5-bromo-2-(2,4-dichlorophenyl)-6-fluoro-2-(2-fluorophenyl)benzo[1,3]dioxole | 917751-96-3

• 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: 5-bromo-2-(2,4-dichlorophenyl)-6-fluoro-2-(2-fluorophenyl)benzo[1,3]dioxole
• 英文别名: 5-Bromo-2-(2,4-dichloro-phenyl)-6-fluoro-2-(2-fluoro-phenyl)-benzo[1,3]dioxole；5-bromo-2-(2,4-dichlorophenyl)-6-fluoro-2-(2-fluorophenyl)-1,3-benzodioxole
• CAS: 917751-96-3
• 化学式: C₁₉H₉BrCl₂F₂O₂
• 分子量: 458.086
• InChiKey: BDTRDCAEEXBYDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-吗啉碳酰氯 、 5-bromo-2-(2,4-dichlorophenyl)-6-fluoro-2-(2-fluorophenyl)benzo[1,3]dioxole 在 正丁基锂 作用下， 以 hexanes 、 乙醚 为溶剂， 反应 1.0h， 以73%的产率得到2-(2,4-dichlorophenyl)-6-fluoro-2-(2-fluorophenyl)-benzo[1,3]dioxol-5-yl-morpholin-4-yl-methanone
  参考文献：
  名称：

  Stereospecifically substituted benzo[1,3]dioxolyl derivatives

  摘要：

  本发明涉及式（I）的化合物，其中R1和R2如说明书和权利要求中所定义，并且其药学上可接受的盐，用作治疗活性物质。这些化合物可用于治疗和/或预防与CB1受体调节有关的疾病。

  公开号：

  US20060293318A1
• 作为产物：
  描述：

  4-溴-5-氟苯-1,2-二醇 、 2,4-二氯-1-[二氯-(2-氟苯基)甲基]苯 反应 0.33h， 以75%的产率得到5-bromo-2-(2,4-dichlorophenyl)-6-fluoro-2-(2-fluorophenyl)benzo[1,3]dioxole
  参考文献：
  名称：

  Stereospecifically substituted benzo[1,3]dioxolyl derivatives

  摘要：

  本发明涉及式（I）的化合物，其中R1和R2如说明书和权利要求中所定义，并且其药学上可接受的盐，用作治疗活性物质。这些化合物可用于治疗和/或预防与CB1受体调节有关的疾病。

  公开号：

  US20060293318A1

文献信息

• Stereospecifically substituted benzo[1,3]dioxolyl derivatives
  申请人：Frei Beat

  公开号：US20060293318A1

  公开（公告）日：2006-12-28

  The present invention relates to compounds of formula (I) wherein R 1 and R 2 are as defined in the description and claims, and pharmaceutically acceptable salts thereof, for use as therapeutically active substances. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with the modulation of CB1 receptors.

  本发明涉及式（I）的化合物，其中R1和R2如说明书和权利要求中所定义，并且其药学上可接受的盐，用作治疗活性物质。这些化合物可用于治疗和/或预防与CB1受体调节有关的疾病。
• STEREOSPECIFICALLY SUBSTITUTED BENZO[1,3]DIOXOLYL DERIVATIVES
  申请人：Frei Beat

  公开号：US20100056513A1

  公开（公告）日：2010-03-04

  The present invention relates to compounds of formula (I) wherein R 1 and R 2 are as defined in the description and claims, and pharmaceutically acceptable salts thereof, for use as therapeutically active substances. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with the modulation of CB1 receptors.

  本发明涉及式（I）的化合物，其中R1和R2如描述和权利要求中所定义，并且其药学上可接受的盐，用作治疗活性物质。这些化合物对于与CB1受体调节相关的疾病的治疗和/或预防非常有用。
• ( 6-FLU0R0-BENZ0[l, 3] DIOXOLYL) -MORPHOLIN-4-YL-METHANONES AND THEIR USE AS CBl LIGANDS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1896445B1

  公开（公告）日：2010-11-10
• [EN] ( 6-FLU0R0-BENZ0[l, 3] DIOXOLYL) -MORPHOLIN-4-YL-METHANONES AND THEIR USE AS CBl LIGANDS<br/>[FR] ( 6-FLUOROBENZO[1,3]DIOXOLYL)-MORPHOLIN-4-YL-MÉTHANONES ET LEUR EMPLOI EN TANT QUE LIGANDS DE CBI
  申请人：HOFFMANN LA ROCHE

  公开号：WO2006136502A1

  公开（公告）日：2006-12-28

  [EN] The present invention relates to compounds of formula (I) wherein R¹ and R² are as defined in the description and claims, and pharmaceutically acceptable salts thereof, for use as therapeutically active substances. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with the modulation of CBl receptors.
  [FR] La présente invention concerne des composés de formule (I) où R¹ et R² sont tels que définis dans la description et les revendications, ainsi que des sels de qualité pharmaceutique desdits composés, pour application en tant que substances thérapeutiques actives. Lesdits composés peuvent être employés dans le traitement prophylactique et/ou thérapeutique de maladies liées à la régulation des récepteurs CBI.
• Benzodioxoles: Novel Cannabinoid-1 Receptor Inverse Agonists for the Treatment of Obesity
  作者：Leo Alig、Jochem Alsenz、Mirjana Andjelkovic、Stefanie Bendels、Agnès Bénardeau、Konrad Bleicher、Anne Bourson、Pascale David-Pierson、Wolfgang Guba、Stefan Hildbrand、Dagmar Kube、Thomas Lübbers、Alexander V. Mayweg、Robert Narquizian、Werner Neidhart、Matthias Nettekoven、Jean-Marc Plancher、Cynthia Rocha、Mark Rogers-Evans、Stephan Röver、Gisbert Schneider、Sven Taylor、Pius Waldmeier

  DOI：10.1021/jm701487t

  日期：2008.4.1

  The application of the evolutionary fragment-based de novo design tool TOPology Assigning System (TOPAS), starting from a known CBIR (CB-1 receptor) ligand, followed by further refinement principles, including pharmacophore compliance, chemical tractability, and drug likeness, allowed the identification of benzodioxoles as a novel CB I R inverse agonist series. Extensive multidimensional optimization was rewarded by the identification of promising lead compounds, showing in vivo activity. These compounds reversed the CP-55940-induced hypothermia in Naval Medical Research Institute (NMRI) mice and reduced body-weight gain, as well as fat mass, in diet-induced obese Sprague-Dawley rats. Herein, we disclose the tools and strategies that were employed for rapid hit identification, synthesis and generation of structure-activity relationships, ultimately leading to the identification of (+)-[(R)-2-(2,4-dichloride-phenyl)-6-fluoro-2-(4-fluoro-phenyl)-benzo[1,3]dioxol-5-yl]-morpholin-4-yl-metha- none (R)-14g. Biochemical, pharmacokinetic, and pharmacodynamic characteristics of (R)-14g are discussed.