4-Iodobenzetimide | 119391-56-9

• 物质功能分类: 生物化工 - 生化试剂 - 激动剂抑制剂
• 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-Iodobenzetimide
• 英文别名: mAChR-IN-1；3-[1-[(4-iodophenyl)methyl]piperidin-4-yl]-3-phenylpiperidine-2,6-dione
• CAS: 119391-56-9
• 化学式: C₂₃H₂₅IN₂O₂
• 分子量: 488.368
• InChiKey: WJLRTFJPHDSXAF-UHFFFAOYSA-N

物化性质

• 溶解度：
  二甲基亚砜：≥ 52 mg/mL（106.48 mM）

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

制备方法与用途

生物活性方面，mAChR-IN-1是一种高效的mAChR抑制剂，其IC50值为17 nM。

反应信息

• 作为产物：
  描述：

  3-苯基-1'-(苯基甲基)-[3,4'-联哌啶]-2,6-二酮 在 palladium on activated charcoal 盐酸 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 72.0h， 生成 4-Iodobenzetimide
  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

文献信息

• [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.
• Synthesis and biological evaluation of iodine-125- and iodine-123-4-iododexetimide, a potent muscarinic cholinergic receptor antagonist
  作者：Alan A. Wilson、Robert F. Dannals、Hayden T. Ravert、J. James Frost、Henry N. Wagner

  DOI：10.1021/jm00125a021

  日期：1989.5

  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.