ethyl 1-(benzylsulfonyl)piperidine-2-carboxylate | 1039510-65-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 1-(benzylsulfonyl)piperidine-2-carboxylate
• 英文别名: ethyl 1-benzylsulfonylpiperidine-2-carboxylate
• CAS: 1039510-65-0
• 化学式: C₁₅H₂₁NO₄S
• 分子量: 311.402
• InChiKey: LVCFWVYKKRGZFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 1-(benzylsulfonyl)piperidine-2-carboxylate 在 lithium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 以94%的产率得到1-(benzylsulfonyl)piperidine-2-carboxylic acid
  参考文献：
  名称：

  Pipecolate-sulfonamides for treatment of psychiatric disorders

  摘要：

  本发明涉及具有吡啶甲酸磺酰胺骨架的化合物，这些化合物的药用盐以及含有至少一种这些化合物的药用载体、赋形剂和/或稀释剂的药物组合物。所述的吡啶甲酸磺酰胺化合物可用于预防和/或治疗精神障碍和神经退行性疾病、障碍和症状。

  公开号：

  EP2610245A1
• 作为产物：
  描述：

  六氢吡啶-alpha-羧酸 在 氯化亚砜 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 ethyl 1-(benzylsulfonyl)piperidine-2-carboxylate
  参考文献：
  名称：

  Development, synthesis and structure–activity-relationships of inhibitors of the macrophage infectivity potentiator (Mip) proteins of Legionella pneumophila and Burkholderia pseudomallei

  摘要：

  The bacteria Burkholderia pseudomallei and Legionella pneumophila cause severe diseases like melioidosis and Legionnaire's disease with high mortality rates despite antibiotic treatment. Due to increasing antibiotic resistances against these and other Gram-negative bacteria, alternative therapeutical strategies are in urgent demand. As a virulence factor, the macrophage infectivity potentiator (Mip) protein constitutes an attractive target. The Mip proteins of B. pseudomallei and L. pneumophila exhibit peptidyl-prolyl cis/trans isomerase (PPIase) activity and belong to the PPIase superfamily. In previous studies, the pipecolic acid moiety proved to be a valuable scaffold for inhibiting this PPIase activity. Thus, a library of pipecolic acid derivatives was established guided by structural information and computational analyses of the binding site and possible binding modes. Stability and toxicity considerations were taken into account in iterative extensions of the library. Synthesis and evaluation of the compounds in PPlase assays resulted in highly active inhibitors. The activities can be interpreted in terms of a common binding mode obtained by docking calculations. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.08.025

文献信息

• [EN] PIPECOLATE-SULFONAMIDES FOR TREATMENT OF PSYCHIATRIC DISORDERS<br/>[FR] PIPÉCOLATE-SULFONAMIDES POUR LE TRAITEMENT DE TROUBLES PSYCHIATRIQUES
  申请人：MAX PLANCK GESELLSCHAFT

  公开号：WO2013097947A1

  公开（公告）日：2013-07-04

  The present invention relates to compounds having a pipecolate sulfonamide scaffold, pharmaceutically acceptable salts of these compounds and pharmaceutical compositions containing at least one of these compounds together with pharmaceutically acceptable carrier, excipient and/or diluents. Said pipecolate sulfonamide compounds can be used for prophylaxis and/or treatment of psychiatric disorders and neurodegenerative diseases, disorders and conditions.

  本发明涉及具有吡哌酸磺胺基骨架的化合物，这些化合物的药用盐以及含有至少一种这些化合物的药用载体、赋形剂和/或稀释剂的药物组合物。所述的吡哌酸磺胺基化合物可用于预防和/或治疗精神障碍和神经退行性疾病、紊乱和状况。
• Pipecolate-sulfonamides for treatment of psychiatric disorders
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP2610245A1

  公开（公告）日：2013-07-03

  The present invention relates to compounds having a pipecolate sulfonamide scaffold, pharmaceutically acceptable salts of these compounds and pharmaceutical compositions containing at least one of these compounds together with pharmaceutically acceptable carrier, excipient and/or diluents. Said pipecolate sulfonamide compounds can be used for prophylaxis and/or treatment of psychiatric disorders and neurodegenerative diseases, disorders and conditions.

