3-氯-5-(3-氯丙基)-10,11-二氢-5H-二苯并[b,f]氮杂卓 | 51551-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 中文名称: 3-氯-5-(3-氯丙基)-10,11-二氢-5H-二苯并[b,f]氮杂卓
• 中文别名: S-(4-叔-丁基苯甲基)(2-pentylpyridin-3-yl)硫代氨基甲酸酯
• 英文名称: 3-chloro-5-(3-chloropropyl)-10,11-dihydro-5H-dibenzo[b,f]azepine
• 英文别名: 3-chloro-5-(3-chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepine；2-chloro-11-(3-chloropropyl)-5,6-dihydrobenzo[b][1]benzazepine
• CAS: 51551-41-8
• 化学式: C₁₇H₁₇Cl₂N
• 分子量: 306.235
• InChiKey: RNNFGZMVJGWTEY-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-氯-5-(3-氯丙基)-10,11-二氢-5H-二苯并[b,f]氮杂卓 在 双氧水 、 potassium carbonate 作用下， 以 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 3-chloro-5-(3-((4-(trifluoromethoxy)phenyl)sulfonyl)propyl)-10,11-dihydro-5H-dibenzo[b,f]azepine
  参考文献：
  名称：

  Reengineered tricyclic anti-cancer agents

  摘要：

  The phenothiazine and dibenzazepine tricyclics are potent neurotropic drugs with a documented but underutilized anti-cancer side effect. Reengineering these agents (TFP, CPZ, CIP) by replacing the basic amine with a neutral polar functional group (e.g., RTC-1, RTC-2) abrogated their CNS effects as demonstrated by in vitro pharmacological assays and in vivo behavioral models. Further optimization generated several phenothiazines and dibenzazepines with improved anti-cancer potency, exemplified by RTC-5. This new lead demonstrated efficacy against a xenograft model of an EGFR driven cancer without the neurotropic effects exhibited by the parent molecules. Its effects were attributed to concomitant negative regulation of PI3K-AKT and RAS-ERK signaling. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.007
• 作为产物：
  描述：

  3-氯亚氨基二苄 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.5h， 生成 3-氯-5-(3-氯丙基)-10,11-二氢-5H-二苯并[b,f]氮杂卓
  参考文献：
  名称：

  Reengineered tricyclic anti-cancer agents

  摘要：

  The phenothiazine and dibenzazepine tricyclics are potent neurotropic drugs with a documented but underutilized anti-cancer side effect. Reengineering these agents (TFP, CPZ, CIP) by replacing the basic amine with a neutral polar functional group (e.g., RTC-1, RTC-2) abrogated their CNS effects as demonstrated by in vitro pharmacological assays and in vivo behavioral models. Further optimization generated several phenothiazines and dibenzazepines with improved anti-cancer potency, exemplified by RTC-5. This new lead demonstrated efficacy against a xenograft model of an EGFR driven cancer without the neurotropic effects exhibited by the parent molecules. Its effects were attributed to concomitant negative regulation of PI3K-AKT and RAS-ERK signaling. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.007

文献信息

• N-substituted azaheterocyclic carboxylic acids and esters thereof
  申请人：Novo Nordisk A/S

  公开号：US06239148B1

  公开（公告）日：2001-05-29

  The present invention relates to novel N-substituted azaheterocyclic carboxylic acids and esters thereof in which a substituted alkyl chain forms part of the N-substituent or salts thereof, to methods for their preparation, to compositions containing them, and to their use for the clinical treatment of painful, hyperalgesic and/or inflammatory conditions in which C-fibers play a pathophysiological role by eliciting neurogenic pain or inflammation.

  本发明涉及新型N-取代的氮杂环羧酸和其酯类，其中取代的烷基链构成N-取代基或其盐，以及它们的制备方法、含有它们的组合物和它们在临床治疗中的使用，用于治疗C纤维通过诱发神经源性疼痛或炎症在疼痛、过敏和/或炎症病症中发挥病理生理作用。
• N-substituted azaheterocyclic carboxylic acids and their use
  申请人：Novo Nordisk A/S

  公开号：US06613791B1

  公开（公告）日：2003-09-02

  N-substituted azaheterocycyclic carboxylic acids and esters thereof of the formula I wherein Z, X, R1, R2 and r are defined in the specification. Compositions thereof and methods for preparing the compounds are disclosed. The compounds are useful for clinical treatment of painful, hyperalgesic and/or inflammatory conditions in which C-fibers play a pathophysiological role by eliciting neurogenic pain or inflammations.

  本发明公开了式I中Z、X、R1、R2和r在说明书中定义的N-取代的杂环羧酸及其酯类。公开了这些化合物的组成及其制备方法。这些化合物在临床治疗C纤维通过引起神经源性疼痛或炎症所起的病理生理作用的疼痛、高敏感和/或炎症病症中非常有用。
• Tricyclic compounds in treating hyperalgesic conditions and NIDDM
  申请人：Novo Nordisk A/S

  公开号：US05962449A1

  公开（公告）日：1999-10-05

  The present invention relates to novel N-substituted amino acids and esters thereof in which a substituted alkyl chain forms part of the N-substituent or salts thereof, to methods for their preparation, to compositions containing them, and to their use for the clinical treatment of painful, hyperalgesic and/or inflammatory conditions in which C-fibers play a pathophysiological role by eliciting neurogenic pain or inflammation.

  本发明涉及新型N-取代氨基酸及其酯，其中取代烷基链形成N取代基的一部分，或其盐，以及其制备方法、含有它们的组合物，以及它们在临床治疗疼痛、高痛感和/或炎症病症中的应用，其中C纤维通过引起神经源性疼痛或炎症发挥病理生理作用。
• HETEROCYCLIC COMPOUNDS FOR TREATING DIABETES
  申请人：NOVO NORDISK A/S

  公开号：EP0820443B1

  公开（公告）日：2001-09-19
• US06071901
  申请人：——

  公开号：——

  公开（公告）日：——