methyl 8-amino-7-chloro-2,3-dihydro-benzo[1,4]dioxine-5-carboxylate | 1428863-09-5

• 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: methyl 8-amino-7-chloro-2,3-dihydro-benzo[1,4]dioxine-5-carboxylate
• 英文别名: methyl 8-amino-7-chloro-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylate；methyl 8-amino-7-chloro-2,3-dihydrobenzo[1,4]dioxane-5-carboxylate；Methyl 5-amino-6-chloro-2,3-dihydro-1,4-benzodioxine-8-carboxylate
• CAS: 1428863-09-5
• 化学式: C₁₀H₁₀ClNO₄
• 分子量: 243.647
• InChiKey: ONJDRVXASMJJAT-UHFFFAOYSA-N

物化性质

• 沸点：
  417.4±45.0 °C(Predicted)
• 密度：
  1.429±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  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 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.83h， 生成 (1-(2-[¹⁸F]fluoroethyl)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
• 作为产物：
  描述：

  甲基8-氨基-2,3-二氢-1,4-苯并二氧杂环己烷-5-羧酸酯 在 N-氯代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以85%的产率得到methyl 8-amino-7-chloro-2,3-dihydro-benzo[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

• HETEROARYL COMPOUNDS AS 5-HT4 RECEPTOR LIGANDS
  申请人：SUVEN LIFE SCIENCES LIMITED

  公开号：US20140187581A1

  公开（公告）日：2014-07-03

  The present invention relates to novel compounds of formula (I), and their pharmaceutically acceptable salts and compositions containing them. The present invention also relates to a process for the preparation of above said novel compounds, and their pharmaceutically acceptable salts. The compounds of formula (I) are useful in the treatment of various disorders that are related to 5-HT 4 receptors.

  本发明涉及式(I)的新化合物，以及它们的药用盐和含有它们的组合物。 本发明还涉及制备上述新化合物的方法，以及它们的药用盐。式(I)的化合物在治疗与5-HT 4 受体相关的各种疾病中是有用的。
• [EN] HETEROARYL COMPOUNDS AS 5-HT4 RECEPTOR LIGANDS<br/>[FR] COMPOSÉS HÉTÉROARYLES CONVENANT COMME LIGANDS DU RÉCEPTEUR 5-HT4
  申请人：SUVEN LIFE SCIENCES LTD

  公开号：WO2013042135A8

  公开（公告）日：2013-08-15
• US9079894B2
  申请人：——

  公开号：US9079894B2

  公开（公告）日：2015-07-14
• US9636335B2
  申请人：——

  公开号：US9636335B2

  公开（公告）日：2017-05-02