tert-butyl (2R)-2-[2-(4-methylpiperidin-1-yl)-2-oxoethyl]pyrrolidine-1-carboxylate | 1314696-16-6

• 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: tert-butyl (2R)-2-[2-(4-methylpiperidin-1-yl)-2-oxoethyl]pyrrolidine-1-carboxylate
• CAS: 1314696-16-6
• 化学式: C₁₇H₃₀N₂O₃
• 分子量: 310.437
• InChiKey: HSSDTYRFYYTVCP-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R)-2-[2-(4-methylpiperidin-1-yl)-2-oxoethyl]pyrrolidine-1-carboxylate 在 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (R)-2-[2-(4-methyl-piperidin-1-yl)ethyl]pyrrolidine
  参考文献：
  名称：

  Synthesis and biological evaluation of potential 5-HT7 receptor PET radiotracers

  摘要：

  Brain serotonin 7 receptor (5-HT7) is involved in several mood disorders and drug candidates targeting this subtype are currently in development. Positron emission tomography (PET) is a molecular imaging modality offering great promise for accelerating the process from preclinical discovery to clinical phases. As no PET radiopharmaceutical has yet been used successfully to study the 5-HT7 receptor in vivo, our objective is to develop the first 5-HT7 fluorine-18 labeled radiotracer.Four structural analogs of SB269970, a specific 5-HT7 receptor antagonist, divided in FP3 series and FPMP series were synthesized. Their antagonist effects were investigated by cellular functional assay. Nitro-precursors of these analogs were radiolabeled via a [F-18(-)]nucleophilic substitution and in vitro autoradiographies were performed in rat brain.Chemical and radiochemical purities of fluorine radiotracers were >99% with specific activities in 40 -129 GBq/mu mole range. The four derivates presented antagonism potencies toward 5-HT7 receptors (PKB) between 7.8 and 8.8. The four PET radiotracers had suitable characteristic for 5-HT7 receptor probing in vitro even if the FP3 series seemed to be more specific for this receptor. These results encourage us to pursue in vivo studies. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.010
• 作为产物：
  描述：

  (R)-吡咯烷-2-乙酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl (2R)-2-[2-(4-methylpiperidin-1-yl)-2-oxoethyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of potential 5-HT7 receptor PET radiotracers

  摘要：

  Brain serotonin 7 receptor (5-HT7) is involved in several mood disorders and drug candidates targeting this subtype are currently in development. Positron emission tomography (PET) is a molecular imaging modality offering great promise for accelerating the process from preclinical discovery to clinical phases. As no PET radiopharmaceutical has yet been used successfully to study the 5-HT7 receptor in vivo, our objective is to develop the first 5-HT7 fluorine-18 labeled radiotracer.Four structural analogs of SB269970, a specific 5-HT7 receptor antagonist, divided in FP3 series and FPMP series were synthesized. Their antagonist effects were investigated by cellular functional assay. Nitro-precursors of these analogs were radiolabeled via a [F-18(-)]nucleophilic substitution and in vitro autoradiographies were performed in rat brain.Chemical and radiochemical purities of fluorine radiotracers were >99% with specific activities in 40 -129 GBq/mu mole range. The four derivates presented antagonism potencies toward 5-HT7 receptors (PKB) between 7.8 and 8.8. The four PET radiotracers had suitable characteristic for 5-HT7 receptor probing in vitro even if the FP3 series seemed to be more specific for this receptor. These results encourage us to pursue in vivo studies. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.010

文献信息

• Synthesis and biological evaluation of potential 5-HT7 receptor PET radiotracers
  作者：Julien Andries、Laetitia Lemoine、Didier Le Bars、Luc Zimmer、Thierry Billard

  DOI：10.1016/j.ejmech.2011.05.010

  日期：2011.8

  Brain serotonin 7 receptor (5-HT7) is involved in several mood disorders and drug candidates targeting this subtype are currently in development. Positron emission tomography (PET) is a molecular imaging modality offering great promise for accelerating the process from preclinical discovery to clinical phases. As no PET radiopharmaceutical has yet been used successfully to study the 5-HT7 receptor in vivo, our objective is to develop the first 5-HT7 fluorine-18 labeled radiotracer.Four structural analogs of SB269970, a specific 5-HT7 receptor antagonist, divided in FP3 series and FPMP series were synthesized. Their antagonist effects were investigated by cellular functional assay. Nitro-precursors of these analogs were radiolabeled via a [F-18(-)]nucleophilic substitution and in vitro autoradiographies were performed in rat brain.Chemical and radiochemical purities of fluorine radiotracers were >99% with specific activities in 40 -129 GBq/mu mole range. The four derivates presented antagonism potencies toward 5-HT7 receptors (PKB) between 7.8 and 8.8. The four PET radiotracers had suitable characteristic for 5-HT7 receptor probing in vitro even if the FP3 series seemed to be more specific for this receptor. These results encourage us to pursue in vivo studies. (C) 2011 Elsevier Masson SAS. All rights reserved.