3,4-Dimethyl-thiophene-2-carboxylic acid methoxy-methyl-amide | 189745-57-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 3,4-Dimethyl-thiophene-2-carboxylic acid methoxy-methyl-amide
• 英文别名: N-methoxy-N,3,4-trimethylthiophene-2-carboxamide
• CAS: 189745-57-1
• 化学式: C₉H₁₃NO₂S
• 分子量: 199.274
• InChiKey: GXWRQDONNIBITP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  57.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-Dimethyl-thiophene-2-carboxylic acid methoxy-methyl-amide 在 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 2.0h， 生成 (3,4-dimethylthien-2-yl)-1-trityl-imidazol-4-yl-methanol
  参考文献：
  名称：

  α₂ Adrenoceptor Agonists as Potential Analgesic Agents. 3. Imidazolylmethylthiophenes

  摘要：

  A series of imidazolylmethylthiophenes has been prepared and evaluated as ligands for the at adrenoceptor. These compounds were tested in two animal models that are predictive of analgesic activity in humans. The 3-thienyl compounds were generally the most potent, particularly those with substitution in the 4-position. A subset of the most active compounds was further evaluated for adverse cardiovascular effects in the anesthetized rat model. In addition to excellent binding at the alpha (2D) adrenoceptor, the 4-bromo analogues 20e and 21e were very active in the rat abdominal irritant test (RAIT) with ED50 doses of 0.38 and 0.31 mg/kg, respectively. We constructed a pharmacophore model based on the biological activity of the present series, dexmedetomidine (1), and conformationally restrained analogues 3 and 4.

  DOI：

  10.1021/jm0003891
• 作为产物：
  描述：

  3,4-二甲基-2-噻吩甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 3,4-Dimethyl-thiophene-2-carboxylic acid methoxy-methyl-amide
  参考文献：
  名称：

  α₂ Adrenoceptor Agonists as Potential Analgesic Agents. 3. Imidazolylmethylthiophenes

  摘要：

  A series of imidazolylmethylthiophenes has been prepared and evaluated as ligands for the at adrenoceptor. These compounds were tested in two animal models that are predictive of analgesic activity in humans. The 3-thienyl compounds were generally the most potent, particularly those with substitution in the 4-position. A subset of the most active compounds was further evaluated for adverse cardiovascular effects in the anesthetized rat model. In addition to excellent binding at the alpha (2D) adrenoceptor, the 4-bromo analogues 20e and 21e were very active in the rat abdominal irritant test (RAIT) with ED50 doses of 0.38 and 0.31 mg/kg, respectively. We constructed a pharmacophore model based on the biological activity of the present series, dexmedetomidine (1), and conformationally restrained analogues 3 and 4.

  DOI：

  10.1021/jm0003891

文献信息

• α₂ Adrenoceptor Agonists as Potential Analgesic Agents. 3. Imidazolylmethylthiophenes
  作者：Robert E. Boyd、C. Royce Rasmussen、Jeffery B. Press、Robert B. Raffa、Ellen E. Codd、Charlene D. Connelly、Quan S. Li、Rebecca P. Martinez、Martin A. Lewis、Harold R. Almond、Allen B. Reitz

  DOI：10.1021/jm0003891

  日期：2001.3.1

  A series of imidazolylmethylthiophenes has been prepared and evaluated as ligands for the at adrenoceptor. These compounds were tested in two animal models that are predictive of analgesic activity in humans. The 3-thienyl compounds were generally the most potent, particularly those with substitution in the 4-position. A subset of the most active compounds was further evaluated for adverse cardiovascular effects in the anesthetized rat model. In addition to excellent binding at the alpha (2D) adrenoceptor, the 4-bromo analogues 20e and 21e were very active in the rat abdominal irritant test (RAIT) with ED50 doses of 0.38 and 0.31 mg/kg, respectively. We constructed a pharmacophore model based on the biological activity of the present series, dexmedetomidine (1), and conformationally restrained analogues 3 and 4.