(2-amino-5-phenylthiophen-3-yl)(4-chlorophenyl)methanone | 1082867-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-amino-5-phenylthiophen-3-yl)(4-chlorophenyl)methanone
• 英文别名: (2-Amino-5-phenylthiophen-3-yl)-(4-chlorophenyl)methanone
• CAS: 1082867-02-4
• 化学式: C₁₇H₁₂ClNOS
• 分子量: 313.807
• InChiKey: RHKSBBGKNMVTEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 生成 (2-amino-5-phenylthiophen-3-yl)(4-chlorophenyl)methanone
  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

文献信息

• SPHINGOSINE-1-PHOSPHATE (S1P) RECEPTOR COMPOUNDS
  申请人：Brussee Johannes

  公开号：US20100317709A1

  公开（公告）日：2010-12-16

  The invention relates to compounds, in particular 2-amino-3,4,5,-trisubstituted thiophenes, pharmaceutical compositions containing them and the uses of said compounds and compositions for diseases related to sphingosine-1-phosphate (S1P) receptors, predominantly S1P3 receptors. The diseases include cardiovascular diseases, atherosclerosis, cancer, pulmonary oedema, autoimmune disorders and Adult Respiratory Distress Syndrome.