(1-(3-fluoropropyl)piperidin-4-yl)methyl 8-amino-7-chloro-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylate

• 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: (1-(3-fluoropropyl)piperidin-4-yl)methyl 8-amino-7-chloro-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylate
• 英文别名: [1-(3-Fluoropropyl)piperidin-4-yl]methyl 5-amino-6-chloro-2,3-dihydro-1,4-benzodioxine-8-carboxylate；[1-(3-fluoropropyl)piperidin-4-yl]methyl 5-amino-6-chloro-2,3-dihydro-1,4-benzodioxine-8-carboxylate
• 化学式: C₁₈H₂₄ClFN₂O₄
• 分子量: 386.851
• InChiKey: AITVFSBTANYJCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  74
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 8-amino-7-chloro-2,3-dihydro-benzo[1,4]dioxine-5-carboxylate 在 正丁基锂 、 caesium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 7.33h， 生成 (1-(3-fluoropropyl)piperidin-4-yl)methyl 8-amino-7-chloro-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of positron emission tomography radiotracers targeting serotonin 4 receptors in brain: [18F]MNI-698 and [18F]MNI-699

  摘要：

  Two new benzodioxane derivatives were synthesized as candidates to image the serotonin 4 receptors by positron emission tomography (PET) and radiolabeled with fluorine-18 via a two-step procedure. Competition binding assays demonstrated that MNI-698 and MNI-699 had sub-nanomolar binding affinities against rat striatal 5-HT4 receptors (Ki of 0.20 and 0.07 nM, respectively). PET imaging in rhesus monkey showed that the regional brain distribution of [F-18] MNI-698 and [F-18] MNI-699 were consistent with the known densities of 5-HT4 in brain. [F-18] MNI-698 and [F-18] MNI-699 are among the first fluorine-18 radiotracers developed for imaging the 5-HT4 receptors in vivo and are currently under preclinical investigation in primates for future human use. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.097

文献信息

• Synthesis and biological evaluation of positron emission tomography radiotracers targeting serotonin 4 receptors in brain: [18F]MNI-698 and [18F]MNI-699
  作者：Fabien Caillé、Thomas J. Morley、Adriana Alexandre S. Tavares、Caroline Papin、Nicole M. Twardy、David Alagille、H. Sharon Lee、Ronald M. Baldwin、John P. Seibyl、Olivier Barret、Gilles D. Tamagnan

  DOI：10.1016/j.bmcl.2013.09.097

  日期：2013.12

  Two new benzodioxane derivatives were synthesized as candidates to image the serotonin 4 receptors by positron emission tomography (PET) and radiolabeled with fluorine-18 via a two-step procedure. Competition binding assays demonstrated that MNI-698 and MNI-699 had sub-nanomolar binding affinities against rat striatal 5-HT4 receptors (Ki of 0.20 and 0.07 nM, respectively). PET imaging in rhesus monkey showed that the regional brain distribution of [F-18] MNI-698 and [F-18] MNI-699 were consistent with the known densities of 5-HT4 in brain. [F-18] MNI-698 and [F-18] MNI-699 are among the first fluorine-18 radiotracers developed for imaging the 5-HT4 receptors in vivo and are currently under preclinical investigation in primates for future human use. (C) 2013 Elsevier Ltd. All rights reserved.