1-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)piperidin-4-amine | 590392-52-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)piperidin-4-amine
• 英文别名: 1-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethyl)-piperidine-4-ylamine；1-[[(1R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl]methyl]piperidin-4-amine
• CAS: 590392-52-2
• 化学式: C₁₅H₂₆N₂
• 分子量: 234.385
• InChiKey: HNERHTUHYVLHIB-JSGCOSHPSA-N

物化性质

• 沸点：
  314.4±42.0 °C(Predicted)
• 密度：
  1.003±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)piperidin-4-amine 、 2-氯-4-(3,4-二氯苯基)-1,3-噻唑 在 三乙胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 N-(4-(3,4-dichlorophenyl)thiazol-2-yl)-1-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)piperidin-4-amine
  参考文献：
  名称：

  Development of CXCR3 antagonists. Part 2: Identification of 2-amino(4-piperidinyl)azoles as potent CXCR3 antagonists

  摘要：

  Development of a lead series of piperidinylurea CXCR3 antagonists has led to the identification of molecules with alternative linkages which retain good potency. A novel 5-(piperidin-4-yl)amino-1,2,4-thiadiazole derivative was found to have satisfactory in vitro metabolic stability and to be orally bioavailable in mice, giving high plasma concentrations and a half life of 5.4 h. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.029
• 作为产物：
  描述：

  1-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethyl)-piperidine-4-yl-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 1-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)piperidin-4-amine
  参考文献：
  名称：

  Identification and structure–activity relationships of 1-aryl-3-piperidin-4-yl-urea derivatives as CXCR3 receptor antagonists

  摘要：

  The synthesis and biological evaluation of a series of 1-aryl-3-piperidin-4-yl-urea derivatives as small-molecule CXCR3 antagonists is described. SAR studies resulted in significant improvement of potency and physicochernical properties and established the key pharmacophore of the series, and led to the identification of 9t, which exhibits an IC50 of 16 nM in the GTP gamma S-35 functional assay. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.088

文献信息

• [EN] BICYCLIC HETEROAROMATIC DERIVATIVES AS MODULATORS OF CXCR3 FUNCTION<br/>[FR] DERIVES HETEROAROMATIQUES BICYCLIQUES EN TANT QUE MODULATEURS DE LA FONCTION CXCR3
  申请人：CELLTECH R&D LTD

  公开号：WO2005003127A1

  公开（公告）日：2005-01-13

  A class of 1-substituted 4-(benzothiazol-2-ylamino) piperidine derivatives and related heterocyclic compounds, being potent and selective modulators of the interaction between CXCR3 and its chemokine ligands, are accordingly of use in the treatment and/or prevention of conditions involving inappropriate T-cell trafficking, including inflammatory, autoimmune and immunoregulatory disorders.

  一类1-取代的4-(苯并噻唑-2-基氨基)哌啶衍生物及相关的杂环化合物，是CXCR3与其趋化因子配体相互作用的有效和选择性调节剂，因此可用于治疗和/或预防涉及不适当T细胞迁移的疾病，包括炎症性、自身免疫和免疫调节性疾病。
• [EN] SUBSTITUTED BENZIMIDAZOLES AS NOCICEPTIN RECEPTOR MODULATORS<br/>[FR] BENZIMIDAZOLES SUBSTITUÉS EN TANT QUE MODULATEURS D'UN RÉCEPTEUR DE NOCICEPTINE
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2014153529A1

  公开（公告）日：2014-09-25

  The invention provides modulators of the nociceptin receptor (NOP), including both agonists and antagonists. A compound of the invention can be a selective modulator of NOP with respect to the μ- and κ- opioid receptors (MOP and KOP), thus providing a therapeutic method for the treatment of conditions wherein selective NOP modulation is medically indicated and MOP or KOP modulation may be less desirable. A compound of the invention can be a NOP full agonist, partial agonist, inverse agonist, positive or negative allosteric modulator, or a functionally biased agonist. A compound of the invention can be used for the treatment of an anxiety state, post-traumatic stress disorder, addictive disorders (including overuse of alcohol, tobacco, and drugs of abuse such as cocaine, amphetamines, and opitates), misregulated food intake and/or energy expenditure, cough, sleep disorders, migraine, pain, depression, or neurodegenerative disorders such as Parkinsons disease or Alzheimers disease.