  本发明涉及具有吡啶甲酸磺酰胺骨架的化合物，这些化合物的药用盐以及含有至少一种这些化合物的药用载体、赋形剂和/或稀释剂的药物组合物。所述的吡啶甲酸磺酰胺化合物可用于预防和/或治疗精神障碍和神经退行性疾病、障碍和症状。
• PIPECOLATE-SULFONAMIDES FOR TREATMENT OF PSYCHIATRIC DISORDERS
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：US20150011541A1

  公开（公告）日：2015-01-08

  The present invention relates to compounds having a pipecolate sulfonamide scaffold, pharmaceutically acceptable salts of these compounds and pharmaceutical compositions containing at least one of these compounds together with pharmaceutically acceptable carrier, excipient and/or diluents. Said pipecolate sulfonamide compounds can be used for prophylaxis and/or treatment of psychiatric disorders and neurodegenerative diseases, disorders and conditions.

  本发明涉及具有pipecolate磺酰胺支架的化合物，这些化合物的药学可接受盐以及含有至少一种这些化合物和药学可接受的载体、赋形剂和/或稀释剂的制药组合物。所述pipecolate磺酰胺化合物可用于预防和/或治疗精神障碍和神经退行性疾病、疾病和病况。
• Pipecolic Acid Derivatives As Small-Molecule Inhibitors of the <i>Legionella</i> MIP Protein
  作者：Christina Juli、Martin Sippel、Jens Jäger、Alexandra Thiele、Matthias Weiwad、Kristian Schweimer、Paul Rösch、Michael Steinert、Christoph A. Sotriffer、Ulrike Holzgrabe

  DOI：10.1021/jm101156y

  日期：2011.1.13

  The macrophage infectivity potentiator (MIP) protein is a major virulence factor of Legionella pneumophila, the causative agent of Legionnaires' disease MIP belongs to the FK506-binding proteins (FKBP) and is necessary for optimal intracellular survival and lung tissue dissemination of L pneumophila We aimed to identify new small-molecule inhibitors of MIP by starting from known FKBP12 ligands Computational analysis, synthesis, and biological testing of pipecolic acid derivatives revealed a promising scaffold for new MIP inhibitors
• Development, synthesis and structure–activity-relationships of inhibitors of the macrophage infectivity potentiator (Mip) proteins of Legionella pneumophila and Burkholderia pseudomallei
  作者：Florian Seufert、Maximilian Kuhn、Michael Hein、Matthias Weiwad、Mirella Vivoli、Isobel H. Norville、Mitali Sarkar-Tyson、Laura E. Marshall、Kristian Schweimer、Heike Bruhn、Paul Rösch、Nicholas J. Harmer、Christoph A. Sotriffer、Ulrike Holzgrabe

  DOI：10.1016/j.bmc.2016.08.025

  日期：2016.11

  The bacteria Burkholderia pseudomallei and Legionella pneumophila cause severe diseases like melioidosis and Legionnaire's disease with high mortality rates despite antibiotic treatment. Due to increasing antibiotic resistances against these and other Gram-negative bacteria, alternative therapeutical strategies are in urgent demand. As a virulence factor, the macrophage infectivity potentiator (Mip) protein constitutes an attractive target. The Mip proteins of B. pseudomallei and L. pneumophila exhibit peptidyl-prolyl cis/trans isomerase (PPIase) activity and belong to the PPIase superfamily. In previous studies, the pipecolic acid moiety proved to be a valuable scaffold for inhibiting this PPIase activity. Thus, a library of pipecolic acid derivatives was established guided by structural information and computational analyses of the binding site and possible binding modes. Stability and toxicity considerations were taken into account in iterative extensions of the library. Synthesis and evaluation of the compounds in PPlase assays resulted in highly active inhibitors. The activities can be interpreted in terms of a common binding mode obtained by docking calculations. (C) 2016 Elsevier Ltd. All rights reserved.