N-(3-iodo-8-oxo-8H-indeno[1,2-c]thiophen-1-yl)acetamide | 1245739-64-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(3-iodo-8-oxo-8H-indeno[1,2-c]thiophen-1-yl)acetamide
• 英文别名: N-(1-iodo-4-oxoindeno[1,2-c]thiophen-3-yl)acetamide
• CAS: 1245739-64-3
• 化学式: C₁₃H₈INO₂S
• 分子量: 369.183
• InChiKey: DOOMIZSCMHGMNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  74.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-iodo-8-oxo-8H-indeno[1,2-c]thiophen-1-yl)acetamide 、 4-羧基苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium phosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(1-acetamido-8-oxo-8H-indeno[1,2-c]thiophen-3-yl)benzoic acid
  参考文献：
  名称：

  Effects of Conformational Restriction of 2-Amino-3-benzoylthiophenes on A₁ Adenosine Receptor Modulation

  摘要：

  2-Amino-3-benzoylthiophenes (2A3BTs) have been widely reported to act as allosteric enhancers (A Es) at the A(1) adenosine receptor (A(1)AR). Herein we describe the synthesis of a series of 1-aminoindeno[1,2-c]thiophen-8-ones and a series of (2-aminoindeno[2,1-b]thiophen-3-yl)(phenyl)methanones as conformationally rigid analogues of the 2A3BTs. These compounds were screened using a functional assay of A(1)AR-mediated phosphorylation of extracellular signal-regulated kinases 1 and 2 (ERK 1/2) in intact Chinese hamster ovary (CHO) cells to identify both potential agonistic effects as well as the ability to allosterically modulate the activity of the orthosteric agonist, N-6-(R-phenylisopropyl)adenosine (R-PIA). All of the 1-aminoindeno[1,2-c]thiophen-8-ones (14a-c and 17a-f) proved either to be inactive or behaved as antagonists in the functional assay. However, the (2-aminoindeno[2, 1-b]thiophen-3-yl)(phenyl)methanones with para-chloro substitution (compounds 25b, 25d, and 25f) did significantly augment the R-PIA response, indicating a positive allosteric effect.

  DOI：

  10.1021/jm1008538
• 作为产物：
  描述：

  N-(8-oxo-8H-indeno[1,2-c]thiophen-1-yl)acetamide 在 碘 、 silver nitrate 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 1.0h， 以71%的产率得到N-(3-iodo-8-oxo-8H-indeno[1,2-c]thiophen-1-yl)acetamide
  参考文献：
  名称：

  Effects of Conformational Restriction of 2-Amino-3-benzoylthiophenes on A₁ Adenosine Receptor Modulation

  摘要：

  2-Amino-3-benzoylthiophenes (2A3BTs) have been widely reported to act as allosteric enhancers (A Es) at the A(1) adenosine receptor (A(1)AR). Herein we describe the synthesis of a series of 1-aminoindeno[1,2-c]thiophen-8-ones and a series of (2-aminoindeno[2,1-b]thiophen-3-yl)(phenyl)methanones as conformationally rigid analogues of the 2A3BTs. These compounds were screened using a functional assay of A(1)AR-mediated phosphorylation of extracellular signal-regulated kinases 1 and 2 (ERK 1/2) in intact Chinese hamster ovary (CHO) cells to identify both potential agonistic effects as well as the ability to allosterically modulate the activity of the orthosteric agonist, N-6-(R-phenylisopropyl)adenosine (R-PIA). All of the 1-aminoindeno[1,2-c]thiophen-8-ones (14a-c and 17a-f) proved either to be inactive or behaved as antagonists in the functional assay. However, the (2-aminoindeno[2, 1-b]thiophen-3-yl)(phenyl)methanones with para-chloro substitution (compounds 25b, 25d, and 25f) did significantly augment the R-PIA response, indicating a positive allosteric effect.

  DOI：

  10.1021/jm1008538