(+/-)-4-Oxo-thiochroman-2-carboxylic acid diethyl amide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫铬烷
• 英文名称: (+/-)-4-Oxo-thiochroman-2-carboxylic acid diethyl amide
• 英文别名: N,N-diethyl-4-oxothiochroman-2-carboxamide；N,N-diethyl-4-oxo-2,3-dihydrothiochromene-2-carboxamide
• 化学式: C₁₄H₁₇NO₂S
• 分子量: 263.36
• InChiKey: AJPFIIAMHFPSJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-4-Oxo-thiochroman-2-carboxylic acid diethyl amide 在 吡啶 、 硫酸 、 四丁基氟化铵 、 sodium hydride 、 potassium hydrogencarbonate 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 、 氢氟酸 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.17h， 生成 11-(2-(18)F-fluoroethyl)-7-methoxy-6,11-dihydro-5-thia-11-aza-benzo[a]fluorene-6-carboxylic acid diethylamide
  参考文献：
  名称：

  Exploration of the structure–activity relationship of a novel tetracyclic class of TSPO ligands—Potential novel positron emitting tomography imaging agents

  摘要：

  A series of novel TSPO ligands based on the tetracyclic class of translocator protein (TSPO) ligands first described by Okubo et al. was synthesised and evaluated as potential positron emitting tomography (PET) ligands for imaging TPSO in vivo. Fluorine-18 labelling of the molecules was achieved using direct radiolabelling or synthon based labelling approaches. Several of the ligands prepared have promising profiles as potential TSPO PET imaging ligands. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.057
• 作为产物：
  描述：

  4-氧代硫代苯并二氢吡喃-2-羧酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 (+/-)-4-Oxo-thiochroman-2-carboxylic acid diethyl amide
  参考文献：
  名称：

  [EN] S-ENANTIOMER OF TETRACYCLIC INDOLE DERIVATIVE AS PBR LIGANDS
  [FR] ÉNANTIOMÈRE S DE DÉRIVÉ D'INDOLE TÉTRACYCLIQUE EN TANT QUE LIGANDS DE PBR

  摘要：

  本发明涉及体内成像，特别是体内成像转位蛋白（TSPO，曾被称为外周苯二氮平受体）。提供了一种基于吲哚的体内成像剂，克服了与已知的TSPO结合放射性示踪剂相关的问题。本发明还提供了一种前体化合物，可用于合成本发明的体内成像剂，以及一种合成所述前体化合物的方法。本发明的其他方面包括一种合成本发明的体内成像剂的方法，包括使用本发明的前体化合物，用于执行该方法的工具箱，以及用于执行该方法的自动化版本的盒子。此外，本发明还提供了一种放射性药物组合物，包括本发明的体内成像剂，以及使用所述体内成像剂的方法。

  公开号：

  WO2015040151A1

文献信息

• Indole derivatives
  申请人：GE Healthcare Limited

  公开号：US09220795B2

  公开（公告）日：2015-12-29

  An indole-based in vivo imaging agent is provided by the present invention that binds with high affinity to PBR, has good uptake into the brain following administration, and which has good selective binding to PBR. The invention also includes a precursor compound useful in the synthesis of the in vivo imaging agent of the invention, as well as a method for synthesis of said in vivo imaging agent comprising use of said precursor compound, and a kit for carrying out said method. Also provided is a cassette for automated synthesis of the in vivo imaging agent. Further aspects of the invention include a radiopharmaceutical composition comprising the in vivo imaging agent of the invention, and methods for the use of said in vivo imaging agent.

  本发明提供了一种吲哚基体内成像剂，该成像剂与PBR具有高亲和力，给药后能够良好地进入大脑，并且对PBR具有优良的选择性结合。本发明还包括用于合成本发明的体内成像剂的先驱化合物，以及一种使用所述先驱化合物的合成所述体内成像剂的方法，以及用于执行所述方法的试剂盒。还提供了一种用于自动合成体内成像剂的盒式磁带。发明的进一步方面包括一种放射性药物组合物，该组合物包含本发明的体内成像剂，以及使用所述体内成像剂的方法。
• Design, synthesis, and structure–activity relationships of novel tetracyclic compounds as peripheral benzodiazepine receptor ligands
  作者：Taketoshi Okubo、Ryoko Yoshikawa、Shigeyuki Chaki、Shigeru Okuyama、Atsuro Nakazato

  DOI：10.1016/j.bmc.2004.04.025

  日期：2004.7

  The peripheral benzodiazepine receptor (PBR) is pharmacologically distinct from the central benzodiazepine receptor (CBR) and has been identified in a wide range of peripheral tissues as well as in the central nervous system. Although numerous studies have been performed of it, the physiological roles and functions of the PBR are still unclear. In the present study, in exploring new types of ligands

