[4-({[(Benzyl-methyl-carbamoyl)-methyl]-amino}-methyl)-phenoxy]-acetic acid tert-butyl ester | 863977-38-2

• 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: [4-({[(Benzyl-methyl-carbamoyl)-methyl]-amino}-methyl)-phenoxy]-acetic acid tert-butyl ester
• CAS: 863977-38-2
• 化学式: C₂₃H₃₀N₂O₄
• 分子量: 398.502
• InChiKey: NHXMELPFFUUTTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  67.87
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [4-({[(Benzyl-methyl-carbamoyl)-methyl]-amino}-methyl)-phenoxy]-acetic acid tert-butyl 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-({[(Benzyl-methyl-carbamoyl)-methyl]-[4-(difluoro-phosphono-methyl)-benzyl]-amino}-methyl)-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：

  N-methyl-N-benzylglycinamide 在 三乙酰氧基硼氢化钠 作用下， 以 甲醇 为溶剂， 生成 [4-({[(Benzyl-methyl-carbamoyl)-methyl]-amino}-methyl)-phenoxy]-acetic acid tert-butyl 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