[(4-Bromomethyl-2-methoxy-phenyl)-difluoro-methyl]-phosphonic acid diethyl ester | 884646-49-5

• 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-Bromomethyl-2-methoxy-phenyl)-difluoro-methyl]-phosphonic acid diethyl ester
• CAS: 884646-49-5
• 化学式: C₁₃H₁₈BrF₂O₄P
• 分子量: 387.158
• InChiKey: HDYOKBIXFWHQFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(4-Bromomethyl-2-methoxy-phenyl)-difluoro-methyl]-phosphonic acid diethyl ester 在 三甲基溴硅烷 、 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 {4-[[4-(Difluoro-phosphono-methyl)-3-methoxy-benzyl]-(4-dimethylsulfamoyl-benzyl)-sulfamoyl]-phenoxy}-acetic acid
  参考文献：
  名称：

  Discovery and structure–activity relationships of novel sulfonamides as potent PTP1B inhibitors

  摘要：

  A series of novel sulfonamides containing a single difluoromethylene-phosphonate group were discovered to be potent inhibitors of protein tyrosine phosphatase 1B. Structure-activity relationships around the scaffold were investigated, leading to the identification of compounds with IC50 or K-i values in the low nanomolar range. These sulfonamide-based inhibitors exhibit 100 and 30 times higher inhibitory activity than the corresponding tertiary amines and carboxamides, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.061
• 作为产物：
  描述：

  [Difluoro-(2-methoxy-4-methyl-phenyl)-methyl]-phosphonic acid diethyl ester 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 生成 [(4-Bromomethyl-2-methoxy-phenyl)-difluoro-methyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Discovery and structure–activity relationships of novel sulfonamides as potent PTP1B inhibitors

  摘要：

  A series of novel sulfonamides containing a single difluoromethylene-phosphonate group were discovered to be potent inhibitors of protein tyrosine phosphatase 1B. Structure-activity relationships around the scaffold were investigated, leading to the identification of compounds with IC50 or K-i values in the low nanomolar range. These sulfonamide-based inhibitors exhibit 100 and 30 times higher inhibitory activity than the corresponding tertiary amines and carboxamides, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.061