1-[4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidin-1-yl]propan-1-one | 117796-54-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并环庚烷吡啶
• 英文名称: 1-[4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidin-1-yl]propan-1-one
• 英文别名: 8-chloro-11-(1-propionyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine；1-[4-(13-Chloro-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene)piperidin-1-yl]propan-1-one
• CAS: 117796-54-0
• 化学式: C₂₂H₂₃ClN₂O
• 分子量: 366.89
• InChiKey: YCUNEQYBXNSSJK-UHFFFAOYSA-N

物化性质

• 熔点：
  128-130 °C
• 沸点：
  555.7±50.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  氯雷他定 在 吡啶 、 氢氧化钾 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-[4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidin-1-yl]propan-1-one
  参考文献：
  名称：

  血小板活化因子和组胺的双重拮抗剂。鉴定N-酰基-4-（5,6-二氢-11H-苯并[5,6]环庚-[1,2-b]吡啶-11-亚吡啶）哌啶的双重活性的结构要求。

  摘要：

  DOI：

  10.1021/jm00105a069

文献信息

• Benzo(5,6)cycloheptapyridines, compositions and method of use
  申请人：SCHERING CORPORATION

  公开号：EP0270818A1

  公开（公告）日：1988-06-15

  Derivatives of benzo[5,6]cyclohepta pyridine, and pharmaceutically acceptable salts and solvates thereof are disclosed, which posses anti-allergic and anti-inflammatory activity. Methods for preparing and using the compounds are also described.

  本发明公开了苯并[5,6]环庚基吡啶的衍生物及其药学上可接受的盐和溶液，它们具有抗过敏和抗炎活性。还描述了制备和使用这些化合物的方法。
• Benzo(5,6)cycloheptapyridines, compositions and methods of use
  申请人：SCHERING CORPORATION

  公开号：EP0685476A1

  公开（公告）日：1995-12-06

  Derivatives of benzo[5,6]cyclohepta pyridine, and pharmaceutically acceptable salts and solvates thereof are disclosed, which possess anti-allergic and anti-inflammatory activity. Methods for preparing and using the compounds are also described.

  本发明公开了苯并[5,6]环庚基吡啶的衍生物及其药学上可接受的盐和溶液，它们具有抗过敏和抗炎活性。还描述了制备和使用这些化合物的方法。
• Synthesis and biological evaluation of novel derivatives of desloratadine
  作者：Shuai Mu、Xiao-Shuai Xie、Duan Niu、Da-Shuai Zhang、Deng-Ke Liu、Chang-Xiao Liu

  DOI：10.1016/j.cclet.2013.03.041

  日期：2013.6

  Series of novel derivatives of desloratadine designed as arginine vasopressin receptor antagonists were synthesized and structurally characterized by melting points, H-1 NMR and HRMS. Their in vivo diuretic activities were evaluated on rats, and several target compounds showed promising diuretic results, especially compounds 8,18,27 and 31. Further in vitro bonding assay and cAMP assay showed that these compounds had a higher affinity to vasopressin V2 receptor than Via receptor. Our studies indicated that desloratadine may be an active substructure for novel arginine vasopressin receptor antagonist development. (C) 2013 Chang-Xiao Liu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Loratadine and Analogues: Discovery and Preliminary Structure–Activity Relationship of Inhibitors of the Amino Acid Transporter B⁰AT2
  作者：Serena Cuboni、Christian Devigny、Bastiaan Hoogeland、Andrea Strasser、Sebastian Pomplun、Barbara Hauger、Georg Höfner、Klaus T. Wanner、Matthias Eder、Armin Buschauer、Florian Holsboer、Felix Hausch

  DOI：10.1021/jm501086v

  日期：2014.11.26

  B(0)AT2, encoded by the SLC6A15 gene, is a transporter for neutral amino acids that has recently been implicated in mood and metabolic disorders. It is predominantly expressed in the brain, but little is otherwise known about its function. To identify inhibitors for this transporter, we screened a library of 3133 different bioactive compounds. Loratadine, a clinically used histamine H1 receptor antagonist, was identified as a selective inhibitor of B(0)AT2 with an IC50 of 4 μM while being less active or inactive against several other members of the SLC6 family. Reversible inhibition of B(0)AT2 was confirmed by electrophysiology. A series of loratadine analogues were synthesized to gain insight into the structure-activity relationships. Our studies provide the first chemical tool for B(0)AT2.
• PIWINSKI, JOHN J.;GANGULY, ASHIT K.;GREEN, MICHAEL J.;VILLANI, FRANK J.;W+
  作者：PIWINSKI, JOHN J.、GANGULY, ASHIT K.、GREEN, MICHAEL J.、VILLANI, FRANK J.、W+

  DOI：——

  日期：——