1-(3,4-Difluorobenzyl)-1H-benzotriazole | 261176-52-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 1-(3,4-Difluorobenzyl)-1H-benzotriazole
• 英文别名: 1-[(3,4-difluorophenyl)methyl]benzotriazole
• CAS: 261176-52-7
• 化学式: C₁₃H₉F₂N₃
• 分子量: 245.231
• InChiKey: QRJIKMNQORCNQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3,4-Difluorobenzyl)-1H-benzotriazole 在 正丁基锂 、 三甲基溴硅烷 作用下， 生成 (4-{2-Benzotriazol-1-yl-2-(3,4-difluorophenyl)-3-[4-(difluorophosphonomethyl)phenyl]propyl}phenyl)difluoromethylphosphonic acid
  参考文献：
  名称：

  Structure based design of a series of potent and selective non peptidic PTP-1B inhibitors

  摘要：

  A series of benzotriazole phenyldifluoromethylphosphonic acids were found to be potent PTP-1B inhibitors. Molecular modeling on the X-ray crystal structure of the lead structure led to the design of potent PTP-1B inhibitors that show moderate selectivity against TC-PTP, a very closely related protein tyrosine phosphatase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.076
• 作为产物：
  描述：

  T406石油添加剂 、 3,4-二氟溴苄 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以1.6 g (65%)的产率得到1-(3,4-Difluorobenzyl)-1H-benzotriazole
  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表示的新型化合物类，这些化合物是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

文献信息

• 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表示的新型化合物类，这些化合物是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。
• PHOSPHONIC ACID DERIVATIVES AS INHIBITORS OF PTP-1B
  申请人：Merck Frosst Canada & Co.

  公开号：EP1115729A1

  公开（公告）日：2001-07-18
• US6174874B1
  申请人：——

  公开号：US6174874B1

  公开（公告）日：2001-01-16
• [EN] PHOSPHONIC ACIDS DERIVATIVES AS INHIBITORS OF PTP-1B<br/>[FR] DERIVES DE L'ACIDE PHOSPHONIQUE UTILES COMME INHIBITEURS DE LA PTP-1B
  申请人：MERCK FROSST CANADA INC

  公开号：WO2000017211A1

  公开（公告）日：2000-03-30

  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.
• Structure based design of a series of potent and selective non peptidic PTP-1B inhibitors
  作者：Cheuk K. Lau、Christopher I. Bayly、Jacques Yves Gauthier、Chun Sing Li、Michel Therien、Ernest Asante-Appiah、Wanda Cromlish、Yves Boie、Farnaz Forghani、Sylvie Desmarais、Qingping Wang、Kathryn Skorey、Deena Waddleton、Paul Payette、Chidambaram Ramachandran、Brian P. Kennedy、Giovana Scapin

  DOI：10.1016/j.bmcl.2003.11.076

  日期：2004.2

  A series of benzotriazole phenyldifluoromethylphosphonic acids were found to be potent PTP-1B inhibitors. Molecular modeling on the X-ray crystal structure of the lead structure led to the design of potent PTP-1B inhibitors that show moderate selectivity against TC-PTP, a very closely related protein tyrosine phosphatase. (C) 2004 Elsevier Ltd. All rights reserved.