1-amino-5-chloro-8H-indeno[1,2-c]thiophen-8-one | 473437-49-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-amino-5-chloro-8H-indeno[1,2-c]thiophen-8-one
• 英文别名: 3-amino-7-chloroindeno[1,2-c]thiophen-4-one
• CAS: 473437-49-9
• 化学式: C₁₁H₆ClNOS
• 分子量: 235.694
• InChiKey: VBXISNIKCIZGBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  0
• 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

• 作为反应物：
  描述：

  1-amino-5-chloro-8H-indeno[1,2-c]thiophen-8-one 在 N-(8-oxo-8H-indeno[1,2-c]thiophen-1-yl)acetamide 、 乙酸酐 作用下， 以75%的产率得到N-(5-chloro-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
• 作为产物：
  描述：

  2-(2-carboxybenzamido)-4-(3-chlorophenyl)thiophene-3-carboxylic acid 在 草酰氯 、 N,N-二甲基甲酰胺 、 aluminum (III) chloride 、 一水合肼 作用下， 以 二氯甲烷 、 1,4-二氧六环 为溶剂， 反应 4.0h， 以55%的产率得到1-amino-5-chloro-8H-indeno[1,2-c]thiophen-8-one
  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

• Pharmaceutically active compounds and methods of use
  申请人：——

  公开号：US20030073733A1

  公开（公告）日：2003-04-17

  New fused thiophene compounds are provided and methods of using those compounds for a variety of therapeutic indications. Compounds of the invention are particularly useful for treatment of neuropathic pain.

  提供了新的融合噻吩化合物，并提供了使用这些化合物治疗各种治疗适应症的方法。该发明的化合物特别适用于治疗神经病性疼痛。
• PHARMACEUTICALLY ACTIVE COMPOUNDS AND METHODS OF USE
  申请人：King Pharmaceuticals, Inc.

  公开号：EP1383463A2

  公开（公告）日：2004-01-28
• EP1383463A4
  申请人：——

  公开号：EP1383463A4

  公开（公告）日：2009-03-25
• FUSED THIOPHENE COMPOUNDS AND USE THEREOF IN THE TREATMENT OF CHRONIC PAIN
  申请人：King Pharmaceuticals, Inc.

  公开号：EP1383463B1

  公开（公告）日：2011-04-27
• US7101905B2
  申请人：——

  公开号：US7101905B2

  公开（公告）日：2006-09-05