  该发明提供了辅料受体（NOP）的调节剂，包括激动剂和拮抗剂。该发明的化合物可以是NOP的选择性调节剂，相对于μ-和κ-阿片受体（MOP和KOP），因此提供了一种治疗方法，用于治疗需要选择性NOP调节而MOP或KOP调节可能不太理想的疾病。该发明的化合物可以是NOP的全激动剂、部分激动剂、逆激动剂、正或负变构调节剂，或功能性偏向激动剂。该发明的化合物可用于治疗焦虑状态、创伤后应激障碍、成瘾性障碍（包括滥用酒精、烟草和可卡因、安非他明和阿片类等药物）、食物摄入和/或能量消耗失调、咳嗽、睡眠障碍、偏头痛、疼痛、抑郁症，或帕金森病或阿尔茨海默病等神经退行性疾病的治疗。
• SUBSTITUTED BENZIMIDAZOLES AS NOCICEPTIN RECEPTOR MODULATORS
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：US20160052913A1

  公开（公告）日：2016-02-25

  The invention provides modulators of the nociceptin receptor (NOP), including both agonists and antagonists. A compound of the invention can be a selective modulator of NOP with respect to the μ- and κ-opioid receptors (MOP and KOP), thus providing a therapeutic method for the treatment of conditions wherein selective NOP modulation is medically indicated and MOP or KOP modulation may be less desirable. A compound of the invention can be a NOP full agonist, partial agonist, inverse agonist, positive or negative allosteric modulator, or a functionally biased agonist. A compound of the invention can be used for the treatment of an anxiety state, post-traumatic stress disorder, addictive disorders (including overuse of alcohol, tobacco, and drugs of abuse such as cocaine, amphetamines, and opitates), misregulated food intake and/or energy expenditure, cough, sleep disorders, grain, pain, depression, or neurodegenerative disorders such as Parkinsons disease or Alzheimers disease.

  本发明提供了诺西普针受体(NOP)的调节剂，包括激动剂和拮抗剂。本发明的化合物可以是NOP的选择性调节剂，相对于μ-和κ-阿片受体(MOP和KOP)，从而为治疗选择性NOP调节在医学上指示和MOP或KOP调节可能不太理想的情况提供治疗方法。本发明的化合物可以是NOP的全激动剂、部分激动剂、反向激动剂、正或负的变构调节剂，或功能偏向激动剂。本发明的化合物可用于治疗焦虑状态、创伤后应激障碍、成瘾性障碍(包括滥用酒精、烟草和滥用药物，如可卡因、安非他命和阿片类药物)、不当的食物摄入和/或能量消耗、咳嗽、睡眠障碍、谷物、疼痛、抑郁症或神经退行性疾病，如帕金森病或阿尔茨海默病的治疗。
• US9656994B2
  申请人：——

  公开号：US9656994B2

  公开（公告）日：2017-05-23
• Identification and structure–activity relationships of 1-aryl-3-piperidin-4-yl-urea derivatives as CXCR3 receptor antagonists
  作者：Daniel R. Allen、Amanda Bolt、Gayle A. Chapman、Roland L. Knight、Johannes W.G. Meissner、David A. Owen、Robert J. Watson

  DOI：10.1016/j.bmcl.2006.10.088

  日期：2007.2

  The synthesis and biological evaluation of a series of 1-aryl-3-piperidin-4-yl-urea derivatives as small-molecule CXCR3 antagonists is described. SAR studies resulted in significant improvement of potency and physicochernical properties and established the key pharmacophore of the series, and led to the identification of 9t, which exhibits an IC50 of 16 nM in the GTP gamma S-35 functional assay. (c) 2006 Elsevier Ltd. All rights reserved.