N-[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]benzothio-phene-5-carboxamide | 1617538-55-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: N-[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]benzothio-phene-5-carboxamide
• CAS: 1617538-55-2
• 化学式: C₁₇H₂₀N₂OS
• 分子量: 300.425
• InChiKey: YDNFGBHSAUTPQD-QDMKHBRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  32.34
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-苯并噻吩-5-羧酸 、 3-endo-tropanamine hydrochloride 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以80%的产率得到N-[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]benzothio-phene-5-carboxamide
  参考文献：
  名称：

  Design of α7 nicotinic acetylcholine receptor ligands in quinuclidine, tropane and quinazoline series. Chemistry, molecular modeling, radiochemistry, in vitro and in rats evaluations of a [18F] quinuclidine derivative

  摘要：

  In this report, we describe the synthesis of a novel library of alpha 7 nAChR ligands based on the modulation of the quinuclidine, quinazoline and tropane moieties. Spirane derivatives were newly synthesized under stereo specific 1,3 dipolar cylcoadditions. Only amide derivatives bonded efficiently to the receptor with Ki measured between 14 and 133 nM. The best fluorinated candidate was selected and radiolabeled. The potent [F-18]4 PET tracer was evaluated in rats and its brain accumulation quantified. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.057

文献信息

• Design of α7 nicotinic acetylcholine receptor ligands in quinuclidine, tropane and quinazoline series. Chemistry, molecular modeling, radiochemistry, in vitro and in rats evaluations of a [18F] quinuclidine derivative
  作者：Frédéric Pin、Johnny Vercouillie、Aziz Ouach、Sylvie Mavel、Zuhal Gulhan、Gabrielle Chicheri、Christian Jarry、Stephane Massip、Jean-Bernard Deloye、Denis Guilloteau、Franck Suzenet、Sylvie Chalon、Sylvain Routier

  DOI：10.1016/j.ejmech.2014.04.057

  日期：2014.7

  In this report, we describe the synthesis of a novel library of alpha 7 nAChR ligands based on the modulation of the quinuclidine, quinazoline and tropane moieties. Spirane derivatives were newly synthesized under stereo specific 1,3 dipolar cylcoadditions. Only amide derivatives bonded efficiently to the receptor with Ki measured between 14 and 133 nM. The best fluorinated candidate was selected and radiolabeled. The potent [F-18]4 PET tracer was evaluated in rats and its brain accumulation quantified. (C) 2014 Elsevier Masson SAS. All rights reserved.