methyl 3-amino-6-(2-phenylethynyl)thieno[3,2-b]pyridine-2-carboxylate | 1206907-53-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: methyl 3-amino-6-(2-phenylethynyl)thieno[3,2-b]pyridine-2-carboxylate
• CAS: 1206907-53-0
• 化学式: C₁₇H₁₂N₂O₂S
• 分子量: 308.36
• InChiKey: WDFFZJVCSLOIAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以70%的产率得到methyl 3-amino-6-(2-phenylethynyl)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

• 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。
• Synthesis and evaluation of tumor cell growth inhibition of methyl 3-amino-6-[(hetero)arylethynyl]thieno[3,2-b]pyridine-2-carboxylates. Structure–activity relationships, effects on the cell cycle and apoptosis
  作者：Maria-João R.P. Queiroz、Ricardo C. Calhelha、Luís A. Vale-Silva、Eugénia Pinto、Gabriela M. Almeida、M. Helena Vasconcelos

  DOI：10.1016/j.ejmech.2010.11.009

  日期：2011.1

  The methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate, recently reported by some of us, was reacted in Sonogashira couplings with several (hetero)arylacetylenes. The growth inhibitory activity of the novel methyl 3-amino-6-[(hetero)arylethynyl]thieno[3,2-b]pyridine-2-carboxylates obtained was evaluated on three human tumor cell lines (MCF-7, NCI-H460, A375-C5). The para-methoxyphenyl and the ortho- and para-aminophenyl derivatives were the most promising compounds, and their effects were further studied regarding alterations in the normal cell cycle distribution and induction of apoptosis in the NCI-H460 cell line. All three compounds altered cell cycle distribution and the ortho-aminophenyl derivative was further shown to induce apoptosis in the same cell line. (C) 2010 Elsevier Masson SAS. All rights reserved.