3-acetylamino-4-(1(3)H-imidazol-4-yl)-butan-2-one | 70205-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-acetylamino-4-(1(3)H-imidazol-4-yl)-butan-2-one
• 英文别名: N-[1-(3H-Imidazol-4-YL)-3-oxo-butan-2-YL]acetamide；N-[1-(1H-imidazol-5-yl)-3-oxobutan-2-yl]acetamide
• CAS: 70205-45-7
• 化学式: C₉H₁₃N₃O₂
• 分子量: 195.221
• InChiKey: BTQSFAFDUGHODO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-acetylamino-4-(1(3)H-imidazol-4-yl)-butan-2-one 在 盐酸 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 3.5h， 生成 N-[1-(1H-imidazol-5-yl)-3-oxobutan-2-yl]propanamide
  参考文献：
  名称：

  α₂ Adrenoceptor Agonists as Potential Analgesic Agents. 1. (Imidazolylmethyl)oxazoles and -thiazoles

  摘要：

  A series of (imidazolylmethyl)oxazoles and -thiazoles were prepared and evaluated as alpha(2) adrenoceptor agonists. These compounds were also tested in in vivo paradigms that are predictive of analgesic activity. Variations in both the imidazole and thiazole portions of the molecule were investigated. Some of the more potent compounds such as 22, 26, 45, and 53 displayed at receptor binding in the 10-20 nM range and also had significant, antinociceptive activity in the mouse abdominal irritant test (MAIT).

  DOI：

  10.1021/jm990005a
• 作为产物：
  描述：

  乙酸酐 、 L-组氨酸 在 吡啶 作用下， 反应 2.0h， 以80%的产率得到3-acetylamino-4-(1(3)H-imidazol-4-yl)-butan-2-one
  参考文献：
  名称：

  Modulating the Serotonin Receptor Spectrum of Pulicatin Natural Products

  摘要：

  Serotonin (5-HT) receptors are important in health and disease, but the existence of 14 subtypes necessitates selective ligands. Previously, the pulicatins were identified as ligands that specifically bound to the subtype 5-HT2B in the 500 nM to 10 mu M range and that exhibited in vitro effects on cultured mouse neurons. Here, we examined the structure activity relationship of 30 synthetic and natural pulicatin derivatives using binding, receptor functionality, and in vivo assays. The results reveal the 2-arylthiazoline scaffold as a tunable serotonin receptor-targeting pharmacophore. Tests in mice show potential antiseizure and antinociceptive activities at high doses without motor impairment.

  DOI：

  10.1021/acs.jnatprod.7b00317

文献信息

• US8476240B2
  申请人：——

  公开号：US8476240B2

  公开（公告）日：2013-07-02