Benzofuran-2-yl-(3-benzyl-3,8-diaza-bicyclo[3.2.1]oct-8-yl)-methanone | 223593-83-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: Benzofuran-2-yl-(3-benzyl-3,8-diaza-bicyclo[3.2.1]oct-8-yl)-methanone
• CAS: 223593-83-7
• 化学式: C₂₂H₂₂N₂O₂
• 分子量: 346.429
• InChiKey: GXMYSGIIFABFIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  36.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Benzofuran-2-yl-(3-benzyl-3,8-diaza-bicyclo[3.2.1]oct-8-yl)-methanone 在 palladium on activated charcoal 氢气 、 红铝 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 1-[8-(1-Benzofuran-2-ylmethyl)-3,8-diazabicyclo[3.2.1]octan-3-yl]propan-1-one
  参考文献：
  名称：

  Benzocondensed derivatives as rigid analogues of the μ-opioid agonist 3(8)-cinnamyl-8(3)-propionyl-3,8-diazabicyclo[3.2.1]octanes: synthesis, modeling, and affinity

  摘要：

  A new series of rigid analogues (1a-g, 2a-g) of the previously reported analgesic 3-cinnamyl-8-propionyl-3,8-diazabicyclo[3.2.1]octane (I) and its reverted isomer 3-propionyl-8-cinnamyl (II) were synthesized, in which the cinnamyl substituent is incorporated in benzocondensed bicyclic systems. Binding assays for the affinity towards mu receptors indicated that, while in the reverted series 2 the beta-naphthylmethyl (2d) and the benzocycloheptenylmethyl derivative (2g) favorably compared with II, all compounds 1 displayed a mu-affinity lower than that of the parent I. Modeling studies suggest that the flexibility of the cinnamyl side chain plays an important role for activity. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00084-6
• 作为产物：
  描述：

  苯并呋喃-2-羧酸 在 氯化亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 Benzofuran-2-yl-(3-benzyl-3,8-diaza-bicyclo[3.2.1]oct-8-yl)-methanone
  参考文献：
  名称：

  Benzocondensed derivatives as rigid analogues of the μ-opioid agonist 3(8)-cinnamyl-8(3)-propionyl-3,8-diazabicyclo[3.2.1]octanes: synthesis, modeling, and affinity

  摘要：

  A new series of rigid analogues (1a-g, 2a-g) of the previously reported analgesic 3-cinnamyl-8-propionyl-3,8-diazabicyclo[3.2.1]octane (I) and its reverted isomer 3-propionyl-8-cinnamyl (II) were synthesized, in which the cinnamyl substituent is incorporated in benzocondensed bicyclic systems. Binding assays for the affinity towards mu receptors indicated that, while in the reverted series 2 the beta-naphthylmethyl (2d) and the benzocycloheptenylmethyl derivative (2g) favorably compared with II, all compounds 1 displayed a mu-affinity lower than that of the parent I. Modeling studies suggest that the flexibility of the cinnamyl side chain plays an important role for activity. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00084-6