methyl 3-amino-6-(thien-2-yl)thieno[3,2-b]pyridine-2-carboxylate | 1261352-02-6

• 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-2-yl)thieno[3,2-b]pyridine-2-carboxylate
• 英文别名: Methyl 3-amino-6-thiophen-2-ylthieno[3,2-b]pyridine-2-carboxylate
• CAS: 1261352-02-6
• 化学式: C₁₃H₁₀N₂O₂S₂
• 分子量: 290.367
• InChiKey: GINWTSOYQODQTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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

• 作为产物：
  描述：

  2-溴噻吩 、 methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate 在 palladium diacetate 、 三乙胺 、 频那醇硼烷 、 tri tert-butylphosphoniumtetrafluoroborate 、 barium hydroxide octahydrate 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以70%的产率得到methyl 3-amino-6-(thien-2-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 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.