4-amino-5-iodo-N-[[1-(cyclohexylmethyl)-4-piperidyl]methyl]-2-methoxybenzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-amino-5-iodo-N-[[1-(cyclohexylmethyl)-4-piperidyl]methyl]-2-methoxybenzamide
• 英文别名: 4-amino-N-{[1-(cyclohexylmethyl)-4-piperidyl]methyl}-5-iodo-2-methoxybenzamide；4-amino-N-[[1-(cyclohexylmethyl)piperidin-4-yl]methyl]-5-iodo-2-methoxybenzamide
• 化学式: C₂₁H₃₂IN₃O₂
• 分子量: 485.408
• InChiKey: OINBXQVAEUFUNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  67.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  哌啶-4-甲酰胺 在 lithium aluminium tetrahydride 、 双氧水 、 potassium carbonate 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 78.0h， 生成 4-amino-5-iodo-N-[[1-(cyclohexylmethyl)-4-piperidyl]methyl]-2-methoxybenzamide
  参考文献：
  名称：

  Synthesis and evaluation of novel serotonin 4 receptor radiotracers for single photon emission computed tomography

  摘要：

  Despite its implication in several physiological and pathological processes the serotonin subtype-4 receptor (5-HT4R) has seen limited effort for the development of radiolabeling agent especially concerning single photon emission computed tomography (SPECT). Bearing an ester function, the available ligands are rapidly susceptible to hydrolysis which limits their use in vivo. In this study the synthesis of iodinated benzamide and ketone analogs were described. Their affinity for the 5-HT4R and their lipophilicity were evaluated and the most promising derivatives were evaluated ex vivo for their binding to the receptor and for their ability to displace the reference ligand [I-125]-SB207710. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.059

文献信息

• ACETYLCHOLINESTERASE INHIBITOR COMPOUNDS AND 5HT4 SEROTONERGIC RECEPTOR AGONISTS, WITH PROMNSIA EFFECT, METHODS FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
  申请人：UNIVERSITE DE CAEN

  公开号：US20160122300A1

  公开（公告）日：2016-05-05

  Compounds are provided according to Formula (I) as well as their enantiomers and their racemics, their acid salts, their hydrates or their solvation products. Among a large number of possible meanings, X represents a halogen, Y an oxygen atom; all of the coefficients m, n, r and s have the value 1, R represents an ethyl and R′ a cycloalkyl. The invention also includes Methods of preparing the above compounds and the pharmaceutical compositions containing them also are provided.

  化合物根据公式（I）提供，以及它们的对映体和它们的混合物，它们的酸盐，它们的水合物或它们的溶剂化物。在许多可能的含义中，X代表卤素，Y代表氧原子；所有系数m，n，r和s的值均为1，R代表乙基，R′代表环烷基。该发明还包括制备上述化合物的方法以及含有它们的制药组合物。
• COMPOSES INHIBITEURS DE L'ACETYLCHOLINESTERASE ET AGONISTES DES RECEPTEURS SEROTONINERGIQUES 5HT4, A EFFET PROMNESIANT, LEURS PROCEDES DE PREPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：Université de Caen

  公开号：EP3004058B1

  公开（公告）日：2020-06-10
• US9663465B2
  申请人：——

  公开号：US9663465B2

  公开（公告）日：2017-05-30
• Synthesis and evaluation of novel serotonin 4 receptor radiotracers for single photon emission computed tomography
  作者：Julien Lalut、Benjamin B. Tournier、Thomas Cailly、Cédric Lecoutey、Sophie Corvaisier、Audrey Davis、Céline Ballandonne、Marc Since、Philippe Millet、Frédéric Fabis、Patrick Dallemagne、Christophe Rochais

  DOI：10.1016/j.ejmech.2016.03.059

  日期：2016.6

  Despite its implication in several physiological and pathological processes the serotonin subtype-4 receptor (5-HT4R) has seen limited effort for the development of radiolabeling agent especially concerning single photon emission computed tomography (SPECT). Bearing an ester function, the available ligands are rapidly susceptible to hydrolysis which limits their use in vivo. In this study the synthesis of iodinated benzamide and ketone analogs were described. Their affinity for the 5-HT4R and their lipophilicity were evaluated and the most promising derivatives were evaluated ex vivo for their binding to the receptor and for their ability to displace the reference ligand [I-125]-SB207710. (C) 2016 Elsevier Masson SAS. All rights reserved.