ethyl 2-((3-(5-isobutyl-2-sulfamoylthiophen-3-yl)benzyl)(methyl)amino)-2-oxoacetate | 1360149-27-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-((3-(5-isobutyl-2-sulfamoylthiophen-3-yl)benzyl)(methyl)amino)-2-oxoacetate
• CAS: 1360149-27-4
• 化学式: C₂₀H₂₆N₂O₅S₂
• 分子量: 438.569
• InChiKey: JPDDSKIIGCGTRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  106.77
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-((3-(5-isobutyl-2-sulfamoylthiophen-3-yl)benzyl)(methyl)amino)-2-oxoacetate 、 氯甲酸丁酯 在 4-吡咯烷基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以52 mg的产率得到3-[3-((N-ethoxyoxalyl-N-methyl)aminomethyl)phenyl]-5-isobutylthiophene-2-(N-butoxycarbonyl)sulfonamide
  参考文献：
  名称：

  From the First Selective Non-Peptide AT₂ Receptor Agonist to Structurally Related Antagonists

  摘要：

  A para substitution pattern of the phenyl ring is a characteristic feature of the first reported selective AT(2) receptor agonist M024/C21 (1) and all the nonpeptidic AT(2) receptor agonists described so far. Two series of compounds structurally related to 1 but with a meta substitution pattern have now been synthesized and biologically evaluated for their affinity to the AT(1) and AT(2) receptors. A high AT(2)/AT(1) receptor selectivity was obtained with all 41 compounds synthesized, and the majority exhibited K-i ranging from 2 to 100 nM. Five compounds were evaluated for their functional activity at the AT(2) receptor, applying a neurite outgrowth assay in NG108-15 cells.. Notably, four of the five compounds, with representatives from both series, acted as potent AT(2) receptor antagonists. These compounds were found to be considerably more effective than PD 123,319, the standard AT(2) receptor antagonist used in most laboratories. No AT(2) receptor antagonists were previously reported among the derivatives with a para substitution pattern. Hence, by a minor modification of the agonist 1 it could be transformed into the antagonist, compound 38. These compounds should serve as valuable tools in the assessment of the role of the AT(2) receptor in more complex physiological models.

  DOI：

  10.1021/jm2015099
• 作为产物：
  描述：

  间溴苯甲醛 在 sodium tetrahydroborate 、 palladium diacetate 、 potassium carbonate 、 苯甲醚 、 三乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 14.5h， 生成 ethyl 2-((3-(5-isobutyl-2-sulfamoylthiophen-3-yl)benzyl)(methyl)amino)-2-oxoacetate
  参考文献：
  名称：

  From the First Selective Non-Peptide AT₂ Receptor Agonist to Structurally Related Antagonists

  摘要：

  A para substitution pattern of the phenyl ring is a characteristic feature of the first reported selective AT(2) receptor agonist M024/C21 (1) and all the nonpeptidic AT(2) receptor agonists described so far. Two series of compounds structurally related to 1 but with a meta substitution pattern have now been synthesized and biologically evaluated for their affinity to the AT(1) and AT(2) receptors. A high AT(2)/AT(1) receptor selectivity was obtained with all 41 compounds synthesized, and the majority exhibited K-i ranging from 2 to 100 nM. Five compounds were evaluated for their functional activity at the AT(2) receptor, applying a neurite outgrowth assay in NG108-15 cells.. Notably, four of the five compounds, with representatives from both series, acted as potent AT(2) receptor antagonists. These compounds were found to be considerably more effective than PD 123,319, the standard AT(2) receptor antagonist used in most laboratories. No AT(2) receptor antagonists were previously reported among the derivatives with a para substitution pattern. Hence, by a minor modification of the agonist 1 it could be transformed into the antagonist, compound 38. These compounds should serve as valuable tools in the assessment of the role of the AT(2) receptor in more complex physiological models.

  DOI：

  10.1021/jm2015099