methyl 3-amino-6-[4-(trifluoromethyl) phenyl]thieno[3,2-b]pyridine-2-carboxylate | 1206907-49-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 3-amino-6-[4-(trifluoromethyl) phenyl]thieno[3,2-b]pyridine-2-carboxylate
• 英文别名: Methyl 3-amino-6-[4-(trifluoromethyl)phenyl]thieno[3,2-b]pyridine-2-carboxylate
• CAS: 1206907-49-4
• 化学式: C₁₆H₁₁F₃N₂O₂S
• 分子量: 352.337
• InChiKey: NMNZAZUOEXYQJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate 、 (4-三氟甲基苯基)三氟硼酸钾 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 以75%的产率得到methyl 3-amino-6-[4-(trifluoromethyl) phenyl]thieno[3,2-b]pyridine-2-carboxylate
  参考文献：
  名称：

  钯催化偶联和分子内环化反应合成新的噻吩并[3,2- b ]吡啶衍生物

  摘要：

  两个甲基3-氨基噻吩并[3,2- b ]吡啶-2-羧酸盐是从3制备-氟或3- nitropicolinonitriles和巯基乙酸甲酯在DMF / KOH（水溶液）。从吡啶环中未取代的前体中，通过C–N Buchwald–Hartwig与溴硝基苯和2-溴吡啶的偶联，获得二（杂）芳基胺。在后一种情况下，通过分子内环化形成四环化合物。使用吡啶环中的溴化衍生物作为偶联成分，可以合成C–C（Suzuki和Sonogashira）和C–N（Buchwald–Hartwig）偶联产物，以及通过噻吩并吡啶系统双官能化获得的四环化合物。

  DOI：

  10.1016/j.tetlet.2009.10.138

文献信息

• Efficient synthesis of 6-(hetero)arylthieno[3,2-b]pyridines by Suzuki–Miyaura coupling. Evaluation of growth inhibition on human tumor cell lines, SARs and effects on the cell cycle
  作者：Maria-João R.P. Queiroz、Ricardo C. Calhelha、Luís A. Vale-Silva、Eugénia Pinto、Raquel T. Lima、M. Helena Vasconcelos

  DOI：10.1016/j.ejmech.2010.09.014

  日期：2010.12

  A wide variety of new bi(hetero)aryl derivatives of the thieno[3,2-b]pyridine skeleton was obtained in high to excellent yields (65-91%) by Suzuki-Miyaura cross-coupling of the methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate, recently reported by us, with aryl or heteroaryl pinacolboranes or potassium trifluoroborates.The coupling products obtained were evaluated for their growth inhibitory effect on three human tumor cell lines, representing different tumor models, MCF-7 (breast adenocarcinoma), A375-05 (melanoma) and NCI-H460 (non-small cell lung cancer). Some of the compounds showed an interesting activity against the tested cell lines, with GI(50) values in the mu M range, and it was possible to establish some structure activity relationships (SARs). Several compounds presented GI(50) values below 15 MM, particularly a bithiophene and an o-aniline thienopyridine derivative. The first presented selectivity for MCF-7 and NCI-H460 cell lines, with very low GI(50) values (0.7-1.0 mu M), while the latter was active against the three cell lines tested in this study, also presenting very low GI(50) values (2.5-4.2 mu M). The effect of these two compounds on cell cycle progression was analyzed in the NCI-H460 cell line. Results showed that both compounds interfered with the normal cell cycle distribution. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Synthesis of new thieno[3,2-b]pyridine derivatives by palladium-catalyzed couplings and intramolecular cyclizations
  作者：Ricardo C. Calhelha、Maria-João R.P. Queiroz

  DOI：10.1016/j.tetlet.2009.10.138

  日期：2010.1

  di(hetero)arylamines were obtained by C–N Buchwald–Hartwig coupling with bromonitrobenzenes and with 2-bromopyridine. In the latter case a tetracyclic compound was formed by intramolecular cyclization. Using a brominated derivative in the pyridine ring as a coupling component, it was possible to synthesize C–C (Suzuki and Sonogashira) and C–N (Buchwald–Hartwig) coupling products and a tetracyclic compound obtained

  两个甲基3-氨基噻吩并[3,2- b ]吡啶-2-羧酸盐是从3制备-氟或3- nitropicolinonitriles和巯基乙酸甲酯在DMF / KOH（水溶液）。从吡啶环中未取代的前体中，通过C–N Buchwald–Hartwig与溴硝基苯和2-溴吡啶的偶联，获得二（杂）芳基胺。在后一种情况下，通过分子内环化形成四环化合物。使用吡啶环中的溴化衍生物作为偶联成分，可以合成C–C（Suzuki和Sonogashira）和C–N（Buchwald–Hartwig）偶联产物，以及通过噻吩并吡啶系统双官能化获得的四环化合物。