N-[(1S,2S,13R,21R)-22-(cyclopropylmethyl)-2,16-dihydroxy-14-oxa-11,22-diazaheptacyclo[13.9.1.01,13.02,21.04,12.05,10.019,25]pentacosa-4(12),5(10),6,8,15,17,19(25)-heptaen-9-yl]-1,3-dimethoxy-1,3-dihydrobenzo[f][2]benzofuran-6-carboxamide | 943600-48-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: N-[(1S,2S,13R,21R)-22-(cyclopropylmethyl)-2,16-dihydroxy-14-oxa-11,22-diazaheptacyclo[13.9.1.01,13.02,21.04,12.05,10.019,25]pentacosa-4(12),5(10),6,8,15,17,19(25)-heptaen-9-yl]-1,3-dimethoxy-1,3-dihydrobenzo[f][2]benzofuran-6-carboxamide
• CAS: 943600-48-4
• 化学式: C₄₁H₃₉N₃O₇
• 分子量: 685.777
• InChiKey: SVVBOANWVWCNQD-UUYIJUIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  51
• 可旋转键数：
  6
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-[(1S,2S,13R,21R)-22-(cyclopropylmethyl)-2,16-dihydroxy-14-oxa-11,22-diazaheptacyclo[13.9.1.01,13.02,21.04,12.05,10.019,25]pentacosa-4(12),5(10),6,8,15,17,19(25)-heptaen-9-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 72.0h， 以0.035 g的产率得到17-(cyclopropylmethyl)-7'-(3,4-diformylnaphthoylamino)-6,7-didehydro-4,5α-epoxy-14-hydroxyindolo[2',3':6,7]-morphinan
  参考文献：
  名称：

  o-Naphthalenedicarboxaldehyde Derivative of 7‘-Aminonaltrindole as a Selective δ-Opioid Receptor Affinity Label

  摘要：

  Incorporation of a naphthalene-dialdehyde moiety into the delta antagonist, 6'-aminonaltrindole afforded a potent, selective, irreversible delta-agonist 1. However, flow cytometry studies revealed no time-dependent specific fluorescence, suggesting that both Lys214 and Cys216 at the recognition site are not involved in covalent binding. Molecular simulation studies suggest that compound 1 may form a Schiff base with the epsilon-amino group of Lys214, which could explain its irreversibility and transformation into a delta-agonist through a conformational change of TM5.

  DOI：

  10.1021/jm061194h
• 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 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 97.0h， 生成 N-[(1S,2S,13R,21R)-22-(cyclopropylmethyl)-2,16-dihydroxy-14-oxa-11,22-diazaheptacyclo[13.9.1.01,13.02,21.04,12.05,10.019,25]pentacosa-4(12),5(10),6,8,15,17,19(25)-heptaen-9-yl]-1,3-dimethoxy-1,3-dihydrobenzo[f][2]benzofuran-6-carboxamide
  参考文献：
  名称：

  o-Naphthalenedicarboxaldehyde Derivative of 7‘-Aminonaltrindole as a Selective δ-Opioid Receptor Affinity Label

  摘要：

  Incorporation of a naphthalene-dialdehyde moiety into the delta antagonist, 6'-aminonaltrindole afforded a potent, selective, irreversible delta-agonist 1. However, flow cytometry studies revealed no time-dependent specific fluorescence, suggesting that both Lys214 and Cys216 at the recognition site are not involved in covalent binding. Molecular simulation studies suggest that compound 1 may form a Schiff base with the epsilon-amino group of Lys214, which could explain its irreversibility and transformation into a delta-agonist through a conformational change of TM5.

  DOI：

  10.1021/jm061194h