  外周苯二氮卓类受体（PBR）在药理上不同于中枢苯二氮卓类受体（CBR），并且已在广泛的外周组织以及中枢神经系统中得到鉴定。尽管已经对其进行了大量研究，但是PBR的生理作用和功能仍不清楚。在本研究中，在探索新型的PBR配体时，我们发现由FGIN-1-27设计的一系列具有四环系统的新化合物对PBR表现出高亲和力。我们准备并评估了它们的PBR亲和力。结合测试的结果表明，12e和12f是其中最有效的PBR配体（12e：IC（50）= 0.44nM，12f：IC（50）= 0.37nM）。在本文中，我们介绍了设计，综合，
• INDOLE DERIVATIVES
  申请人：GE HEALTHCARE LIMITED

  公开号：US20140364615A1

  公开（公告）日：2014-12-11

  An indole-based in vivo imaging agent is provided by the present invention that binds with high affinity to PBR, has good uptake into the brain following administration, and which has good selective binding to PBR. The invention also includes a precursor compound useful in the synthesis of the in vivo imaging agent of the invention, as well as a method for synthesis of said in vivo imaging agent comprising use of said precursor compound, and a kit for carrying out said method. Also provided is a cassette for automated synthesis of the in vivo imaging agent. Further aspects of the invention include a radiopharmaceutical composition comprising the in vivo imaging agent of the invention, and methods for the use of said in vivo imaging agent.

  本发明提供了一种基于吲哚的体内成像剂，它与PBR具有高亲和力，且在给药后具有良好的大脑摄取能力，并且对PBR具有很好的选择性结合。本发明还包括一种在合成该体内成像剂中有用的前体化合物，以及一种合成所述体内成像剂的方法，包括使用所述前体化合物，并提供了用于执行该方法的工具包。此外，本发明还提供了一种用于自动合成体内成像剂的盒式装置。本发明的其他方面包括包含所述体内成像剂的放射性药物组合物，以及使用所述体内成像剂的方法。
• TETRACYCLIC INDOLE DERIVATIVES AS IN VIVO IMAGING AGENTS AND HAVING PERIPHERALBENZODIAZEPINE RECEPTOR AFFINITY (PBR)
  申请人：Arstad Erik

  公开号：US20090220420A1

  公开（公告）日：2009-09-03

  The present invention provides novel tetracyclic indole compounds of Formula (I) either as in vivo imaging agents or as therapeutic agents. A method for the preparation of the in vivo imaging agent compound is also provided by the invention, as well as a precursor for use in said method. Pharmaceutical compositions comprising the compounds of the invention are additionally provided. Where the pharmaceutical composition comprises a compound suitable for in vivo imaging, a kit is provided for the preparation of the pharmaceutical composition. In a further aspect, use of the compound for in vivo imaging or treatment of conditions associated with PBR is provided.

  本发明提供了新型四环吲哚化合物（I）作为体内成像剂或治疗剂。本发明还提供了一种用于制备体内成像剂化合物的方法，以及用于该方法的前体。此外，还提供了包含本发明化合物的制药组合物。其中，如果制药组合物包含适用于体内成像的化合物，则提供用于制备制药组合物的工具包。在另一个方面，提供了将该化合物用于体内成像或治疗与PBR相关病症的用途。
• IMAGING NEUROINFLAMMATION
  申请人：Wadsworth Harry John

  公开号：US20110190618A1

  公开（公告）日：2011-08-04

  The present invention concerns in vivo imaging and in particular in vivo imaging of the peripheral benzodiazepine receptor (PBR). A tetracyclic indole in vivo imaging agent is provided that binds with high affinity to PBR, has good uptake into the brain following administration, and which preferentially binds to tissues expressing higher levels of PBR. The present invention also provides a precursor compound useful in the synthesis of the in vivo imaging agent of the invention, as well as a method for synthesis of said in vivo imaging agent comprising use of said precursor compound, and a kit for carrying out said method. A cassette for the automated synthesis of the in vivo imaging agent is also provided. In addition, the invention provides a radiopharmaceutical composition comprising the in vivo imaging agent of the invention, as well as methods for the use of said in vivo imaging agent.

  本发明涉及体内成像，特别是外周苯二氮平受体（PBR）的体内成像。提供了一种四环吲哚体内成像试剂，它具有高亲和力结合PBR，在给药后良好地吸收到大脑，并且优先结合表达更高水平PBR的组织。本发明还提供了用于合成本发明的体内成像试剂的前体化合物，以及一种合成上述体内成像试剂的方法，包括使用该前体化合物，并提供用于执行该方法的试剂盒。还提供了一种用于自动合成体内成像试剂的盒子。此外，本发明还提供了包含本发明的体内成像试剂的放射性药物组合物，以及使用该体内成像试剂的方法。