4-(2-methylphenyl)piperidine-2,6-dione | 885982-06-9

• 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: 4-(2-methylphenyl)piperidine-2,6-dione
• CAS: 885982-06-9
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: KITIERMCDRQZNR-UHFFFAOYSA-N

物化性质

• 沸点：
  406.2±34.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-methylphenyl)piperidine-2,6-dione 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以81%的产率得到4-(2-甲苯基)哌啶
  参考文献：
  名称：

  Synthesis and binding affinities of methylvesamicol analogs for the acetylcholine transporter and sigma receptor

  摘要：

  We synthesized methylvesamicol analogs 13-16 and investigated the binding characteristics of 2-[4-phenylpiperidino]cyclohexanol (vesamicol) and methylvesamicol analogs 13-16, with a methyl group introduced into the 4-phenylpiperidine moiety, to sigma receptors (sigma-1, sigma-2) and to vesicular acetylcholine transporters (VAChT) in membranes of the rat brain and liver. In competitive inhibition studies, (-)-o-methylvesamicol [(-)-OMV] (13) (K-i = 6.7 nM), as well as (-)-vesamicol (K-i = 4.4 nM), had a high affinity for VAChT. (+)-p-Methylvesamicol [(+)-PMV] (16) (K-i = 3.0 nM), as well as SA4503 (K-i = 4.4 nM), reported as a sigma-1 mapping agent for positron emission tomography (PET), had a high affinity for the sigma-1 receptor. The binding affinity of (+)-PMV (1-16) for the sigma-1 receptor (K-i = 3.0 nM) was about 13 times higher than that for the sigma-2 (sigma-2) receptor (K-i = 40.7 nM). (+)-PMV (16) (K-i = 199 nM) had a much lower affinity for VAChT than SA4503 (K-i = 50.2 nM) and haloperidol (K-i = 41.4 nM). These results showed that the binding characteristics of (-)-OMV (13) to VAChT were similar to those of (-)-vesamicol and that (+)-PMV (16) bound to the sigma-1 receptor with high affinity. In conclusion, (-)-OMV (13) and (+)-PMV (16). which had a Suitable structure, with a methyl group for labeling with C-11, may become not only a new VAChT ligand and a new type of sigma receptor ligand, respectively, but may also become a new target compound of VAChT and the sigma-1 receptor radioligand for PET, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.044
• 作为产物：
  描述：

  2-溴苯甲醛乙烯醛 在 四氢吡咯 、 盐酸 、 氯化亚砜 、 sodium ethanolate 、 sodium hydride 、 magnesium 、 溶剂黄146 、 丙酮 、 尿素 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 114.08h， 生成 4-(2-methylphenyl)piperidine-2,6-dione
  参考文献：
  名称：

  Synthesis and binding affinities of methylvesamicol analogs for the acetylcholine transporter and sigma receptor

  摘要：

  We synthesized methylvesamicol analogs 13-16 and investigated the binding characteristics of 2-[4-phenylpiperidino]cyclohexanol (vesamicol) and methylvesamicol analogs 13-16, with a methyl group introduced into the 4-phenylpiperidine moiety, to sigma receptors (sigma-1, sigma-2) and to vesicular acetylcholine transporters (VAChT) in membranes of the rat brain and liver. In competitive inhibition studies, (-)-o-methylvesamicol [(-)-OMV] (13) (K-i = 6.7 nM), as well as (-)-vesamicol (K-i = 4.4 nM), had a high affinity for VAChT. (+)-p-Methylvesamicol [(+)-PMV] (16) (K-i = 3.0 nM), as well as SA4503 (K-i = 4.4 nM), reported as a sigma-1 mapping agent for positron emission tomography (PET), had a high affinity for the sigma-1 receptor. The binding affinity of (+)-PMV (1-16) for the sigma-1 receptor (K-i = 3.0 nM) was about 13 times higher than that for the sigma-2 (sigma-2) receptor (K-i = 40.7 nM). (+)-PMV (16) (K-i = 199 nM) had a much lower affinity for VAChT than SA4503 (K-i = 50.2 nM) and haloperidol (K-i = 41.4 nM). These results showed that the binding characteristics of (-)-OMV (13) to VAChT were similar to those of (-)-vesamicol and that (+)-PMV (16) bound to the sigma-1 receptor with high affinity. In conclusion, (-)-OMV (13) and (+)-PMV (16). which had a Suitable structure, with a methyl group for labeling with C-11, may become not only a new VAChT ligand and a new type of sigma receptor ligand, respectively, but may also become a new target compound of VAChT and the sigma-1 receptor radioligand for PET, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.044

文献信息

• Ligand for Vesicular Acetylcholine Transporter
  申请人：Shiba Kazuhiro

  公开号：US20090163461A1

  公开（公告）日：2009-06-25

  The present invention provides a novel compound represented by the formula (I): wherein R 1 and R 2 are as defined in the specification, or a salt thereof, which is useful as a reagent (radiotracer) for VAChT mapping and the like, and can be used for positron emission tomography (PET), and a production method of the compound. Moreover, the present invention provides a diagnostic reagent for diagnosing cholinergic neurodegenerative disorders (e.g., Alzheimer's disease, memory disorder, learning disorder, schizophrenia, cognitive dysfunction, hyperactivity disorder, anxiety neurosis, depression, analgia, Parkinson's disease and the like) and the like, which contains the aforementioned compound.

