4-oxothiochroman-2-carbonyl chloride

• 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-oxothiochroman-2-carbonyl chloride
• 英文别名: 4-Oxothiochroman-2-carbonyl chloride；4-oxo-2,3-dihydrothiochromene-2-carbonyl chloride
• 化学式: C₁₀H₇ClO₂S
• 分子量: 226.683
• InChiKey: WHOJJPMDAFVMDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-oxothiochroman-2-carbonyl chloride 在 硫酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 8-ethoxy-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 2.0h， 生成 4-oxothiochroman-2-carbonyl chloride
  参考文献：
  名称：

  苯并噻喃衍生物抗利什曼原虫和细胞毒活性的合成与评价

  摘要：

  为了继续努力确定基于色满支架的有希望的抗利什曼试剂，我们合成了几种取代的 2H-硫色满衍生物，包括在 C-2 或 C-3 中被羰基或羧基取代的硫色烯、硫色满酮和腙。因此获得、表征和评估了 32 种化合物，并针对 Leishmania (V) panamensis 的细胞内无鞭毛体进行了评估。12 种化合物具有活性，EC50 值低于 40 µM，但只有四种化合物显示出最高的抗利什曼原虫活性，EC50 值低于 10 µM；这些所有化合物都具有良好的选择性指数 > 2.6。尽管两种活性化合物是硫色素，但由于每种活性化合物具有不同的取代模式，因此未检测到明确的构效关系。

  DOI：

  10.3390/molecules25040800

文献信息

• [EN] S-ENANTIOMER OF TETRACYCLIC INDOLE DERIVATIVE AS PBR LIGANDS<br/>[FR] ÉNANTIOMÈRE S DE DÉRIVÉ D'INDOLE TÉTRACYCLIQUE EN TANT QUE LIGANDS DE PBR
  申请人：GE HEALTHCARE LTD

  公开号：WO2015040151A1

  公开（公告）日：2015-03-26

  The present invention concerns in vivo imaging and in particular in vivo imaging of translocator protein (TSPO, formerly known as the peripheral benzodiazepine receptor). An indole-based in vivo imaging agent is provided that overcomes problems relating to known TSPO-binding radiotracers. The present invention also provides a precursor compound useful in the synthesis of the in vivo imaging agent of the invent ion, as well as a method for synthesis of said precursor compound. Other aspects of the invention include a method for the synthesis of the in vivo imaging agent of the invention comprising use of the precursor compound of the invention, a kit for carrying out said method, and a cassette for carrying out an automated version of said method. 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。
• S-ENANTIOMER OF TETRACYCLIC INDOLE DERIVATIVE AS PBR LIGANDS
  申请人：GE HEALTHCARE LIMITED

  公开号：US20160222024A1

  公开（公告）日：2016-08-04

  The present invention concerns in vivo imaging and in particular in vivo imaging of translocator protein (TSPO, formerly known as the peripheral benzodiazepine receptor). An indole-based in vivo imaging agent is provided that overcomes problems relating to known TSPO-binding radiotracers. 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 precursor compound. Other aspects of the invention include a method for the synthesis of the in vivo imaging agent of the invention comprising use of the precursor compound of the invention, a kit for carrying out said method, and a cassette for carrying out an automated version of said method. 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，特别是体内成像转运蛋白（TSPO，曾称外周苯二氮平受体）。提供了一种基于吲哚的体内成像剂，能够克服与已知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使用本发明的前体化合物合成本发明的体内成像剂的方法，用于执行该方法的试剂盒，以及用于执行该方法的自动化版本的盒子。此外，本发明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。
• [EN] INDOLE DERIVATIVES SUITABLE FOR IMAGING NEUROINFLAMMATION<br/>[FR] IMAGERIE DE NEURO-INFLAMMATION
  申请人：GE HEALTHCARE LTD

  公开号：WO2010037851A3

  公开（公告）日：2010-07-01
• Synthesis and Evaluation of Antileishmanial and Cytotoxic Activity of Benzothiopyrane Derivatives
  作者：Cristian Ortiz、Fernando Echeverri、Sara Robledo、Daniela Lanari、Massimo Curini、Wiston Quiñones、Esteban Vargas

  DOI：10.3390/molecules25040800

  日期：——

  In continuation of our efforts to identify promising antileishmanial agents based on the chroman scaffold, we synthesized several substituted 2H-thiochroman derivatives, including thiochromenes, thichromanones and hydrazones substituted in C-2 or C-3 with carbonyl or carboxyl groups. Thirty-two compounds were thus obtained, characterized, and evaluated against intracellular amastigotes of Leishmania

  为了继续努力确定基于色满支架的有希望的抗利什曼试剂，我们合成了几种取代的 2H-硫色满衍生物，包括在 C-2 或 C-3 中被羰基或羧基取代的硫色烯、硫色满酮和腙。因此获得、表征和评估了 32 种化合物，并针对 Leishmania (V) panamensis 的细胞内无鞭毛体进行了评估。12 种化合物具有活性，EC50 值低于 40 µM，但只有四种化合物显示出最高的抗利什曼原虫活性，EC50 值低于 10 µM；这些所有化合物都具有良好的选择性指数 > 2.6。尽管两种活性化合物是硫色素，但由于每种活性化合物具有不同的取代模式，因此未检测到明确的构效关系。
• Exploration of the structure–activity relationship of a novel tetracyclic class of TSPO ligands—Potential novel positron emitting tomography imaging agents
  作者：Dennis O’Shea、Rabia Ahmad、Erik Årstad、Michelle Avory、Wai-Fung Chau、Clare Durrant、Ella Hirani、Paul A. Jones、Imtiaz Khan、Sajinder K. Luthra、Dimitrios Mantzilas、Véronique Morisson-Iveson、Joanna Passmore、Edward G. Robins、Bo Shan、Harry Wadsworth、Sarah Walton、Yongjun Zhao、William Trigg

  DOI：10.1016/j.bmcl.2013.02.057

  日期：2013.4

  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.