methyl 3-amino-6-(thien-3-yl)thieno[3,2-b]pyridine-2-carboxylate | 1261352-01-5

• 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-(thien-3-yl)thieno[3,2-b]pyridine-2-carboxylate
• 英文别名: methyl 3-amino-6-(3-thienyl)thieno[3,2-b]pyridine-2-carboxylate；Methyl 3-amino-6-thiophen-3-ylthieno[3,2-b]pyridine-2-carboxylate
• CAS: 1261352-01-5
• 化学式: C₁₃H₁₀N₂O₂S₂
• 分子量: 290.367
• InChiKey: YDFGCXUFDWDCMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-amino-6-(thien-3-yl)thieno[3,2-b]pyridine-2-carboxylate 在 亚硝酸特丁酯 、 叠氮基三甲基硅烷 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  通过“点击”铜高效一锅法合成3- [4-（芳基或杂芳基）-1H-1,2,3-三唑-1-基]噻吩并[3,2-b]吡啶-2-羧酸烷基酯（I）催化的叠氮化物-炔烃环加成反应

  摘要：

  摘要 几种新的3- [4-（芳基或杂芳基）-1 H -1,2,3-三唑-1-基]噻吩并[3,2 - b ]吡啶-2-羧酸烷基酯的有效一锅合成具有通过原位叠氮化烷基3-氨基硫代[3,2- b ]吡啶-2-羧酸酯，然后进行Cu（I）催化的叠氮化物-炔烃环加成反应（CuAAC）进行。两种反应均在室温下进行，第一个反应在MeCN中使用亚硝酸叔丁酯和TMSN 3进行2小时，第二个反应在MeCN中使用数个（杂）芳基炔烃，CuI和Et 3 N进行，反应时间非常短（15– 30分钟）。直接使用了活性铜（I）物种，而不是常用的铜（II）物种（CuSO 4）与还原剂（抗坏血酸钠）原位生成Cu（I），在我们的案例中不起作用。这种一锅法显示的范围很广，可以高至高收率获得可能具有生物学活性的产物，而无需进行色谱纯化，从而满足“点击”化学的标准。据我们所知，这是首次将使用这些条件的方法应用于杂环部分。 几种新的3- [4-（芳基或杂芳基）-1

  DOI：

  10.1055/s-0035-1562093
• 作为产物：
  描述：

  methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate 、 3-噻吩三氟硼酸钾 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， 反应 3.0h， 以80%的产率得到methyl 3-amino-6-(thien-3-yl)thieno[3,2-b]pyridine-2-carboxylate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2010.09.014

文献信息

• Efficient One-Pot Synthesis of Alkyl 3-[4-(Aryl or Heteroaryl)-1H-1,2,3-triazol-1-yl]thieno[3,2-b]pyridine-2-carboxylates by ‘Click’ Cu(I)-Catalyzed Azide–Alkyne Cycloaddition
  作者：Maria-João Queiroz、Juliana Rodrigues

  DOI：10.1055/s-0035-1562093

  日期：——

  criteria of ‘click’ chemistry. To our knowledge it is the first time that this methodology, using these conditions, has been applied to a heterocyclic moiety. An efficient one-pot synthesis of several new alkyl 3-[4-(aryl or heteroaryl)-1H-1,2,3-triazol-1-yl]thieno[3,2-b]pyridine-2-carboxylates has been performed by in situ azidation of alkyl 3-aminothieno[3,2-b]pyridine-2-carboxylates followed by Cu(I)-catalyzed

  摘要 几种新的3- [4-（芳基或杂芳基）-1 H -1,2,3-三唑-1-基]噻吩并[3,2 - b ]吡啶-2-羧酸烷基酯的有效一锅合成具有通过原位叠氮化烷基3-氨基硫代[3,2- b ]吡啶-2-羧酸酯，然后进行Cu（I）催化的叠氮化物-炔烃环加成反应（CuAAC）进行。两种反应均在室温下进行，第一个反应在MeCN中使用亚硝酸叔丁酯和TMSN 3进行2小时，第二个反应在MeCN中使用数个（杂）芳基炔烃，CuI和Et 3 N进行，反应时间非常短（15– 30分钟）。直接使用了活性铜（I）物种，而不是常用的铜（II）物种（CuSO 4）与还原剂（抗坏血酸钠）原位生成Cu（I），在我们的案例中不起作用。这种一锅法显示的范围很广，可以高至高收率获得可能具有生物学活性的产物，而无需进行色谱纯化，从而满足“点击”化学的标准。据我们所知，这是首次将使用这些条件的方法应用于杂环部分。 几种新的3- [4-（芳基或杂芳基）-1
• 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.