methyl 3-amino-6-[2-(thien-3-yl)ethynyl]thieno[3,2-b]pyridine-2-carboxylate | 1263093-27-1

• 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-[2-(thien-3-yl)ethynyl]thieno[3,2-b]pyridine-2-carboxylate
• 英文别名: Methyl 3-amino-6-(2-thiophen-3-ylethynyl)thieno[3,2-b]pyridine-2-carboxylate
• CAS: 1263093-27-1
• 化学式: C₁₅H₁₀N₂O₂S₂
• 分子量: 314.389
• InChiKey: NBOGZLMGFLSMPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  3-乙炔基噻吩 、 methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以70%的产率得到methyl 3-amino-6-[2-(thien-3-yl)ethynyl]thieno[3,2-b]pyridine-2-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of tumor cell growth inhibition of methyl 3-amino-6-[(hetero)arylethynyl]thieno[3,2-b]pyridine-2-carboxylates. Structure–activity relationships, effects on the cell cycle and apoptosis

  摘要：

  The methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate, recently reported by some of us, was reacted in Sonogashira couplings with several (hetero)arylacetylenes. The growth inhibitory activity of the novel methyl 3-amino-6-[(hetero)arylethynyl]thieno[3,2-b]pyridine-2-carboxylates obtained was evaluated on three human tumor cell lines (MCF-7, NCI-H460, A375-C5). The para-methoxyphenyl and the ortho- and para-aminophenyl derivatives were the most promising compounds, and their effects were further studied regarding alterations in the normal cell cycle distribution and induction of apoptosis in the NCI-H460 cell line. All three compounds altered cell cycle distribution and the ortho-aminophenyl derivative was further shown to induce apoptosis in the same cell line. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.009

文献信息

• Synthesis and evaluation of tumor cell growth inhibition of methyl 3-amino-6-[(hetero)arylethynyl]thieno[3,2-b]pyridine-2-carboxylates. Structure–activity relationships, effects on the cell cycle and apoptosis
  作者：Maria-João R.P. Queiroz、Ricardo C. Calhelha、Luís A. Vale-Silva、Eugénia Pinto、Gabriela M. Almeida、M. Helena Vasconcelos

  DOI：10.1016/j.ejmech.2010.11.009

  日期：2011.1

  The methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate, recently reported by some of us, was reacted in Sonogashira couplings with several (hetero)arylacetylenes. The growth inhibitory activity of the novel methyl 3-amino-6-[(hetero)arylethynyl]thieno[3,2-b]pyridine-2-carboxylates obtained was evaluated on three human tumor cell lines (MCF-7, NCI-H460, A375-C5). The para-methoxyphenyl and the ortho- and para-aminophenyl derivatives were the most promising compounds, and their effects were further studied regarding alterations in the normal cell cycle distribution and induction of apoptosis in the NCI-H460 cell line. All three compounds altered cell cycle distribution and the ortho-aminophenyl derivative was further shown to induce apoptosis in the same cell line. (C) 2010 Elsevier Masson SAS. All rights reserved.