3-(2-methoxyethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine hydrobromide | 959600-28-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2-methoxyethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine hydrobromide
• 英文别名: 3-(2-methoxyethyl)-4,5-dimethyl-1,3-thiazol-2-imine;hydrobromide
• CAS: 959600-28-3
• 化学式: BrH*C₈H₁₄N₂OS
• 分子量: 267.19
• InChiKey: DOZYUNRWQDBWKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  61.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-methoxyethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine hydrobromide 在 lithium aluminium tetrahydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 3-(hydroxymethyl)-N-(3-(2-methoxyethyl)-4,5-dimethylthiazol-2(3H)-ylidene)-2,2-dimethylcyclopropanecarboxamide
  参考文献：
  名称：

  Development of a High-Affinity PET Radioligand for Imaging Cannabinoid Subtype 2 Receptor

  摘要：

  Cannabinoid receptors type 2 (CB2) represent a target with increasing importance for neuroimaging due to its upregulation under various pathological conditions. Encouraged by preliminary results obtained with [C-11](Z)-N-(3- (2-methoxyethyl)-4,5-dimethylthiazol-2(3H)-ylidene)-2,2,3,3-tetramethyl-cyclopropanecarboxamide ([C-11]A-836339, [C-11]1) in a mouse model of acute neuroinflammation (induced by lipopolysaccharide, LPS), we designed a library of fluorinated analogs aiming for an [F-18]-labeled radiotracer with improved CB2 binding affinity and selectivity. Compound (Z)-N-(3-(4-fluorobutyl)-4,5-dimethylthiazol-2(3H)-ylidene)-2,2,3,3-tetramethyl-cyclopropanecarboxamide (29) was selected as a ligand with the highest CB2 affinity (K-i = 0.39 nM) and selectivity over CB1 (factor 1000). [F-18]29 was prepared starting from the bromo precursor (53). Specific binding was shown in vitro whereas fast metabolism was observed in vivo in CD-1 mice. Animal PET revealed a brain uptake comparable to [C-11]1. In the LPS treated mice, a 20-30% higher uptake in brain was found in comparison to non-treated mice (n = 3, P < 0.05).

  DOI：

  10.1021/acs.jmedchem.6b00554
• 作为产物：
  描述：

  2-氨基-4,5-二甲基噻唑 、 2-溴乙基甲基醚 反应 12.0h， 以56%的产率得到3-(2-methoxyethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine hydrobromide
  参考文献：
  名称：

  [EN] NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS AND USES THEREOF
  [FR] NOUVEAUX COMPOSÉS EN TANT QUE LIGANDS DE RÉCEPTEUR DE CANNABINOÏDE ET LEURS UTILISATIONS

  摘要：

  本发明涉及式(I)的化合物，或药用盐、前药、前药的盐或其组合物，式(I)。其中R1、R2、R3、R4和L1在规范中定义，包括含有这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。本发明还涉及式(II)的化合物，或药用盐、前药、前药的盐或其组合物，式(II)。其中R1a、R2a、Rx和n如规范中定义，包括含有这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。

  公开号：

  WO2009067613A1

文献信息

• NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS AND USES THEREOF
  申请人：Florjancic S. Alan

  公开号：US20080058335A1

  公开（公告）日：2008-03-06

  The present invention relates to compounds of formula (I), or pharmaceutical salts, prodrugs, salts of prodrugs, or combinations thereof, wherein R 1 , R 2 , R 3 , and L 1 are defined in the specfication, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions. The present invention also relates to compounds of formula (II), or pharmaceutical salts, prodrugs, salts of prodrugs, or combinations thereof, wherein R 1a , R 2a and (Rx)n are as defined in the specification, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

  本发明涉及式(I)的化合物，或药用盐、前药、前药的盐或其组合物， 其中R 1 ，R 2 ，R 3 和L 1 在规范中定义，包含这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。本发明还涉及式(II)的化合物，或药用盐、前药、前药的盐或其组合物， 其中R 1a ，R 2a 和(Rx)n如规范中定义，包含这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。
• NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS
  申请人：Kolasa Teodozyj

  公开号：US20080242654A1

  公开（公告）日：2008-10-02

  The present application relates to thiazolylidene containing compounds of formula (I) wherein R 1 , R 2 , R 3 , R 4 , L 2 and A are as defined in the specification. Compositions comprising such compounds, and methods for treating conditions and disorders using such compounds and compositions are also disclosed.

  本申请涉及具有以下式（I）的含噻唑基烯醇化合物，其中R1、R2、R3、R4、L2和A如规范中所定义。还公开了包含这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。
• Compounds as cannabinoid receptor ligands
  申请人：Abbott Laboratories

  公开号：US07875640B2

  公开（公告）日：2011-01-25

  The present application relates to thiazolylidene containing compounds of formula (I) wherein R1, R2, R3, R4, L2 and A are as defined in the specification. Compositions comprising such compounds, and methods for treating conditions and disorders using such compounds and compositions are also disclosed.

  本申请涉及公式（I）中含有噻唑烯基的化合物，其中R1、R2、R3、R4、L2和A如规范中所定义。还公开了包含这种化合物的组合物以及使用这种化合物和组合物治疗疾病和疾病的方法。
• Compounds as cannabinoid receptor ligands and uses thereof
  申请人：Abbott Laboratories

  公开号：US07875639B2

  公开（公告）日：2011-01-25

  The present invention relates to compounds of formula (I), or pharmaceutically acceptable salts, prodrugs, salts of prodrugs, or combinations thereof, wherein R1, R2, R3, R4, and L2, are defined in the specification, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

  本发明涉及公式（I）的化合物，或其药学上可接受的盐，前药，前药盐或其组合物，其中R1，R2，R3，R4和L2在规范中定义，包括这样的化合物的组合物，并使用这样的化合物和组合物治疗疾病和病症的方法。
• COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS AND USES THEREOF
  申请人：AbbVie Inc.

  公开号：EP2024349B1

  公开（公告）日：2017-08-02