2-(7-chloro-3-(4-(4-fluorobutoxy)phenyl)-5-methyl-4-oxo-4,5-dihydro-3H-pyridazino[4,5-b]indol-1-yl)-N,N-dimethylacetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(7-chloro-3-(4-(4-fluorobutoxy)phenyl)-5-methyl-4-oxo-4,5-dihydro-3H-pyridazino[4,5-b]indol-1-yl)-N,N-dimethylacetamide
• 英文别名: 2-[7-chloro-3-[4-(4-fluorobutoxy)phenyl]-5-methyl-4-oxopyridazino[4,5-b]indol-1-yl]-N,N-dimethylacetamide
• 化学式: C₂₅H₂₆ClFN₄O₃
• 分子量: 484.958
• InChiKey: ABZIJZLLUATJMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  67.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 6-chloro-1-methyl-1H-indole-2-carboxylate 在 盐酸 、 sodium tetrahydroborate 、 三甲基铝 、 盐酸二甲胺 、 三溴化硼 、 四氯化钛 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 102.5h， 生成 2-(7-chloro-3-(4-(4-fluorobutoxy)phenyl)-5-methyl-4-oxo-4,5-dihydro-3H-pyridazino[4,5-b]indol-1-yl)-N,N-dimethylacetamide
  参考文献：
  名称：

  Synthesis and in vitro characterization of novel fluorinated derivatives of the TSPO 18 kDa ligand SSR180575

  摘要：

  SSR180575 (1) is a high-affinity (0.83 nM) TSPO 18 kDa ligand belonging to the pyridazino[4,5-b]indole-1-acetamides family. Herein we describe the synthesis and in vitro characterization of two series of new fluorinated analogues. Eleven compounds (out of fifteen) displayed nanomolar to subnamolar affinities (0.30-8.1 nM) and high selectivities (Ki(CBR)/Ki(TSPO) > 10(3)). Two derivatives stand out as promising candidates for drug development or use as PET probes for in vivo neuroinflammation imaging, once fluorine-18-labelled. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.033

文献信息

• Synthesis and in vitro characterization of novel fluorinated derivatives of the TSPO 18 kDa ligand SSR180575
  作者：Annelaure Damont、Frank Marguet、Frédéric Puech、Frédéric Dollé

  DOI：10.1016/j.ejmech.2015.07.033

  日期：2015.8

  SSR180575 (1) is a high-affinity (0.83 nM) TSPO 18 kDa ligand belonging to the pyridazino[4,5-b]indole-1-acetamides family. Herein we describe the synthesis and in vitro characterization of two series of new fluorinated analogues. Eleven compounds (out of fifteen) displayed nanomolar to subnamolar affinities (0.30-8.1 nM) and high selectivities (Ki(CBR)/Ki(TSPO) > 10(3)). Two derivatives stand out as promising candidates for drug development or use as PET probes for in vivo neuroinflammation imaging, once fluorine-18-labelled. (C) 2015 Elsevier Masson SAS. All rights reserved.