6-carboxymethyl-1,3-dimethoxybenzylnaphthalan | 446242-02-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 6-carboxymethyl-1,3-dimethoxybenzylnaphthalan
• 英文别名: Methyl 1,3-dimethoxy-1,3-dihydrobenzo[f][2]benzofuran-6-carboxylate
• CAS: 446242-02-0
• 化学式: C₁₆H₁₆O₅
• 分子量: 288.3
• InChiKey: PSTHBXFESGUJGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-carboxymethyl-1,3-dimethoxybenzylnaphthalan 在 盐酸 、 lithium hydroxide 、 1-羟基苯并三唑 、 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 、 丙酮 为溶剂， 反应 169.0h， 生成 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：

  甲醇 、 6,7-diformylnaphthalene-2-carboxylic acid 在 对甲苯磺酸 作用下， 以30%的产率得到6-carboxymethyl-1,3-dimethoxybenzylnaphthalan
  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

• Naphthalene Dicarboxaldehyde as an Electrophilic Fluorogenic Moiety for Affinity Labeling:  Application to Opioid Receptor Affinity Labels with Greatly Improved Fluorogenic Properties
  作者：Christopher R. McCurdy、Bertrand Le Bourdonnec、Thomas G. Metzger、Rachid El Kouhen、Yan Zhang、Ping Y. Law、Philip S. Portoghese

  DOI：10.1021/jm015586u

  日期：2002.7.1

  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.
• <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.