tetraethyl (((5-benzylpyridin-3-yl)amino)methylene)bis(phosphonate) | 1401111-05-4

• 英文名称: tetraethyl (((5-benzylpyridin-3-yl)amino)methylene)bis(phosphonate)
• CAS: 1401111-05-4
• 化学式: C₂₁H₃₂N₂O₆P₂
• 分子量: 470.442
• InChiKey: SSHJDBAWYXCGBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  31.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  95.98
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tetraethyl (((5-benzylpyridin-3-yl)amino)methylene)bis(phosphonate) 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 以79%的产率得到[[(5-Benzylpyridin-3-yl)amino]-phosphonomethyl]phosphonic acid
  参考文献：
  名称：

  Design of potent bisphosphonate inhibitors of the human farnesyl pyrophosphate synthase via targeted interactions with the active site ‘capping’ phenyls

  摘要：

  Nitrogen-containing bisphosphonates (N-BPs) are potent active site inhibitors of the human farnesyl pyrophosphate synthase (hFPPS) and valuable human therapeutics for the treatment of bone-related malignancies. N-BPs are also useful in combination chemotherapy for patients with breast, prostate and multiple myeloma cancers. A structure-based approach was employed in order to design inhibitors that exhibit higher lipophilicity and better occupancy for the GPP sub-pocket of hFPPS than the current therapeutic drugs. These novel analogs were designed to bind deeper into the GPP sub-pocket by displacing the side chains of the 'capping' residue Phe 113 and engaging in favorable p-interactions with the side chain of Phe112. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.019
• 作为产物：
  描述：

  tetraethyl (((5-bromopyridin-3-yl)amino)methylene)bis(phosphonate) 、 potassium benzyltrifluoroborate 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以55%的产率得到tetraethyl (((5-benzylpyridin-3-yl)amino)methylene)bis(phosphonate)
  参考文献：
  名称：

  Design of potent bisphosphonate inhibitors of the human farnesyl pyrophosphate synthase via targeted interactions with the active site ‘capping’ phenyls

  摘要：

  Nitrogen-containing bisphosphonates (N-BPs) are potent active site inhibitors of the human farnesyl pyrophosphate synthase (hFPPS) and valuable human therapeutics for the treatment of bone-related malignancies. N-BPs are also useful in combination chemotherapy for patients with breast, prostate and multiple myeloma cancers. A structure-based approach was employed in order to design inhibitors that exhibit higher lipophilicity and better occupancy for the GPP sub-pocket of hFPPS than the current therapeutic drugs. These novel analogs were designed to bind deeper into the GPP sub-pocket by displacing the side chains of the 'capping' residue Phe 113 and engaging in favorable p-interactions with the side chain of Phe112. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.019