3-amino-2-(4-methoxybenzoyl)-6-methyl-4-(3,4,5-trimethoxyphenyl)thieno[2,3-b]pyridine-5-carboxylic acid 2-propoxyethyl ester

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-amino-2-(4-methoxybenzoyl)-6-methyl-4-(3,4,5-trimethoxyphenyl)thieno[2,3-b]pyridine-5-carboxylic acid 2-propoxyethyl ester
• 英文别名: 2-Propoxyethyl 3-amino-2-(4-methoxybenzoyl)-6-methyl-4-(3,4,5-trimethoxyphenyl)thieno[2,3-b]pyridine-5-carboxylate；2-propoxyethyl 3-amino-2-(4-methoxybenzoyl)-6-methyl-4-(3,4,5-trimethoxyphenyl)thieno[2,3-b]pyridine-5-carboxylate
• 化学式: C₃₁H₃₄N₂O₈S
• 分子量: 594.686
• InChiKey: AITMMBKSZSRCAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  157
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  3-oxo-2-[1-(3,4,5-trimethoxyphenyl)-methylidene]butyric acid 2-propoxyethyl ester 在 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 0.58h， 生成 3-amino-2-(4-methoxybenzoyl)-6-methyl-4-(3,4,5-trimethoxyphenyl)thieno[2,3-b]pyridine-5-carboxylic acid 2-propoxyethyl ester
  参考文献：
  名称：

  Thieno[2,3-b]pyridines—A new class of multidrug resistance (MDR) modulators

  摘要：

  To identify new potent multidrug resistance modulators, we have synthesized a series of novel thieno[ 2,3-b]pyridines and furo[2,3-b] pyridines, and examined their stucture-activity relationships. All synthesized compounds were tested to determine BCRP1, P-gp, and MRP1 inhibitor activity, and most potent MDR modulators were also screened for their toxicity, cytotoxicity and Ca2+ channel antagonist activity. Among these compounds, thieno[2,3-b] pyridine (6r) was found to exhibit a potent P-gp inhibitory action with EC50 = 0.3 +/- 0.2 mu M, MRP1 inhibitory action with EC50 = 1.1 +/- 0.1 mu M and BCRP1 inhibitory action with EC50 = 0.2 +/- 0.05 mu M and may represent suitable candidate for further pharmacological studies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.023

文献信息

• Thieno[2,3-b]pyridines—A new class of multidrug resistance (MDR) modulators
  作者：Aivars Krauze、Signe Grinberga、Laura Krasnova、Ilze Adlere、Elina Sokolova、Ilona Domracheva、Irina Shestakova、Zigmars Andzans、Gunars Duburs

  DOI：10.1016/j.bmc.2014.09.023

  日期：2014.11

  To identify new potent multidrug resistance modulators, we have synthesized a series of novel thieno[ 2,3-b]pyridines and furo[2,3-b] pyridines, and examined their stucture-activity relationships. All synthesized compounds were tested to determine BCRP1, P-gp, and MRP1 inhibitor activity, and most potent MDR modulators were also screened for their toxicity, cytotoxicity and Ca2+ channel antagonist activity. Among these compounds, thieno[2,3-b] pyridine (6r) was found to exhibit a potent P-gp inhibitory action with EC50 = 0.3 +/- 0.2 mu M, MRP1 inhibitory action with EC50 = 1.1 +/- 0.1 mu M and BCRP1 inhibitory action with EC50 = 0.2 +/- 0.05 mu M and may represent suitable candidate for further pharmacological studies. (C) 2014 Elsevier Ltd. All rights reserved.