6,7-diformyl-2-naphthoic acid | 446242-03-1

• 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: 6,7-diformyl-2-naphthoic acid
• 英文别名: 1,3-dimethoxy-1,3-dihydronaphtho[2,3-c]furan-6-carboxylic acid；1,3-Dimethoxy-1,3-dihydrobenzo[f][2]benzofuran-6-carboxylic acid
• CAS: 446242-03-1
• 化学式: C₁₅H₁₄O₅
• 分子量: 274.273
• InChiKey: LBZXITQWIPLJNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,7-diformyl-2-naphthoic acid 在 盐酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 168.0h， 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：

  6,7-diformylnaphthalene-2-carboxylic acid 在 lithium hydroxide 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 生成 6,7-diformyl-2-naphthoic acid
  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

• Small molecule probes that target Ablkinase
  作者：Karunakaran A. Kalesh、Derek S. B. Sim、Jigang Wang、Kai Liu、Qingsong Lin、Shao Q. Yao

  DOI：10.1039/b919888a

  日期：——

  Two different strategies, namely a dialdehyde-based cross-linking and photo-affinity labeling, have been developed to generate small molecule activity-based probes (ABPs) for the Abelson (Abl) tyrosine kinase, of which probe 13, derived from the photo-affinity approach, showed specific labeling of Abl kinase present in a crude mammalian proteome.

  已经开发了两种不同的策略，即基于二醛的交联和光亲和标记，以生成针对Abelson（Abl）酪氨酸激酶的小分子基于活性的探针（ABP），其中探针13源自照片。 -亲和力方法显示了存在于哺乳动物粗蛋白质组中的Abl激酶的特异性标记。
• 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.