6-甲酰基-2-萘腈 | 56358-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 6-甲酰基-2-萘腈
• 英文名称: 6-cyano-2-naphthaldehyde
• 英文别名: 6-formyl-2-naphthonitrile；6-Cyanonaphthaldehyd-(2)；6-cyano-2-naphthalenecarbaldehyde；6-formylnaphthalene-2-carbonitrile
• CAS: 56358-62-4
• 化学式: C₁₂H₇NO
• 分子量: 181.194
• InChiKey: WKUDIPHFBLCTFN-UHFFFAOYSA-N

物化性质

• 熔点：
  173-175 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  382.5±15.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-甲酰基-2-萘腈 在 盐酸 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 生成
  参考文献：
  名称：

  Substrate profiling of Finegoldia magna SufA protease, inhibitor screening and application to prevent human fibrinogen degradation and bacteria growth in vitro

  摘要：

  SufA, which belongs to the subtilisin-like serine protease family, contains a non-canonical Asp-His-Ser catalytic triad. Under in vitro conditions, SufA is capable of human fibrinogen hydrolysis leading to inhibition of fibrin network formation, thus suggesting its important role in the development and progression of Finegoldia magna infections. In addition, it has been demonstrated that SufA can hydrolyze antibacterial peptides such as LL-37 and the chemokine MIG/CXCL 9, hence evading host defence mechanisms. Although the SufA protease from E magna was discovered several years ago, its optimal substrate preference has not yet been identified. Considering the role of SufA, we have focused on the profiling of its substrate sequence preference spanning S1-S3 binding pockets using the FRET (fluorescence resonance energy transfer) approach. Next, based on the structure of the P1 residue of the developed substrate, we narrowed the inhibitor screening to the phosphonic analogues of amino acids containing an arginine-like side chain. Among all the compounds tested, only Cbz-6-AmNphth(P)(OPh)(2) showed any inhibitory activity against SufA displaying k(2)/K-i value of 10 800 M-1 s(-1). In addition, it prevented SufA-mediated human fibrinogen hydrolysis in vitro and exhibited potent antibacterial activity against E magna, Staphylococcus aureus and Escherichia coli.Herein, we report on the substrate specificity, synthesis and kinetic evaluation of phosphonic inhibitors of SufA protease from E magna which could help to establish its function in pathogenesis development and may lead to the elaboration of new antibacterial drugs. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biochi.2014.05.006
• 作为产物：
  描述：

  2,6-萘二羧酸二甲酯 在 吡啶 、 锂硼氢 、 氯化亚砜 、 草酰氯 、 氨 、 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 6-甲酰基-2-萘腈
  参考文献：
  名称：

  Substrate profiling of Finegoldia magna SufA protease, inhibitor screening and application to prevent human fibrinogen degradation and bacteria growth in vitro

  摘要：

  SufA, which belongs to the subtilisin-like serine protease family, contains a non-canonical Asp-His-Ser catalytic triad. Under in vitro conditions, SufA is capable of human fibrinogen hydrolysis leading to inhibition of fibrin network formation, thus suggesting its important role in the development and progression of Finegoldia magna infections. In addition, it has been demonstrated that SufA can hydrolyze antibacterial peptides such as LL-37 and the chemokine MIG/CXCL 9, hence evading host defence mechanisms. Although the SufA protease from E magna was discovered several years ago, its optimal substrate preference has not yet been identified. Considering the role of SufA, we have focused on the profiling of its substrate sequence preference spanning S1-S3 binding pockets using the FRET (fluorescence resonance energy transfer) approach. Next, based on the structure of the P1 residue of the developed substrate, we narrowed the inhibitor screening to the phosphonic analogues of amino acids containing an arginine-like side chain. Among all the compounds tested, only Cbz-6-AmNphth(P)(OPh)(2) showed any inhibitory activity against SufA displaying k(2)/K-i value of 10 800 M-1 s(-1). In addition, it prevented SufA-mediated human fibrinogen hydrolysis in vitro and exhibited potent antibacterial activity against E magna, Staphylococcus aureus and Escherichia coli.Herein, we report on the substrate specificity, synthesis and kinetic evaluation of phosphonic inhibitors of SufA protease from E magna which could help to establish its function in pathogenesis development and may lead to the elaboration of new antibacterial drugs. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biochi.2014.05.006

文献信息

• Novel ligands for the hisb10 zn2+ sites of the r-state insulin hexamer
  申请人：——

  公开号：US20030229120A1

  公开（公告）日：2003-12-11

  Novel ligands for the HisB10 Zn 2+ sites of the R-state insulin hexamer that are capable of prolonging the action of insulin preparations are disclosed.