  本发明提供了一种新的化合物，其化学式为（I），其中R1和R2如规范中定义，或其盐，该化合物可用作VAChT映射等试剂（放射性示踪剂），可用于正电子发射断层扫描（PET），以及该化合物的制备方法。此外，本发明还提供了一种诊断试剂，用于诊断胆碱能神经退行性疾病（例如，阿尔茨海默病、记忆障碍、学习障碍、精神分裂症、认知功能障碍、多动症、焦虑神经症、抑郁症、无痛觉症、帕金森病等），其中包含上述化合物。
• Catalytic Enantioselective Desymmetrization of Prochiral Triacylamines via Pseudopeptidic Guanidine–Guanidinium Catalysis
  作者：Hu Qu、Xin-Shen Liang、Wen-Juan Wang、Xian-He Zhao、Yu-Hua Deng、Xian-Tao An、Wen-Dao Chu、Xiang-Zhi Zhang、Chun-An Fan

  DOI：10.1021/acs.orglett.2c02785

  日期：2022.9.23

  Triacylamines with Cs symmetry have been explored in asymmetric organocatalysis, leading to the development of a novel catalytic enantioselective desymmetrization of prochiral triacylamines by methanolysis under the catalysis of chiral pseudopeptidic guanidine–guanidinium salt having a weakly coordinating anion. This organocatalytic methodology provides an effective approach to the synthetically useful

  已经在不对称有机催化中探索了具有C s对称性的三酰基胺，从而在具有弱配位阴离子的手性假肽胍-胍盐的催化下通过甲醇分解开发了一种新的催化对映选择性去对称化前手性三酰基胺。这种有机催化方法为合成有用的具有 1,5-二羰基部分的手性酰亚胺酯提供了一种有效的方法，其合成潜力已在两种 GABA 类似药物的不对称合成中得到体现，( R )-巴氯芬·HCl 和 ( S )-普瑞巴林。
• LIGAND FOR VESICULAR ACETYLCHOLINE TRANSPORTER
  申请人：National University Corporation Kanazawa University

  公开号：EP1867634B1

  公开（公告）日：2010-05-26
• Synthesis and binding affinities of methylvesamicol analogs for the acetylcholine transporter and sigma receptor
  作者：Kazuhiro Shiba、Kazuma Ogawa、Kiichi Ishiwata、Kazuyoshi Yajima、Hirofumi Mori

  DOI：10.1016/j.bmc.2005.11.044

  日期：2006.4

  We synthesized methylvesamicol analogs 13-16 and investigated the binding characteristics of 2-[4-phenylpiperidino]cyclohexanol (vesamicol) and methylvesamicol analogs 13-16, with a methyl group introduced into the 4-phenylpiperidine moiety, to sigma receptors (sigma-1, sigma-2) and to vesicular acetylcholine transporters (VAChT) in membranes of the rat brain and liver. In competitive inhibition studies, (-)-o-methylvesamicol [(-)-OMV] (13) (K-i = 6.7 nM), as well as (-)-vesamicol (K-i = 4.4 nM), had a high affinity for VAChT. (+)-p-Methylvesamicol [(+)-PMV] (16) (K-i = 3.0 nM), as well as SA4503 (K-i = 4.4 nM), reported as a sigma-1 mapping agent for positron emission tomography (PET), had a high affinity for the sigma-1 receptor. The binding affinity of (+)-PMV (1-16) for the sigma-1 receptor (K-i = 3.0 nM) was about 13 times higher than that for the sigma-2 (sigma-2) receptor (K-i = 40.7 nM). (+)-PMV (16) (K-i = 199 nM) had a much lower affinity for VAChT than SA4503 (K-i = 50.2 nM) and haloperidol (K-i = 41.4 nM). These results showed that the binding characteristics of (-)-OMV (13) to VAChT were similar to those of (-)-vesamicol and that (+)-PMV (16) bound to the sigma-1 receptor with high affinity. In conclusion, (-)-OMV (13) and (+)-PMV (16). which had a Suitable structure, with a methyl group for labeling with C-11, may become not only a new VAChT ligand and a new type of sigma receptor ligand, respectively, but may also become a new target compound of VAChT and the sigma-1 receptor radioligand for PET, respectively. (c) 2005 Elsevier Ltd. All rights reserved.