6-Bromo-8-diethoxyphosphoryl-2-(1-methoxy-3-methylbutyl)quinoline | 346418-63-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-Bromo-8-diethoxyphosphoryl-2-(1-methoxy-3-methylbutyl)quinoline
• 英文别名: 6-bromo-8-diethoxyphosphoryl-2-(1-methoxy-3-methylbutyl)quinoline
• CAS: 346418-63-1
• 化学式: C₁₉H₂₇BrNO₄P
• 分子量: 444.305
• InChiKey: GGKMSLDDBMOHGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-Bromo-8-diethoxyphosphoryl-2-(1-methoxy-3-methylbutyl)quinoline 在 正丁基锂 、 三甲基溴硅烷 、 钯 、 三溴氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [6-(4-{(R)-2-Benzotriazol-1-yl-3-[4-(difluoro-phosphono-methyl)-phenyl]-2-phenyl-propyl}-phenyl)-2-((S)-1-methoxy-3-methyl-butyl)-quinolin-8-yl]-phosphonic 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：

  diethyl 6-bromo-2-methyl-8-quinolylphosphonate 在 selenium(IV) oxide 、 sodium hydride 作用下， 生成 6-Bromo-8-diethoxyphosphoryl-2-(1-methoxy-3-methylbutyl)quinoline
  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

文献信息

• Phosphonic acid biaryl derivatives as inhibitors of protein tyrosine phosphatase 1B (PTP-1B)
  申请人：——

  公开号：US20020052346A1

  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 conditions.

  该发明涵盖了由公式I表示的新型化合物类别，这些化合物是PTP-1B酶的抑制剂。该发明还涵盖了制备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、肥胖症和与糖尿病相关的疾病。
• PHOSPHONIC ACID BIARYL DERIVATIVES AS INHIBITORS OF PROTEIN TYROSINE PHOSPHATASE 1B (PTP-1B)
  申请人：MERCK FROSST CANADA INC.

  公开号：EP1244677A1

  公开（公告）日：2002-10-02
• US6486141B2
  申请人：——

  公开号：US6486141B2

  公开（公告）日：2002-11-26
• [EN] PHOSPHONIC ACID BIARYL DERIVATIVES AS INHIBITORS OF PROTEIN TYROSINE PHOSPHATASE 1B (PTP-1B)<br/>[FR] DERIVES D'ACIDE PHOSPHONIQUE BIARYLE EN TANT QU'INHIBITEURS DE LA PROTEINE TYROSINE PHOSPHATASE 1B(PTP-1B)
  申请人：MERCK FROSST CANADA INC

  公开号：WO2001046203A1

  公开（公告）日：2001-06-28

  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, including diabetes, obesity, and diabetes-related conditions.
• 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.