2-(2-(4-(methylamino)phenyl)-imidazo[1,2-a]pyridin-6-ylthio)ethanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-(4-(methylamino)phenyl)-imidazo[1,2-a]pyridin-6-ylthio)ethanol
• 英文别名: 2-[2-[4-(Methylamino)phenyl]imidazo[1,2-a]pyridin-6-yl]sulfanylethanol
• 化学式: C₁₆H₁₇N₃OS
• 分子量: 299.396
• InChiKey: AZTQUPTXPZMJGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  74.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-Trimethylstannanyl-ethanol 、 4-(6-iodo-H-imidazo[1,2-a]pyridin-2-yl)-N-methylbenzenamine 在 tris(dibenzylideneacetone)dipalladium (0) 作用下， 以 甲苯 为溶剂， 150.0 ℃ 、2.07 MPa 条件下， 反应 0.17h， 以91%的产率得到2-(2-(4-(methylamino)phenyl)-imidazo[1,2-a]pyridin-6-ylthio)ethanol
  参考文献：
  名称：

  Rapid palladium-catalyzed cross-coupling in the synthesis of aryl thioethers under microwave conditions

  摘要：

  A Pd-catalyzed coupling of aromatic iodides or bromides and tin-thiolates under microwave conditions was developed to synthesize aromatic thioethers without concomitant formation of the reduced products. Ligand screening revealed DiPPF and BINAP-Tol as the most generally useful ligands for this transformation. A variety of iodides or bromides were coupled to give the thioethers rapidly (10 min) in 60-95% isolated yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.049

文献信息

• Synthesis and Structure−Affinity Relationships of New 4-(6-Iodo-<i>H</i>-imidazo[1,2-<i>a</i>]pyridin-2-yl)-<i>N</i>-dimethylbenzeneamine Derivatives as Ligands for Human β-Amyloid Plaques
  作者：Lisheng Cai、Jessica Cuevas、Sebastian Temme、Mary M. Herman、Claudio Dagostin、David A. Widdowson、Robert B. Innis、Victor W. Pike

  DOI：10.1021/jm0702231

  日期：2007.9.1

  extensive set of 4-(6-iodo-H-imidazo[1,2-a]pyridin-2-yl)-N-dimethylbenzeneamine (IMPY) derivatives was synthesized and assayed for affinity toward human Abeta plaques. 6-Ethylthio- (12h), 6-cyano- (12e), 6-nitro- (12f), and 6-p-methoxybenzylthio- (15d) analogues were discovered to have high affinity (KI < 10 nM). However, introduction of a hydrophilic thioether group in the 6-position (15a-c, 15e-g) reduced

  合成了一组新的4-（6-碘-H-咪唑并[1,2-a]吡啶-2-基）-N-二甲基苯胺（IMPY）衍生物，并测定了对人Abeta斑块的亲和力。发现6-乙基硫基-（12h），6-氰基-（12e），6-硝基-（12f）和6-对甲氧基苄基硫基-（15d）类似物具有高亲和力（KI <10 nM）。然而，在6-位（15a-c，15e-g）中引入亲水性硫醚基降低或消除了亲和力。在仲N-甲基类似物中，相邻环位置的溴取代基（14a）具有高亲和力（KI = 7.4 nM），而甲基取代基则没有（14c）。对6位非亲水性硫醚取代基的耐受性开辟了开发新的敏感正电子发射断层显像放射配体的可能性，以对阿尔茨海默氏病中的人Abeta斑块进行成像，尤其是考虑到硫醚易于通过S-烷基化反应被碳11或氟18标记。在这项研究中揭示的结构活性关系扩展了对人类Abeta斑块中IMPY样配体结合位点的形貌的了解。
• WO2007/124345
  申请人：——

  公开号：——

  公开（公告）日：——
• Rapid palladium-catalyzed cross-coupling in the synthesis of aryl thioethers under microwave conditions
  作者：Lisheng Cai、Jessica Cuevas、Yi-Yuan Peng、Victor W. Pike

  DOI：10.1016/j.tetlet.2006.04.049

  日期：2006.6

  A Pd-catalyzed coupling of aromatic iodides or bromides and tin-thiolates under microwave conditions was developed to synthesize aromatic thioethers without concomitant formation of the reduced products. Ligand screening revealed DiPPF and BINAP-Tol as the most generally useful ligands for this transformation. A variety of iodides or bromides were coupled to give the thioethers rapidly (10 min) in 60-95% isolated yield. (c) 2006 Elsevier Ltd. All rights reserved.