4-(2-bromo-phenylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester | 1027143-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-(2-bromo-phenylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 4-(2-bromophenyl)sulfanylpiperidine-1-carboxylate
• CAS: 1027143-39-0
• 化学式: C₁₆H₂₂BrNO₂S
• 分子量: 372.326
• InChiKey: ZEKZBRSLHNBKOB-UHFFFAOYSA-N

物化性质

• 沸点：
  433.1±40.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-bromo-phenylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester 在 盐酸 、 sodium periodate 、 四(三苯基膦)钯 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙二醇二甲醚 、 水 、 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Towards the next generation of dual Bcl-2/Bcl-xL inhibitors

  摘要：

  Structural modifications of the left-hand side of compound 1 were identified which retained or improved potent binding to Bcl-2 and Bcl-x(L) in in vitro biochemical assays and had strong activity in an RS4;11 apoptotic cellular assay. For example, sulfoxide diastereomer 13 maintained good binding affinity and comparable cellular potency to 1 while improving aqueous solubility. The corresponding diastereomer (14) was significantly less potent in the cell, and docking studies suggest that this is due to a stereochemical preference for the R-S versus S-S sulfoxide. Appending a dimethylaminoethoxy side chain (27) adjacent to the benzylic position of the biphenyl moiety of 1 improved cellular activity by approximately threefold, and this activity was corroborated in cell lines overexpressing Bcl-2 and Bcl-x(L). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.036
• 作为产物：
  描述：

  2-溴硫代苯酚 、 4-溴-N-Boc-哌啶 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以100%的产率得到4-(2-bromo-phenylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Towards the next generation of dual Bcl-2/Bcl-xL inhibitors

  摘要：

  Structural modifications of the left-hand side of compound 1 were identified which retained or improved potent binding to Bcl-2 and Bcl-x(L) in in vitro biochemical assays and had strong activity in an RS4;11 apoptotic cellular assay. For example, sulfoxide diastereomer 13 maintained good binding affinity and comparable cellular potency to 1 while improving aqueous solubility. The corresponding diastereomer (14) was significantly less potent in the cell, and docking studies suggest that this is due to a stereochemical preference for the R-S versus S-S sulfoxide. Appending a dimethylaminoethoxy side chain (27) adjacent to the benzylic position of the biphenyl moiety of 1 improved cellular activity by approximately threefold, and this activity was corroborated in cell lines overexpressing Bcl-2 and Bcl-x(L). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.036

文献信息

• NOVEL PIPERAZINE DERIVATIVES AS INHIBITORS OF STEAROYL-CoA DESATURASE
  申请人：Sundaresan Kumar

  公开号：US20090239810A1

  公开（公告）日：2009-09-24

  The present invention relates to piperidine derivatives that act as inhibitors of stearoyl-CoA desaturase. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.

  本发明涉及作为硬脂酰辅酶A脱饱和酶抑制剂的哌啶衍生物。该发明还涉及制备这些化合物的方法、含有这些化合物的组合物，以及使用这些化合物进行治疗的方法。
• Piperidine derivatives as inhibitors of stearoyl-CoA desaturase
  申请人：——

  公开号：US08129376B2

  公开（公告）日：2012-03-06

  The present invention relates to piperidine derivatives that act as inhibitors of stearoyl-CoA desaturase. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.

  本发明涉及对硬脂酰辅酶A去饱和酶具有抑制作用的哌啶衍生物。本发明还涉及制备该化合物的方法，含有该化合物的组合物，以及使用该化合物进行治疗的方法。
• 4-(Phenylsulfonyl)piperidines:  Novel, Selective, and Bioavailable 5-HT_2A Receptor Antagonists
  作者：Stephen R. Fletcher、Frank Burkamp、Peter Blurton、Susan K. F. Cheng、Robert Clarkson、Desmond O'Connor、Daniel Spinks、Matthew Tudge、Monique B. van Niel、Smita Patel、Kerry Chapman、Rose Marwood、Sara Shepheard、Graham Bentley、Gina P Cook、Linda J Bristow、Jose L. Castro、Peter H. Hutson、Angus M. MacLeod

  DOI：10.1021/jm011030v

  日期：2002.1.1

  On the basis of a spirocyclic ether screening lead, a series of acyclic sulfones have been identifed as high-affinity, selective 5-HT2A receptor antagonists. Bioavailability lacking in the parent, 1-(2-(2,4-difluorophenyl)ethyl)-4-(phenylsulfonyl)piperidine (12), was introduced by using stability toward rat liver microsomes as a predictor of bioavailability. By this means, the 4-cyano- and 4-carboxamidophenylsulfonyl derivatives 26 and 31 were identified as orally bioavailable, brain-penetrant analogues suitable for evaluation in animal models. Bioavailability was also attainable by N substitution leading to the N-phenacyl derivative 35. IKr activity detected through counterscreening was reduced to insignificant levels in vivo with the latter compound.
• NOVEL PIPERIDINE DERIVATIVES AS INHIBITORS OF STEAROYL-COA DESATURASE
  申请人：Forest Laboratories Holdings Limited

  公开号：EP2268143A2

  公开（公告）日：2011-01-05
• US8129376B2
  申请人：——

  公开号：US8129376B2

  公开（公告）日：2012-03-06