[Difluoro-(4-{[(4-hydroxy-benzoyl)-(4-[1,2,3]thiadiazol-4-yl-benzyl)-amino]-methyl}-phenyl)-methyl]-phosphonic acid diethyl ester | 863977-17-7

• 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: [Difluoro-(4-{[(4-hydroxy-benzoyl)-(4-[1,2,3]thiadiazol-4-yl-benzyl)-amino]-methyl}-phenyl)-methyl]-phosphonic acid diethyl ester
• CAS: 863977-17-7
• 化学式: C₂₈H₂₈F₂N₃O₅PS
• 分子量: 587.584
• InChiKey: GYYMOMOJKUDVCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.07
• 重原子数：
  40.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  101.85
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [Difluoro-(4-{[(4-hydroxy-benzoyl)-(4-[1,2,3]thiadiazol-4-yl-benzyl)-amino]-methyl}-phenyl)-methyl]-phosphonic acid diethyl ester 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 生成 [Difluoro-(4-{[(4-hydroxy-benzoyl)-(4-[1,2,3]thiadiazol-4-yl-benzyl)-amino]-methyl}-phenyl)-methyl]-phosphonic 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：

  diethyl (difluoro(p-tolyl)methyl)phosphonate 在 N-溴代丁二酰亚胺(NBS) 、 乌洛托品 、 三乙酰氧基硼氢化钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 过氧化苯甲酰 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 氯仿 为溶剂， 生成 [Difluoro-(4-{[(4-hydroxy-benzoyl)-(4-[1,2,3]thiadiazol-4-yl-benzyl)-amino]-methyl}-phenyl)-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