6,7-diformylnaphthalene-2-carboxylic acid | 446242-01-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6,7-diformylnaphthalene-2-carboxylic acid
• 英文别名: 6,7-diformyl-2-naphthoic acid
• CAS: 446242-01-9
• 化学式: C₁₃H₈O₄
• 分子量: 228.204
• InChiKey: VOQMSMSQAXHKHS-UHFFFAOYSA-N

物化性质

• 沸点：
  481.4±35.0 °C(Predicted)
• 密度：
  1.431±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,7-diformylnaphthalene-2-carboxylic acid 在 盐酸 、 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 、 丙酮 为溶剂， 反应 151.0h， 生成 [(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：

  2,5-二甲氧基四氢呋喃 、 3,4-diformylbenzoic acid 在 哌啶 、 溶剂黄146 作用下， 反应 18.0h， 以65%的产率得到6,7-diformylnaphthalene-2-carboxylic acid
  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

文献信息

• US7879929B2
  申请人：——

  公开号：US7879929B2

  公开（公告）日：2011-02-01
• <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.
• 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.