  揭示了能够延长胰岛素制剂作用的R-态胰岛素六聚体的HisB10 Zn2+位点的新配体。
• [EN] PHAMACEUTICAL PREPARATIONS COMPRISING INSULIN<br/>[FR] PREPARATIONS PHARMACEUTIQUES CONTENANT DE L'INSULINE
  申请人：NOVO NORDISK AS

  公开号：WO2006005683A1

  公开（公告）日：2006-01-19

  Novel preparations comprising ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer wherein the ligand is extended by protamine that are capable of prolonging the ac­tion of insulin preparations.

  新型制剂包括配体，用于R-态胰岛素六聚体的HisB10 Zn2+位点，其中配体通过精氨酸延长，能够延长胰岛素制剂的作用。
• Stabilised insulin compositions
  申请人：Kaarsholm Christian Niels

  公开号：US20050065066A1

  公开（公告）日：2005-03-24

  The present invention provides pharmaceutical compositions comprising insulin and novel ligands for the His B10 Zn 2+ sites of the R-state insulin hexamer. The resulting preparations have improved physical and chemical stability.

  本发明提供了包含胰岛素和新型配体的药物组合物，用于R-态胰岛素六聚体的His B10 Zn2+位点。由此制备的药物具有改善的物理和化学稳定性。
• [EN] PHARMACEUTICAL PREPARATIONS COMPRISING ACID-STABILISED INSULIN<br/>[FR] PREPARATIONS PHARMACEUTIQUES CONTENANT DE L'INSULINE STABILISEE D'UN POINT DE VUE ACIDE
  申请人：NOVO NORDISK AS

  公开号：WO2004080480A1

  公开（公告）日：2004-09-23

  Novel ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer that are capable of prolonging the action of insulin preparations are disclosed.

  揭示了能够延长胰岛素制剂作用的R态胰岛素六聚体的HisB10 Zn2+位点的新配体。
• Preparation and Pharmacological Evaluation of Novel Glycoprotein (Gp) IIb/IIIa Antagonists. 1. The Selection of Naphthalene Derivatives.
  作者：Shin'ichiro ONO、Yoshihisa INOUE、Tomohiro YOSHIDA、Atsuyuki ASHIMORI、Keigo KOSAKA、Teruaki IMADA、Chikara FUKAYA、Norifumi NAKAMURA

  DOI：10.1248/cpb.47.1685

  日期：——

  The synthesis and design using molecular modeling techniques for non-peptide, low molecular weight novel fibrinogen receptor (glycoprotein IIb/IIIa: Gp IIb/IIIa) antagonists, is reported. We used a highly potent serine protease inhibitor, Nafamostat, having an amidinonaphthyl unit as the starting compound. The compounds 4-(6-amidino-2-naphthylaminocarbonyl)phenoxyacetic acid (5a) and 4-(6-amidino-

  报道了使用分子建模技术针对非肽，低分子量新型纤维蛋白原受体（糖蛋白IIb / IIIa：Gp IIb / IIIa）拮抗剂的合成和设计。我们使用了一种高效的丝氨酸蛋白酶抑制剂，Nafamostat，其具有ona基萘基单元作为起始化合物。化合物4-（6-ami基-2-萘氨基羰基）苯氧基乙酸（5a）和4-（6-ami基-2-萘甲酰胺基）苯氧基乙酸（5b）抑制5'-二磷酸腺苷（ADP）诱导的人聚集。富含血小板的血浆（PRP）的IC50值分别为0.05和0.07 microM，并且失去了抑制多种丝氨酸蛋白酶（包括凝血酶，Xa因子，纤溶酶和胰蛋白酶）的能力。