methyl 3-amino-6-(benzo[d]thiazol-2-ylamino)-thieno[3,2-b]pyridine-2-carboxylate | 1261300-03-1

• 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-(benzo[d]thiazol-2-ylamino)-thieno[3,2-b]pyridine-2-carboxylate
• 英文别名: Methyl 3-amino-6-(benzo[d]thiazol-2-ylamino)thieno[3,2-b]pyridine-2-carboxylate；methyl 3-amino-6-(1,3-benzothiazol-2-ylamino)thieno[3,2-b]pyridine-2-carboxylate
• CAS: 1261300-03-1
• 化学式: C₁₆H₁₂N₄O₂S₂
• 分子量: 356.429
• InChiKey: UBAJZUYTLWGNIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-氨基苯并噻唑 、 methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate 在 palladium diacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以54%的产率得到methyl 3-amino-6-(benzo[d]thiazol-2-ylamino)-thieno[3,2-b]pyridine-2-carboxylate
  参考文献：
  名称：

  Novel 6-[(hetero)arylamino]thieno[3,2-b]pyridines: Synthesis and antitumoral activities

  摘要：

  Several novel 6-[(hetero)arylamino]thieno[3,2-b]pyridines were prepared by palladium-catalyzed C-N Buchwald-Hartwig coupling of the methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate with aryl and heteroarylamines, using different reaction conditions. The antitumoral activity of the di(hetero) arylamines obtained was evaluated against three representative human tumor cell lines, namely breast adenocarcinoma (MCF-7), melanoma (A375-05), and non-small cell lung cancer (NCI-H460) and some structure activity relationships were established within each series. The most promising compounds were shown to be a benzothiazole derivative with GI(50) 3.5-6.9 mu M followed by an indole derivative with GI(50) 13-21 mu M. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.030

文献信息

• Novel 6-[(hetero)arylamino]thieno[3,2-b]pyridines: Synthesis and antitumoral activities
  作者：Maria-João R.P. Queiroz、Ricardo C. Calhelha、Luís A. Vale-Silva、Eugénia Pinto、M. São-José Nascimento

  DOI：10.1016/j.ejmech.2010.09.030

  日期：2010.12

  Several novel 6-[(hetero)arylamino]thieno[3,2-b]pyridines were prepared by palladium-catalyzed C-N Buchwald-Hartwig coupling of the methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate with aryl and heteroarylamines, using different reaction conditions. The antitumoral activity of the di(hetero) arylamines obtained was evaluated against three representative human tumor cell lines, namely breast adenocarcinoma (MCF-7), melanoma (A375-05), and non-small cell lung cancer (NCI-H460) and some structure activity relationships were established within each series. The most promising compounds were shown to be a benzothiazole derivative with GI(50) 3.5-6.9 mu M followed by an indole derivative with GI(50) 13-21 mu M. (C) 2010 Elsevier Masson SAS. All rights reserved.