di-(tert-butyl)-2-bromo-4-(bromomethyl) benzoylphosphonate | 345953-46-0

• 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: di-(tert-butyl)-2-bromo-4-(bromomethyl) benzoylphosphonate
• 英文别名: di(tert-butyl)-2-bromo-4-(bromomethyl)benzoylphosphonate；Bis[(2-methylpropan-2-yl)oxy]phosphoryl-[2-bromo-4-(bromomethyl)phenyl]methanone
• CAS: 345953-46-0
• 化学式: C₁₆H₂₃Br₂O₄P
• 分子量: 470.138
• InChiKey: LGOLXMLUKVLHJP-UHFFFAOYSA-N

物化性质

• 沸点：
  475.8±55.0 °C(Predicted)
• 密度：
  1.473±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  di-(tert-butyl)-2-bromo-4-(bromomethyl) benzoylphosphonate 在 potassium tert-butylate 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 四氢呋喃 为溶剂， 生成 di(tert-butyl)[2-bromo-4-(3-oxo-2,3-diphenylpropyl)phenyl](difluoro)methylphosphonate
  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
• 作为产物：
  描述：

  2-溴-4-甲基苯甲酸 在 manganese(IV) oxide 、 N-溴代丁二酰亚胺(NBS) 、 草酰氯 、 硼烷 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 生成 di-(tert-butyl)-2-bromo-4-(bromomethyl) benzoylphosphonate
  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

• Phosphonic acid derivatives as inhibitors of protein tyrosine phosphatase IB (PTP-IB)
  申请人：——

  公开号：US20020052344A1

  公开（公告）日：2002-05-02

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

  本发明包括一类新颖的化合物，这些化合物由公式I表示，是PTP-1B酶的抑制剂。 本发明还包括用于治疗或预防PTP-1B介导的疾病的药物组合物和方法，包括糖尿病、肥胖症和与糖尿病相关的疾病。
• Phosphonic acid derivatives as inhibitors of protein tyrosine phosphatase 1B (PTP-1B)
  申请人：——

  公开号：US20020058644A1

  公开（公告）日：2002-05-16

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

  该发明涵盖了由公式I代表的新型化合物类别，这些化合物是PTP-1B酶的抑制剂。该发明还涵盖了药物组合物和治疗或预防PTP-1B介导的疾病的方法，包括糖尿病、肥胖以及与糖尿病相关的疾病。
• Protein tyrosine phosphatase 1B (PTP-1B) inhibitors containing two ortho-substituted aromatic phosphonates
  申请人：——

  公开号：US20030114703A1

  公开（公告）日：2003-06-19

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

  本发明涵盖由公式I表示的新型化合物类，这些化合物是PTP-1B酶的抑制剂。本发明还涵盖了制备药物组合物的方法以及治疗或预防PTP-1B介导的疾病，包括糖尿病、肥胖症和与糖尿病相关的疾病的方法。
• PHOSPHONIC ACID DERIVATIVES AS INHIBITORS OF PROTEIN TYROSINE PHOSPHATASE 1B (PTP-1B)
  申请人：MERCK FROSST CANADA INC.

  公开号：EP1244678A1

  公开（公告）日：2002-10-02
• AROMATIC PHOSPHONATES AS PROTEIN TYROSINE PHOSPHATASE 1B (PTP-1B) INHIBITORS
  申请人：Merck Frosst Canada & Co.

  公开号：EP1242431A1

  公开（公告）日：2002-09-25