7'-{3,4-bis[2-(1,3-dioxolanyl)]-benzoylamino}-3-{3,4-bis[2-(1,3-dioxolanyl)]-benzyloxy}-17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-14-hydroxyindolo[2',3':6,7]-morphinan | 336129-82-9

• 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: 7'-{3,4-bis[2-(1,3-dioxolanyl)]-benzoylamino}-3-{3,4-bis[2-(1,3-dioxolanyl)]-benzyloxy}-17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-14-hydroxyindolo[2',3':6,7]-morphinan
• 英文别名: [(1S,2S,13R,21R)-9-[[3,4-bis(1,3-dioxolan-2-yl)benzoyl]amino]-22-(cyclopropylmethyl)-2-hydroxy-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-16-yl] 3,4-bis(1,3-dioxolan-2-yl)benzoate
• CAS: 336129-82-9
• 化学式: C₅₂H₅₁N₃O₁₃
• 分子量: 925.989
• InChiKey: PZQNPEKDDNFVAE-BXFQOJHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  68
• 可旋转键数：
  11
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  178
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  7'-{3,4-bis[2-(1,3-dioxolanyl)]-benzoylamino}-3-{3,4-bis[2-(1,3-dioxolanyl)]-benzyloxy}-17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-14-hydroxyindolo[2',3':6,7]-morphinan 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以48%的产率得到7'-{3,4-bis[2-(1,3-dioxolanyl)]-benzoylamino}-17-(cyclopropylmethyl)-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：

  3,4-双(二溴甲基)苯甲酸 在 sodium carbonate 、 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 N,N-二甲基甲酰胺 为溶剂， 反应 122.5h， 生成 7'-{3,4-bis[2-(1,3-dioxolanyl)]-benzoylamino}-3-{3,4-bis[2-(1,3-dioxolanyl)]-benzyloxy}-17-(cyclopropylmethyl)-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

文献信息

• Covalently Induced Activation of the δ Opioid Receptor by a Fluorogenic Affinity Label, 7‘-(Phthalaldehydecarboxamido)naltrindole (PNTI)
  作者：Bertrand Le Bourdonnec、Rachid El Kouhen、Gennady Poda、Ping Y. Law、Horace H. Loh、David M. Ferguson、Philip S. Portoghese

  DOI：10.1021/jm010004u

  日期：2001.3.1
• <i>o</i>-Naphthalenedicarboxaldehyde Derivative of 7‘-Aminonaltrindole as a Selective δ-Opioid Receptor Affinity Label
  作者：Sarika Prabhu Haris、Yan Zhang、Bertrand Le Bourdonnec、Christopher R. McCurdy、Philip S. Portoghese

  DOI：10.1021/jm061194h

  日期：2007.7.1

  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.