diethyl [3-bromo-7-(bromomethyl)-2-naphthyl](difluoro)methylphosphonate | 1042170-62-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: diethyl [3-bromo-7-(bromomethyl)-2-naphthyl](difluoro)methylphosphonate
• 英文别名: 2-bromo-6-(bromomethyl)-3-[diethoxyphosphoryl(difluoro)methyl]naphthalene
• CAS: 1042170-62-6
• 化学式: C₁₆H₁₇Br₂F₂O₃P
• 分子量: 486.088
• InChiKey: GMPXSKDEGKICJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl [3-bromo-7-(bromomethyl)-2-naphthyl](difluoro)methylphosphonate 在 N-甲基吗啉氧化物 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 diethyl (3-bromo-7-formyl-2-naphthyl)(difluoro)methylphosphonate
  参考文献：
  名称：

  WO2008/89581

  摘要：

  公开号：
• 作为产物：
  描述：

  diethyl (3-bromo-7-methyl-2-naphthyl)(difluoro)methylphosphonate 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 生成 diethyl [3-bromo-7-(bromomethyl)-2-naphthyl](difluoro)methylphosphonate
  参考文献：
  名称：

  Discovery of [(3-bromo-7-cyano-2-naphthyl)(difluoro)methyl]phosphonic acid, a potent and orally active small molecule PTP1B inhibitor

  摘要：

  A series of quinoline/naphthalene-difluoromethylphosphonates were prepared and were found to be potent PTP1B inhibitors. Most of these compounds bearing polar functionalities or large lipophilic residues did not show appreciable oral bioavailability in rodents while small and less polar analogs displayed moderate to good oral bioavailability. The title compound was found to have the best overall potency and pharmacokinetic profile and was found to be efficacious in animal models of diabetes and cancer.

  DOI：

  10.1016/j.bmcl.2008.04.064

文献信息

• Discovery of Orally Active, Potent, and Selective Benzotriazole-Based PTP1B Inhibitors
  作者：Dipam Patel、Mukul Jain、Shailesh R. Shah、Rajesh Bahekar、Pradip Jadav、Brijesh Darji、Yernaidu Siriki、Debdutta Bandyopadhyay、Amit Joharapurkar、Samadhan Kshirsagar、Harilal Patel、Mubeen Shaikh、Kalapatapu V. V. M. Sairam、Pankaj Patel

  DOI：10.1002/cmdc.201100077

  日期：2011.6.6

  A two‐hand grasp on one enzyme: A novel series of dual‐site benzotriazole derivatives are reported as potent PTP1B inhibitors. Some of the test compounds exhibit good selectivity for PTP1B over various other PTPs, including TCPTP (in vitro), and the lead compound 10 h shows excellent antidiabetic activity (in vivo).

  对一种酶的双手掌握：据报道，一系列新型的双位苯并三唑衍生物是有效的PTP1B抑制剂。一些测试化合物对PTP1B的选择性优于其他各种PTP，包括TCPTP（体外），并且先导化合物10 h显示出出色的抗糖尿病活性（体内）。
• FUSED AROMATIC PTP-1B INHIBITORS
  申请人：Colucci John

  公开号：US20100022477A1

  公开（公告）日：2010-01-28

  The invention encompasses the novel class of compounds represented by the formula below, which are inhibitors of the PTP-1B enzyme. The invention also encompasses pharmaceutical compositions which include the compounds shown (Formula I) above and methods of treating or preventing PTP-1B mediated diseases, including diabetes.

  本发明涵盖了以下公式所代表的新型化合物类别，这些化合物是PTP-1B酶的抑制剂。本发明还涵盖了包括上述化合物（公式I）的制药组合物以及治疗或预防PTP-1B介导的疾病，包括糖尿病的方法。
• FUSED AROMATIC PTP-IB INHIBITORS
  申请人：COLUCCI John

  公开号：US20120178679A1

  公开（公告）日：2012-07-12

  The invention encompasses the novel class of compounds represented by the formula below, which are inhibitors of the PTP-1B enzyme. The invention also encompasses pharmaceutical compositions which include the compounds shown (Formula I) above and methods of treating or preventing PTP-1B mediated diseases, including diabetes.

  本发明涵盖了以下公式所代表的新型化合物类别，该类化合物是PTP-1B酶的抑制剂。本发明还涵盖了包括上述化合物（公式I）的制药组合物以及治疗或预防PTP-1B介导的疾病，包括糖尿病的方法。
• Fused aromatic PTP-1B inhibitors
  申请人：Colucci John

  公开号：US08481742B2

  公开（公告）日：2013-07-09

  The invention encompasses the novel class of compounds represented by the formula below, which are inhibitors of the PTP-1B enzyme. The invention also encompasses pharmaceutical compositions which include the compounds shown (Formula I) above and methods of treating or preventing PTP-1B mediated diseases, including diabetes.

  本发明涵盖了以下公式所代表的新型化合物类，这些化合物是PTP-1B酶的抑制剂。本发明还涵盖了包括上述化合物（公式I）的药物组合物以及治疗或预防PTP-1B介导的疾病，包括糖尿病的方法。
• US8168815B2
  申请人：——

  公开号：US8168815B2

  公开（公告）日：2012-05-01