benzofuran-2-yl(piperazin-1-yl)methanone hydrochloride | 1239983-17-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: benzofuran-2-yl(piperazin-1-yl)methanone hydrochloride
• 英文别名: 1-(1-Benzofuran-2-carbonyl)piperazinehydrochloride；1-benzofuran-2-yl(piperazin-1-yl)methanone;hydrochloride
• CAS: 1239983-17-5
• 化学式: C₁₃H₁₄N₂O₂*ClH
• 分子量: 266.727
• InChiKey: QHGNOZGVPDXNHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  45.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  tert-butyl 4-(2-benzofuranoyl)piperazine-1-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以100%的产率得到benzofuran-2-yl(piperazin-1-yl)methanone hydrochloride
  参考文献：
  名称：

  Design, Synthesis, and Structure−Affinity Relationships of Regioisomeric N-Benzyl Alkyl Ether Piperazine Derivatives as σ-1 Receptor Ligands

  摘要：

  A series of N-(benzofuran-2-ylmethyl)-N'-benzylpiperazines bearing alkyl or fluoroalkyl aryl ethers were synthesized and evaluated at various central nervous system receptors. Examination of in vitro sigma(1) {[H-3](+)-pentazocinel and sigma(2) ([H-3]DTG) receptor binding profiles of piperazines 11-13 and 25-36 revealed several highly potent and sigma(1) selective ligands, notably, N-(benzofuran-2-ylmethyl)-N'-(4'-methoxybenzyl)piperazine (13, K-i = 2.7 nM, sigma(2)/sigma(1) = 38) and N-(benzofuran-2-ylmethyl)-N'-(4'-(2 ''-fluoroethoxy)benzyl)piperazine (30, K-i = 2.6 nM, sigma(2)/sigma(1) = 187). Structural features for optimal sigma(1) receptor affinity and selectivity over the 07 receptor were identified. On the basis of its favorable log D value, 13 was selected as a candidate for the development of a sigma(1) receptor positron emission tomography radiotracer. [C-11]13 showed high uptake in the brain and other a receptor-rich organs of a Papio hamadryas baboon. The in vivo evaluation of [C-11]13 indicates that this radiotracer is a suitable candidate for imaging the sigma(1) receptor in neurodegenerative processes.

  DOI：

  10.1021/jm100639f