4-[(4-氟苯基)磺酰基]哌啶 | 150221-22-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-[(4-氟苯基)磺酰基]哌啶
• 英文名称: 4-((4-fluorophenyl)-sulfonyl)-piperidine
• 英文别名: 4-((4-Fluorophenyl)sulfonyl)piperidine；4-(4-fluorophenyl)sulfonylpiperidine
• CAS: 150221-22-0
• 化学式: C₁₁H₁₄FNO₂S
• 分子量: 243.302
• InChiKey: WUWFTIGTTQLIMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-溴乙基)-2,4-二氟苯 、 4-[(4-氟苯基)磺酰基]哌啶 在 potassium carbonate 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 18.0h， 生成 1-(2,4-difluorophenethyl)-4-((4-fluorophenyl)sulfonyl)piperidine
  参考文献：
  名称：

  4-(Phenylsulfonyl)piperidines:  Novel, Selective, and Bioavailable 5-HT_2A Receptor Antagonists

  摘要：

  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.

  DOI：

  10.1021/jm011030v
• 作为产物：
  描述：

  1-氟-4-[(4-氟苯基)二硫烷基]苯 在 盐酸 、 aluminum oxide 、 Oxone 、 三丁基膦 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 为溶剂， 反应 69.0h， 生成 4-[(4-氟苯基)磺酰基]哌啶
  参考文献：
  名称：

  4-(Phenylsulfonyl)piperidines:  Novel, Selective, and Bioavailable 5-HT_2A Receptor Antagonists

  摘要：

  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.

  DOI：

  10.1021/jm011030v

文献信息

• TETRAHYDROPYRIDOPYRAZINES MODULATORS OF GPR6
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US20150175602A1

  公开（公告）日：2015-06-25

  The present invention provides compounds of formula I: which are useful as modulators of GPR6, pharmaceutical compositions thereof, methods for treatment of conditions associated with GPR6, processes for making the compounds and intermediates thereof.

  本发明提供了式I化合物： 这些化合物作为GPR6调节剂具有用途，包括相关的药物组合物、治疗与GPR6相关病症的方法、制备这些化合物及其中间体的工艺。
• Rational Design, Pharmacomodulation, and Synthesis of Dual 5-Hydroxytryptamine 7 (5-HT₇)/5-Hydroxytryptamine 2A (5-HT_2A) Receptor Antagonists and Evaluation by [¹⁸F]-PET Imaging in a Primate Brain
  作者：Emmanuel Deau、Elodie Robin、Raluca Voinea、Nathalie Percina、Grzegorz Satała、Adriana-Luminita Finaru、Agnès Chartier、Gilles Tamagnan、David Alagille、Andrzej J. Bojarski、Séverine Morisset-Lopez、Franck Suzenet、Gérald Guillaumet

  DOI：10.1021/acs.jmedchem.5b00874

  日期：2015.10.22

  We report the synthesis of 46 tertiary amine-bearing N-alkylated benzo[d]imidazol-2(3H)-ones, imidazo[4,5-b]pyridin-2(3H)-ones, imidazo[4,5-c]pyridin-2(3H)-ones, benzo[d]oxazol-2(3H)-ones, oxazolo[4,5-b]pyridin-2(3H)-ones and N,N′-dialkylated benzo[d]imidazol-2(3H)-ones. These compounds were evaluated against 5-HT7R, 5-HT2AR, 5-HT1AR, and 5-HT6R as potent dual 5-HT7/5-HT2A serotonin receptors ligands

  我们报告了46个含叔胺的N-烷基化苯并[ d ]咪唑-2（3 H）-ones，咪唑并[4,5 - b ]吡啶-2（3 H）-ones，咪唑并[4,5 ]的合成- ç ]吡啶-2（3 H ^） -酮，苯并[ d ]唑-2（3 H ^） -酮，恶唑并[4,5- b ]吡啶-2（3 H ^） -酮和ñ，ñ ' -二烷基化的苯并[ d ]咪唑-2（3 H）-ones。针对5-HT 7 R，5-HT 2A R，5-HT 1A R和5-HT 6评估了这些化合物R为有效的双重5-HT 7 / 5-HT 2A血清素受体配体。对芳香环及其取代基，烷基链长和叔胺的结构-活性关系进行了彻底的研究。1-（4-（4-（4-氟苯甲酰基）哌啶-1-基）丁基）-1 H-苯并[ d ]咪唑-2（3 H）-一（79）和1-（6-（4- （4-氟苯甲酰基）哌啶-1-基己基）-1 H-苯并[ d ]咪唑-2（3 H）-一（81）
• [EN] 4-ARYLSULPHONYLPIPERIDINE DERIVATIVES FOR ANTAGONISM OF THE 5-HT2A RECEPTOR<br/>[FR] DERIVES DE 4-ARYLSULPHONYLPIPERIDINE POUR L'ANTAGONISME DU RECEPTEUR DE 5-HT2A
  申请人：MERCK SHARP & DOHME

  公开号：WO2004101518A1

  公开（公告）日：2004-11-25

  Compounds of formula (I): are selective antagonists of the 5-HT2A receptor, and hence are useful in treatment of adverse conditions at the central nervous system, such as sleep disorders and schizophrenia.

  式(I)的化合物是5-HT2A受体的选择性拮抗剂，因此在治疗中枢神经系统的不良症状，如睡眠障碍和精神分裂症方面具有用处。
• [EN] PYRIDOPYRAZINES MODULATORS OF GPR6<br/>[FR] MODULATEURS PYRIDOPYRAZINES DE GPR6
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2015123505A1

  公开（公告）日：2015-08-20

  The present invention provides compounds of formula (I): [Formula should be entered here] which are useful as modulators of GPR6, pharmaceutical compositions thereof, methods for treatment of conditions associated with GPR6, processes for making the compounds and intermediates thereof.

  本发明提供了式（I）的化合物：[应在此处输入公式]，其作为GPR6调节剂是有用的，以及其药物组合物，治疗与GPR6相关疾病的方法，制备该化合物及其中间体的过程。
• [EN] PYRAZINES MODULATORS OF GPR6<br/>[FR] MODULATEURS DE PYRAZINES DE GPR6
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2015123533A1

  公开（公告）日：2015-08-20

  The present invention provides compounds of formula (I): which are useful as modulators of GPR6, pharmaceutical compositions thereof, methods for treatment of conditions associated with GPR6, processes for making the compounds and intermediates thereof.

  本发明提供了如下式（I）的化合物，这些化合物可作为GPR6的调节剂，以及与之相关的药物组合物、治疗与GPR6相关疾病的方法、制备这些化合物及其中间体的工艺。