Methyl 3-[2-[4-(dimethylamino)phenyl]imidazo[1,2-a]pyridin-6-yl]sulfanylpropanoate | 955376-52-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Methyl 3-[2-[4-(dimethylamino)phenyl]imidazo[1,2-a]pyridin-6-yl]sulfanylpropanoate
• CAS: 955376-52-0
• 化学式: C₁₉H₂₁N₃O₂S
• 分子量: 355.461
• InChiKey: RWXGGIYJYAMLQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 3-[2-[4-(dimethylamino)phenyl]imidazo[1,2-a]pyridin-6-yl]sulfanylpropanoate 、 [18F]fluoromethyl bromide 在 potassium tert-butylate 、 caesium carbonate 作用下， 生成 4-[6-((18F)fluoranylmethylsulfanyl)imidazo[1,2-a]pyridin-2-yl]-N,N-dimethylaniline
  参考文献：
  名称：

  WO2007/124345

  摘要：

  公开号：
• 作为产物：
  描述：

  3-巯基丙酸甲酯 、 4-(6-iodo-imidazo[1,2-a]pyridin-2-yl)-N,N-dimethylbenzenamine 在 tris(dibenzylideneacetone)dipalladium (0) 、 1,1'-bis(diisopropylphosphino)ferrocene N-methyl-N-(trimethylstannyl)methanamine 作用下， 以 四氢呋喃 为溶剂， 100.0 ℃ 、1.72 MPa 条件下， 反应 0.5h， 以70%的产率得到Methyl 3-[2-[4-(dimethylamino)phenyl]imidazo[1,2-a]pyridin-6-yl]sulfanylpropanoate
  参考文献：
  名称：

  Synthesis and Evaluation of N-Methyl and S-Methyl ¹¹C-Labeled 6-Methylthio-2-(4′-N,N-dimethylamino)phenylimidazo[1,2-a]pyridines as Radioligands for Imaging β-Amyloid Plaques in Alzheimer’s Disease

  摘要：

  6-Thiolato-substituted 2-(4'-N,N-dimethylamino)phenylimidazo[1,2-a]pyridines (RS-IMPYs; 1-4) were synthesized as candidates for labeling with carbon-11 (t(1/2) = 20.4 min) and imaging of A(beta) plaques in living human brain using positron emission tomography (PET). K-i values for binding of these ligands to Alzheimer's disease brain homogenates were measured in vitro,against tritium-labeled 6 (Pittsburgh compound B). MeS-IMPY (3, K-i = 7.93 nM) was labeled with carbon-11 at its S- or N-methyl position to give [C-11]7 or [C-11]8, respectively. After injection into rats, [C-11]7 or [C-11]8 gave moderately high brain uptakes of radioactivity followed by rapid washout to low levels. The ratio of radioactivity at maximal uptake to that at 60 min reached 18.7 for [C-11]7. [C-11]7 behaved similarly in mouse and monkey. [C-11]7 also bound selectively to A(beta) plaques in post mortem human Alzheimer's disease brain. Although rapidly metabolized in rat by N-demethylation, [C-11]7 was stable in rat brain homogenates. The ex vivo brain radiometabolites observed in rats have a peripheral origin. Overall, [C-11]7 merits further evaluation in human subjects.

  DOI：

  10.1021/jm700970s

文献信息

• BETA-AMYLOID PET IMAGING AGENTS
  申请人：Cai Lisheng

  公开号：US20110008255A1

  公开（公告）日：2011-01-13

  Novel derivatives of imidazopyridinylbenzeneamines and novel derivatives of benzothiazolylbenzeneamines are disclosed that offer improved behavior when used as imaging agents for positron emission tomography of beta-amyloids. Also disclosed is a palladium-catalyzed reaction scheme under microwave conditions for aryl thioethers in general that provides a high ratio of substitution relative to reduction and can be used for the imidazopyridinylbenzeneamine derivatives as well as other compounds of related structure.

  本发明揭示了新型咪唑吡啶基苯胺衍生物和新型苯并噻唑基苯胺衍生物，用作正电子发射断层扫描成像剂时表现出改进的行为。还揭示了一种钯催化反应方案，在微波条件下对芳基硫醚进行反应，相对于还原提供更高的取代比，并可用于咪唑吡啶基苯胺衍生物以及其他相关结构的化合物。
• Beta-Amyloid Pet Imaging Agents
  申请人：The Government Of The United States, As Represented by The Secretary Of Health And Human Services

  公开号：EP2808020A1

  公开（公告）日：2014-12-03

  A compound having the formula wherein: R11 is a member selected from the group consisting of C1-C6 alkyl, aryl- or halo- substituted C1-C6 alkyl, hydroxyl-substituted C1-C6 alkyl, and carbamoyl C1-C6 alkyl; R12 is a member selected from the group consisting of H, C1-C6 alkyl, halo-substituted C1-C6 alkyl, halo, and C1-C6 alkylthio, and R13 is a member selected from the group consisting of H and C1-C3 alkyl, or R12 and R13 are joined to form a thio-C1-C3 alkylene or alkylene linkage, and R14 is a member selected from the group consisting of H and C1-C6 alkyl, and X is CH or N.

  一种化合物，其化学式为 其中 R11 是选自由 C1-C6 烷基、芳基或卤代 C1-C6 烷基、羟基取代的 C1-C6 烷基和卤代 C1-C6 烷基组成的组。 取代的 C1-C6 烷基、羟基取代的 C1-C6 烷基和 氨基甲酰基 C1-C6 烷基； R12 是选自 H、C1-C6 烷基、卤代 C1-C6 烷基、卤代 C1-C6 烷基、卤代 C1-C6 烷基和氨基甲酰基 C1-C6 烷基的成员 C1-C6烷基、卤代和 C1-C6 烷硫基，R13 是选自 H 和 C1-C3 烷基组成的组的成员，或 R12 和 R13 连接形成硫代-C1-C3 亚烷基或亚烷基连接，R14 是选自 H 和 C1-C6 烷基组成的组的成员，X 是 CH 或 N。
• US20140341812A1
  申请人：——

  公开号：US20140341812A1

  公开（公告）日：2014-11-20
• US8703096B2
  申请人：——

  公开号：US8703096B2

  公开（公告）日：2014-04-22
• [EN] BETA-AMYLOID PET IMAGING AGENTS<br/>[FR] AGENTS D'IMAGERIE TEP DE BÊTA-AMYLOÏDES
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2007124345A2

  公开（公告）日：2007-11-01

  [EN] Novel derivatives of imidazopyridinylbenzeneamines and novel derivatives of benzothiazolylbenzeneamines are disclosed that offer improved behavior when used as imaging agents for positron emission tomography of beta-amyloids. Also disclosed is a palladium-catalyzed reaction scheme under microwave conditions for aryl thioethers in general that provides a high ratio of substitution relative to reduction and can be used for the imidazopyridinylbenzeneamine derivatives as well as other compounds of related structure.
  [FR] La présente invention porte sur de nouveaux dérivés d'imidazopyridinylbenzèneamine et de nouveaux dérivés de benzothiazolylbenzèneamine dont l'utilité est améliorée lors de leur utilisation en tant qu'agents d'imagerie pour tomographie par émission de positons de bêta-amyloïdes. La présente invention a également pour objet un schéma réactionnel catalysé par le palladium dans des conditions employant les micro-ondes pour la synthèse générale d'arylthioéthers qui présente un rapport élevé substitution sur réduction et qui peut être employé pour la synthèse des dérivés d'imidazopyridinylbenzèneamine ainsi que d'autres composés de structure proche.