates for array chemistry.
• Selective Arylsulfonamide Inhibitors of ADAM-17: Hit Optimization and Activity in Ovarian Cancer Cell Models
  作者：Elisa Nuti、Francesca Casalini、Salvatore Santamaria、Marina Fabbi、Grazia Carbotti、Silvano Ferrini、Luciana Marinelli、Valeria La Pietra、Ettore Novellino、Caterina Camodeca、Elisabetta Orlandini、Susanna Nencetti、Armando Rossello

  DOI：10.1021/jm4011753

  日期：2013.10.24

  Activated leukocyte cell adhesion molecule (ALCAM) is expressed at the surface of epithelial ovarian cancer (EOC) cells and is released in a soluble form (sALCAM) by ADAM-17-mediated shedding. This process is relevant to EOC cell motility and invasiveness, which is reduced by inhibitors of ADAM-17. In addition, ADAM-17 plays a key role in EGFR signaling and thus may represent a useful target in anticancer therapy. Herein we report our hit optimization effort to identify potent and selective ADAM-17 inhibitors, starting with previously identified inhibitor 1. A new series of secondary sulfonamido-based hydroxamates was designed and synthesized. The biological activity of the newly synthesized compounds was tested in vitro on isolated enzymes and human EOC cell lines. The optimization process led to compound 21, which showed an IC50 of 1.9 nivi on ADAM-17 with greatly increased selectivity. This compound maintained good inhibitory properties on sALCAM shedding in several in vitro assays.