2-acetyl-3-amino-4-(3,4-dimethoxyphenyl)-6-methylthieno[2,3-b]pyridine-5-carboxylic acid ethyl ester | 1186047-81-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-acetyl-3-amino-4-(3,4-dimethoxyphenyl)-6-methylthieno[2,3-b]pyridine-5-carboxylic acid ethyl ester
• 英文别名: Ethyl 2-acetyl-3-amino-4-(3,4-dimethoxyphenyl)-6-methylthieno[2,3-b]pyridine-5-carboxylate；ethyl 2-acetyl-3-amino-4-(3,4-dimethoxyphenyl)-6-methylthieno[2,3-b]pyridine-5-carboxylate
• CAS: 1186047-81-3
• 化学式: C₂₁H₂₂N₂O₅S
• 分子量: 414.482
• InChiKey: DQYRTPYWRDFIPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  ethyl 5-cyano-4-(3,4-dimethoxyphenyl)-2-methyl-6-thioxo-1,6-dihydropyridine-3-carboxylate 、 溴丙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.58h， 以70%的产率得到2-acetyl-3-amino-4-(3,4-dimethoxyphenyl)-6-methylthieno[2,3-b]pyridine-5-carboxylic acid ethyl 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

• Cyanothioacetamide and Its Derivatives in Heterocyclic Chemistry: Synthesis of Some New Thioxopyridine, Thienopyridine, and Pyridothienopyrimidine Derivatives
  作者：Nada M. Abunada、Ali K. K. El-Louh、Ismaeel S. Al-Zaeem

  DOI：10.1080/10426500802237143

  日期：2009.3.10

  A number of thieno[2,3-b]pyridines ( 9–13 ) and pyridothienopyrimidines ( 14–16 ) were synthesized via the reaction of the dihydrothioxopyridine derivatives ( 7a,b ), obtained by the action of ethyl acetoacetate on arylidine cyanothioacetamide 4 , with halogenated compounds 8a–f .

  许多噻吩并[2,3-b]吡啶（ 9–13 ）和吡啶并噻吩并嘧啶（ 14–16 ）是通过二氢硫代吡啶衍生物（ 7a, b ）的反应合成的，该衍生物是通过乙酰乙酸乙酯对芳基氰硫代乙酰胺4的作用获得的, 与卤代化合物 8a-f 。
• 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.