N-[(4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]-1,3-dimethoxy-1,3-dihydrobenzo[f][2]benzofuran-6-carboxamide | 446242-04-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N-[(4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]-1,3-dimethoxy-1,3-dihydrobenzo[f][2]benzofuran-6-carboxamide
• CAS: 446242-04-2
• 化学式: C₃₅H₃₈N₂O₇
• 分子量: 598.696
• InChiKey: WYUVROYJCSTMTK-FXEYISCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  44
• 可旋转键数：
  6
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-[(4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]-1,3-dimethoxy-1,3-dihydrobenzo[f][2]benzofuran-6-carboxamide 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 120.0h， 以55%的产率得到[(4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]-(6,7-diformylnaphthalene-2-carbonyl)azanium;chloride
  参考文献：
  名称：

  Naphthalene Dicarboxaldehyde as an Electrophilic Fluorogenic Moiety for Affinity Labeling:  Application to Opioid Receptor Affinity Labels with Greatly Improved Fluorogenic Properties

  摘要：

  To develop ligands with fluorogenic properties amenable for following the kinetics of cross-linking to receptors, a naphthalene dicarboxaldehyde moiety has been attached to an opiate pharmacophore 2 and evaluated in mu opioid receptors. The fluorescence of the benzo[f]isoindole formed upon cross-linking of mu opioid receptors by 2 permitted the time-course of covalent bonding to be followed. This demonstrated proof-of-concept suggests the usefulness of naphthalene dicarboxaldehyde-containing affinity labels as kinetic probes.

  DOI：

  10.1021/jm015586u
• 作为产物：
  描述：

  6,7-diformylnaphthalene-2-carboxylic acid 在 lithium hydroxide 、 1-羟基苯并三唑 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 N-[(4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]-1,3-dimethoxy-1,3-dihydrobenzo[f][2]benzofuran-6-carboxamide
  参考文献：
  名称：

  Naphthalene Dicarboxaldehyde as an Electrophilic Fluorogenic Moiety for Affinity Labeling:  Application to Opioid Receptor Affinity Labels with Greatly Improved Fluorogenic Properties

  摘要：

  To develop ligands with fluorogenic properties amenable for following the kinetics of cross-linking to receptors, a naphthalene dicarboxaldehyde moiety has been attached to an opiate pharmacophore 2 and evaluated in mu opioid receptors. The fluorescence of the benzo[f]isoindole formed upon cross-linking of mu opioid receptors by 2 permitted the time-course of covalent bonding to be followed. This demonstrated proof-of-concept suggests the usefulness of naphthalene dicarboxaldehyde-containing affinity labels as kinetic probes.

  DOI：

  10.1021/jm015586u