3-苯基-[3,4-联哌啶]-2,6-二酮 | 19315-71-0

• 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
• 中文名称: 3-苯基-[3,4-联哌啶]-2,6-二酮
• 英文名称: Norbenzylbenzetimide
• 英文别名: 4-(3-Phenyl-2,6-dioxo-3-piperidyl)-piperidin；3-phenyl-octahydro-[3,4']bipyridinyl-2,6-dione；3-phenyl-[3,4'-bipiperidine]-2,6-dione；Nor-benzetimide；3-phenyl-3-piperidin-4-ylpiperidine-2,6-dione
• CAS: 19315-71-0
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: WCKABEIXAFZEIO-UHFFFAOYSA-N

物化性质

• 沸点：
  476.5±45.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  3

制备方法与用途

生物活性方面，Nor-benzetimide 是 Benzetimide 的主要代谢产物。Benzetimide 本身是一种具有抗胆碱能活性的mAChR拮抗剂。

反应信息

• 作为反应物：
  描述：

  3-苯基-[3,4-联哌啶]-2,6-二酮 、 3-氯苄溴 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 1'-(3-chloro-benzyl)-3-phenyl-octahydro-[3,4']bipyridinyl-2,6-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of iodine-125- and iodine-123-4-iododexetimide, a potent muscarinic cholinergic receptor antagonist

  摘要：

  A series of halogenated racemic analogues of dexetimide (1) was synthesized and their affinity for the muscarinic cholinergic receptor measured. One analogue, 4-iododexetimide (21), was efficiently labeled with 125I and 123I at high specific activity. In vitro binding studies and in vivo biodistribution studies suggest that 123I-labeled 21 may be useful for imaging muscarinic cholinergic receptors in the living human brain with single photon emission computed tomography.

  DOI：

  10.1021/jm00125a021
• 作为产物：
  描述：

  4-Bromobenzetimide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 3-苯基-[3,4-联哌啶]-2,6-二酮
  参考文献：
  名称：

  Synthesis and structure–activity relationship of benzetimide derivatives as human CXCR3 antagonists

  摘要：

  The synthesis and evaluation of benzetimide derivatives showing potent CXCR3 antagonism are described. Optimization of the screening hits led to the identification of more potent CXCR3 antagonists devoid of anti-cholinergic activity and identification of the key pharmacophore moieties of the series. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.115

文献信息

• WO2007/90826
  申请人：——

  公开号：——

  公开（公告）日：——
• WILSON, ALAN A.;DANNALS, ROBERT F.;RAVERT, HAYDEN T.;FROST, J. JAMES;WAGN+, J. MED. CHEM., 32,(1989) N, C. 1057-1062
  作者：WILSON, ALAN A.、DANNALS, ROBERT F.、RAVERT, HAYDEN T.、FROST, J. JAMES、WAGN+

  DOI：——

  日期：——
• PIPERIDINE DERIVATIVES AS CXCR3 RECEPTOR ANTAGONISTS
  申请人：Janssen Pharmaceutica, N.V.

  公开号：EP1984349A1

  公开（公告）日：2008-10-29
• Piperidine Derivatives as Cxcr3 Receptor Antagonists
  申请人：Coesemans Erwin

  公开号：US20090030039A1

  公开（公告）日：2009-01-29

  The present invention relates to a compound of formula (I) a N-oxide thereof, a pharmaceutically acceptable salt thereof, a stereochemically isomeric form thereof or a solvate thereof, wherein X represents N or CH; Y and Z each independently represent C(═O) or CH 2 provided that at least one of Y and Z represents C(═O); R 1 represents CH(R 4 )-aryl or CH(R 4 )-heteroaryl; R 2 represents aryl 2 or heteroaryl; R 3 represents hydrogen; C 1-4 alkylcarbonyl; C 1-6 alkyl optionally substituted with C 1-6 alkyloxy, C 1-6 alkylthio, C 1-6 alkyloxycarbonyl or aryl 1 ; provided that when Y and Z each represent C(═O), X represents CH, R 3 represents hydrogen, R 4 represents hydrogen, and R 2 represents unsubstituted pyridyl or phenyl optionally substituted with one halo or with one C 1-4 alkyloxy or with one or two C 1-4 alkyl, then aryl in the definition of R 1 is other than phenyl substituted with one halo or with one or two C 1-4 alkyl; and provided that when Y and Z each represent C(═O), X represents CH, R 3 represents hydrogen, and R 2 represents unsubstituted pyridyl or phenyl optionally substituted with one halo or with one C 1-4 alkyloxy or with one or two C 1-4 alkyl, then heteroaryl in the definition of R 1 is other than unsubstituted thienyl or unsubstituted pyridyl. The present invention also relates to the use of a compound of formula (I) for the manufacture of a medicament for preventing or treating a disease mediated through activation of the CXCR3 receptor; to processes for preparing the compounds of formula (I) and pharmaceutical compositions comprising them.
• [EN] RADIOLABELLED LIGANDS FOR MUSCARINIC RECEPTORS<br/>[FR] LIGANDS RADIOMARQUES POUR RECEPTEURS MUSCARINIQUES
  申请人：AUSTRALIAN NUCLEAR SCIENCE & TECHNOLOGY ORGANISATION

  公开号：WO1995011234A1

  公开（公告）日：1995-04-27

  (EN) Compounds of formula (I), radiolabelled compounds or pharmaceutically acceptable salts thereof where X- is a suitable counter ion; R1 is H; alkyl, alkenyl, alkynyl, phenyl or phenylalkyl each optionally substituted; R2 is one or more selected from hydrogen, halogen, radioactive isotopes of halogen, OR, CN, CF3, NO2, COOR, NRR', SR, COR, CONRR', SO3R, SO2NRR', SOR and SO2R where R and R' are independently selected from H, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl or optionally substituted phenylalkyl; wherein the optional substituents are one or more selected from alkyl, alkenyl, alkynyl, phenyl, halogen, radioactive isotopes of halogen, OR, CN, CF3, NO2, COOR, NRR', SR, COR, CONRR', SO3R, SO2NRR', SOR and SO2R where R and R' are as defined above suitable for imaging muscarinic receptors of the heart.(FR) L'invention concerne des composés de la formule (I), des composés radiomarqués ou des sels de ceux-ci acceptables pharmaceutiquement, formule dans laquelle X- représente un contre-ion approprié; R1 représente H; alkyle, alcényle, alcynyle, phényle ou phénylalkyle étant chacun facultativement substitué; R2 représente un ou plusieurs éléments choisi(s) parmi hydrogène, halogène, des isotopes radioactifs d'halogène, OR, CN, CF3, NO2, COOR, NRR', SR, COR, CONRR', SO3R, SO2NRR', SOR et SO2R, dans lesquels R et R' sont choisis indépendamment parmi H, alkyle facultativement substitué, alcényle facultativement substitué, alcynyle facultativement substitué, phényle ou phénylalkyle facultativement substitués; et dans laquelle les substituants facultatifs sont un ou plusieurs éléments choisi(s) parmi alkyle, alcényle, alcynyle, phényle, halogène, des isotopes radioactifs d'halogène, OR, CN, CF3, NO2, COOR, NRR', SR, COR, CONRR', SO3R, SO2NRR', SOR et SO2R, dans lesquels R et R' sont tels que définis ci-dessus. Ces composés permettent la visualisation des récepteurs muscariniques du coeur.