methyl 1-(3,3,3-trifluoropropyl)piperidine-4-carboxylate

• 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: methyl 1-(3,3,3-trifluoropropyl)piperidine-4-carboxylate
• 化学式: C₁₀H₁₆F₃NO₂
• mdl: MFCD21365215
• 分子量: 239.238
• InChiKey: PVFPDGKFWARJNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 1-(3,3,3-trifluoropropyl)piperidine-4-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到[1-(3,3,3-trifluoropropyl)piperidin-4-yl]methanol
  参考文献：
  名称：

  Design of fluorinated 5-HT4R antagonists: Influence of the basicity and lipophilicity toward the 5-HT4R binding affinities

  摘要：

  Analogues of potent 5-HT4R antagonists possessing a fluorinated N-alkyl chain have been synthesized in order to investigate the effect of the resulting change in basicity and lipophilicity on the affinity and selectivity profile. We demonstrate that for this series, the affinity is decreased with decreased basicity of the piperidine's nitrogen atom. In contrast, the resulting increase in lipophilicity has minimal impact on binding affinity and selectivity. 3,3,3-Trifluoropropyl and 4,4,4-trifluorobutyl derivatives 6d and 6e have shown to bind to the 5-HT4R while maintaining their pharmacological profile and selectivity toward other 5-HT receptors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.061
• 作为产物：
  描述：

  4-哌啶甲酸甲酯 、 3-溴-1，1，1-三氟丙烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以94%的产率得到methyl 1-(3,3,3-trifluoropropyl)piperidine-4-carboxylate
  参考文献：
  名称：

  Design of fluorinated 5-HT4R antagonists: Influence of the basicity and lipophilicity toward the 5-HT4R binding affinities

  摘要：

  Analogues of potent 5-HT4R antagonists possessing a fluorinated N-alkyl chain have been synthesized in order to investigate the effect of the resulting change in basicity and lipophilicity on the affinity and selectivity profile. We demonstrate that for this series, the affinity is decreased with decreased basicity of the piperidine's nitrogen atom. In contrast, the resulting increase in lipophilicity has minimal impact on binding affinity and selectivity. 3,3,3-Trifluoropropyl and 4,4,4-trifluorobutyl derivatives 6d and 6e have shown to bind to the 5-HT4R while maintaining their pharmacological profile and selectivity toward other 5-HT receptors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.061

文献信息

• [EN] AMINO-SUBSTITUTED ISOTHIAZOLES<br/>[FR] ISOTHIAZOLES AMINO-SUBSTITUÉS
  申请人：BAYER PHARMA AG

  公开号：WO2015113927A1

  公开（公告）日：2015-08-06

  The present invention relates to amino-substituted isothiazoles of general formula (I): in which A, R1 and R2 are as defined in the claims, to methods of preparing said compounds, to intermediate compounds useful for preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular of neoplasms, as a sole agent or in combination with other active ingredients.

  本发明涉及一般式(I)的氨基取代异噻唑化合物，其中A、R1和R2如权利要求中所定义，以及制备所述化合物的方法，用于制备所述化合物的有用中间体化合物，包含所述化合物的药物组合物和组合物，以及利用所述化合物制造用于治疗或预防疾病的药物组合物，特别是肿瘤，作为唯一药剂或与其他活性成分组合使用。
• Design of fluorinated 5-HT4R antagonists: Influence of the basicity and lipophilicity toward the 5-HT4R binding affinities
  作者：Clement Q. Fontenelle、Zhong Wang、Christine Fossey、Thomas Cailly、Bruno Linclau、Frederic Fabis

  DOI：10.1016/j.bmc.2013.08.061

  日期：2013.12

  Analogues of potent 5-HT4R antagonists possessing a fluorinated N-alkyl chain have been synthesized in order to investigate the effect of the resulting change in basicity and lipophilicity on the affinity and selectivity profile. We demonstrate that for this series, the affinity is decreased with decreased basicity of the piperidine's nitrogen atom. In contrast, the resulting increase in lipophilicity has minimal impact on binding affinity and selectivity. 3,3,3-Trifluoropropyl and 4,4,4-trifluorobutyl derivatives 6d and 6e have shown to bind to the 5-HT4R while maintaining their pharmacological profile and selectivity toward other 5-HT receptors. (C) 2013 Elsevier Ltd. All rights reserved.