methyl 6-(3-methoxyphenoxy)-3-aminothieno[3,2-b]pyridine-2-carboxylate | 1383792-11-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-(3-methoxyphenoxy)-3-aminothieno[3,2-b]pyridine-2-carboxylate
• 英文别名: Methyl 3-amino-6-(3-methoxyphenoxy)thieno[3,2-b]pyridine-2-carboxylate；methyl 3-amino-6-(3-methoxyphenoxy)thieno[3,2-b]pyridine-2-carboxylate
• CAS: 1383792-11-7
• 化学式: C₁₆H₁₄N₂O₄S
• 分子量: 330.364
• InChiKey: LNWHWXHLWXILDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-甲氧基苯酚 、 methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate 在 copper(l) iodide 、 N,N-二甲基甘氨酸 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以53%的产率得到methyl 6-(3-methoxyphenoxy)-3-aminothieno[3,2-b]pyridine-2-carboxylate
  参考文献：
  名称：

  New potential antitumoral di(hetero)arylether derivatives in the thieno[3,2-b]pyridine series: Synthesis and fluorescence studies in solution and in nanoliposomes

  摘要：

  New fluorescent methoxylated di(hetero)arylethers in the thieno[3,2-b]pyridine series were prepared by a copper-catalyzed Ullmann-type C-O coupling of the methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate with ortho, meta and para-methoxyphenols, using N,N-dimethylglycine as the ligand and Cs2CO3 as the base. The compounds obtained were tested for their inhibitory growth activity in three human tumor cell lines MCF-7 (breast adenocarcinoma), A375-05 (melanoma), NCI-H460 (non-small cell lung cancer). The di(hetero)arylethers bearing a methoxy group in the ortho and meta positions showed very low GI(50) values (1.1-2.5 mu M) in all the three tumor cell lines. Their fluorescence properties in solution and when encapsulated in different nanoliposome formulations, composed either by egg-yolk phosphatidylcholine (Egg-PC), dipalmitoyl phosphatidylcholine (DPPC), dimyristoyl phosphatidylglycerol (DMPG), dioctadecyldimethylammonium bromide (DODAB), distearoyl phosphatidylcholine (DSPC), with or without cholesterol (Ch), or distearoyl phosphatidylethanolamine-(polyethylene glycol)2000 (DSPE-PEG), were studied. All compounds can be carried in the hydrophobic region of the liposome membrane. The liposomes with incorporated compounds are nanometric in size (diameter lower than 150 nm) and have generally low polydispersity. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2012.04.007

文献信息

• New potential antitumoral di(hetero)arylether derivatives in the thieno[3,2-b]pyridine series: Synthesis and fluorescence studies in solution and in nanoliposomes
  作者：Maria-João R.P. Queiroz、Sofia Dias、Daniela Peixoto、Ana Rita O. Rodrigues、Andreia D.S. Oliveira、Paulo J.G. Coutinho、Luís A. Vale-Silva、Eugénia Pinto、Elisabete M.S. Castanheira

  DOI：10.1016/j.jphotochem.2012.04.007

  日期：2012.6

  New fluorescent methoxylated di(hetero)arylethers in the thieno[3,2-b]pyridine series were prepared by a copper-catalyzed Ullmann-type C-O coupling of the methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate with ortho, meta and para-methoxyphenols, using N,N-dimethylglycine as the ligand and Cs2CO3 as the base. The compounds obtained were tested for their inhibitory growth activity in three human tumor cell lines MCF-7 (breast adenocarcinoma), A375-05 (melanoma), NCI-H460 (non-small cell lung cancer). The di(hetero)arylethers bearing a methoxy group in the ortho and meta positions showed very low GI(50) values (1.1-2.5 mu M) in all the three tumor cell lines. Their fluorescence properties in solution and when encapsulated in different nanoliposome formulations, composed either by egg-yolk phosphatidylcholine (Egg-PC), dipalmitoyl phosphatidylcholine (DPPC), dimyristoyl phosphatidylglycerol (DMPG), dioctadecyldimethylammonium bromide (DODAB), distearoyl phosphatidylcholine (DSPC), with or without cholesterol (Ch), or distearoyl phosphatidylethanolamine-(polyethylene glycol)2000 (DSPE-PEG), were studied. All compounds can be carried in the hydrophobic region of the liposome membrane. The liposomes with incorporated compounds are nanometric in size (diameter lower than 150 nm) and have generally low polydispersity. (C) 2012 Elsevier B.V. All rights reserved.