2,2-Di{4-[(di-tert-butoxyphosphoryl)(difluoro)methyl]benzyl}malonic Acid, Benzyl Methyl Ester | 261176-01-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2,2-Di{4-[(di-tert-butoxyphosphoryl)(difluoro)methyl]benzyl}malonic Acid, Benzyl Methyl Ester
• 英文别名: 3-O-benzyl 1-O-methyl 2,2-bis[[4-[bis[(2-methylpropan-2-yl)oxy]phosphoryl-difluoromethyl]phenyl]methyl]propanedioate
• CAS: 261176-01-6
• 化学式: C₄₃H₅₈F₄O₁₀P₂
• 分子量: 872.869
• InChiKey: BSTUTPUVZWQHLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  59
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2,2-Di{4-[(di-tert-butoxyphosphoryl)(difluoro)methyl]benzyl}malonic Acid, Benzyl Methyl Ester 在 钯 氢气 、 silica gel 、 Ethyl acetate hexane acetic acid 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以to give 0.1 g of the title compound as a yellow syrup的产率得到2,2-Di{4-[(di-tert-butoxyphosphoryl)(difluoro)methyl]benzyl}-3-methoxy-3-oxopropanoic acid
  参考文献：
  名称：

  Phosphonic acids derivatives as inhibitors of protein tyrosine phosphate 1B (PTP-1B)

  摘要：

  该发明涵盖了由公式I所代表的新型化合物类，它们是PTP-1B酶的抑制剂。该发明还涵盖了制药组合物和治疗或预防PTP-1B介导疾病的方法。

  公开号：

  US06174874B1
• 作为产物：
  描述：

  苄基丙二酸二甲酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2,2-Di{4-[(di-tert-butoxyphosphoryl)(difluoro)methyl]benzyl}malonic Acid, Benzyl Methyl Ester
  参考文献：
  名称：

  The development of potent non-peptidic PTP-1B inhibitors

  摘要：

  The SAR from our peptide libraries was exploited to design a series of potent deoxybenzoin PTP-1B inhibitors. The introduction of an ortho bromo substituent next to the difluoromethylphosphonate warhead gave up to 20-fold increase in potency compared to the desbromo analogues. In addition, these compounds were orally bioavailable and active in the animal models of non-insulin dependent diabetes mellitus (NIDDM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.048

文献信息

• The development of potent non-peptidic PTP-1B inhibitors
  作者：Claude Dufresne、Patrick Roy、Zhaoyin Wang、Ernest Asante-Appiah、Wanda Cromlish、Yves Boie、Farnaz Forghani、Sylvie Desmarais、Qingping Wang、Kathryn Skorey、Deena Waddleton、Chidambaram Ramachandran、Brian P. Kennedy、Lijing Xu、Robert Gordon、Chi Chung Chan、Yves Leblanc

  DOI：10.1016/j.bmcl.2003.11.048

  日期：2004.2

  The SAR from our peptide libraries was exploited to design a series of potent deoxybenzoin PTP-1B inhibitors. The introduction of an ortho bromo substituent next to the difluoromethylphosphonate warhead gave up to 20-fold increase in potency compared to the desbromo analogues. In addition, these compounds were orally bioavailable and active in the animal models of non-insulin dependent diabetes mellitus (NIDDM). (C) 2004 Elsevier Ltd. All rights reserved.
• Phosphonic acids derivatives as inhibitors of protein tyrosine phosphate 1B (PTP-1B)
  申请人：Merck Frosst Canada & Co.

  公开号：US06174874B1

  公开（公告）日：2001-01-16

  The invention encompasses the novel class of compounds represented by formula I which are inhibitors of the PTP-1B enzyme. The invention also encompasses pharmaceutical compositions and methods of treating or preventing PTP-1B mediated diseases.

  该发明涵盖了由公式I所代表的新型化合物类，它们是PTP-1B酶的抑制剂。该发明还涵盖了制药组合物和治疗或预防PTP-1B介导疾病的方法。