methyl 3-amino-6-[6-(2-chloro-5-methoxyphenylamino)-2-(methoxycarbonyl)thieno[3,2-b]pyridin-3-ylamino]thieno[3,2-b]pyridine-2-carboxylate | 1261299-99-3

• 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-[6-(2-chloro-5-methoxyphenylamino)-2-(methoxycarbonyl)thieno[3,2-b]pyridin-3-ylamino]thieno[3,2-b]pyridine-2-carboxylate
• 英文别名: Methyl 3-[(3-amino-2-methoxycarbonylthieno[3,2-b]pyridin-6-yl)amino]-6-(2-chloro-5-methoxyanilino)thieno[3,2-b]pyridine-2-carboxylate
• CAS: 1261299-99-3
• 化学式: C₂₅H₂₀ClN₅O₅S₂
• 分子量: 570.049
• InChiKey: GCNSAHJSWJOGOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  194
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate 、 2-氯-5-甲氧基苯胺盐酸盐 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 22.0h， 以48%的产率得到methyl 3-amino-6-(2-chloro-5-methoxyphenylamino)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.