2-(((2-hydroxynaphthalen-1-yl)methylene)amino)benzonitrile | 77761-39-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(((2-hydroxynaphthalen-1-yl)methylene)amino)benzonitrile
• 英文别名: 1-<(2'-cyanophenylimino)methyl>-2-naphthol；1-[(2'-cyanophenylimino)methyl]-2-naphthol
• CAS: 77761-39-8
• 化学式: C₁₈H₁₂N₂O
• 分子量: 272.306
• InChiKey: YUIYFCPUVIASRH-UDWIEESQSA-N

物化性质

• 沸点：
  544.8±35.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.38
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-羟基-1-萘甲醛 、 2-氨基苯甲腈 以 乙醇 为溶剂， 反应 0.33h， 生成 2-(((2-hydroxynaphthalen-1-yl)methylene)amino)benzonitrile
  参考文献：
  名称：

  螯合研究。第9部分。1-[[（取代的苯基）偶氮] -2-萘酚和1-[（取代的苯基亚氨基）甲基] -2-萘酚配体的钴配合物。互变异构和反应性

  摘要：

  光谱表征（1 H和13 C NMR，IR，拉曼光谱，和UV-可见光）的各种1 - [（取代的苯基）偶氮] -2-萘酚，R-哈兹（R = 4'--ME，4'- OMe，4'-Cl，H，2'-OMe，2'-Me，2'-Cl和2'-Br）和1-[（取代的苯基亚氨基）甲基] -2-萘，R-Hsb（ R = 4'- OME，4'--ME，4'-氯，H，4'-BR，4'-CF 3，4'-CN，4'- NO 2，2'-OME，2'-ME ，2'-CHME 2，2'-氯，2'- CN，和2'-NO 2），在固体状态下和在极性和非极性溶剂中的溶液表明，氢键酮互变异构体在极性溶剂中占主导地位。钴（II）盐与R-Haz和R-Hsb在乙醇中反应生成[CoL 2 ]，顺式-[Co（HL）2 X 2 ]和fac- [CoL 3 ]（L ＝ R-az或R-sb）。这些配合物中的配体的互变异构形式是通过振动光谱法建立的，在[Co（R-az）2

  DOI：

  10.1039/dt9810000559

文献信息

• Studies of chelation. Part 9. Cobalt complexes of 1-[(substituted phenyl)azo]-2-naphthol and 1-[(substituted phenylimino)methyl]-2-naphthol ligands. Tautomerism and reactivity
  作者：Joseph A. Connor、David J. Fine、Raymond Price

  DOI：10.1039/dt9810000559

  日期：——

  naphthalene rings is a critical feature of the chelation process. The formation of [Co(R-az)3] from [Co(R-az)2] and from [Co(R-Haz)2X2] in the presence of air occurs easily and is acid catalysed. [Co(R-sb)3] is formed only under vigorously oxidising conditions. The isoelectronic ligands R-Haz and R-Hsb should not be regarded as identical in their reactivity towards cobalt(II).

  光谱表征（1 H和13 C NMR，IR，拉曼光谱，和UV-可见光）的各种1 - [（取代的苯基）偶氮] -2-萘酚，R-哈兹（R = 4'--ME，4'- OMe，4'-Cl，H，2'-OMe，2'-Me，2'-Cl和2'-Br）和1-[（取代的苯基亚氨基）甲基] -2-萘，R-Hsb（ R = 4'- OME，4'--ME，4'-氯，H，4'-BR，4'-CF 3，4'-CN，4'- NO 2，2'-OME，2'-ME ，2'-CHME 2，2'-氯，2'- CN，和2'-NO 2），在固体状态下和在极性和非极性溶剂中的溶液表明，氢键酮互变异构体在极性溶剂中占主导地位。钴（II）盐与R-Haz和R-Hsb在乙醇中反应生成[CoL 2 ]，顺式-[Co（HL）2 X 2 ]和fac- [CoL 3 ]（L ＝ R-az或R-sb）。这些配合物中的配体的互变异构形式是通过振动光谱法建立的，在[Co（R-az）2
• Sirtuin Inhibiting Compounds
  申请人：Sinclair David A

  公开号：US20090137681A1

  公开（公告）日：2009-05-28

  Provided herein are compositions and methods for treating or preventing cancer and autoimmune diseases. Compositions comprise a sirtuin inhibitory compound that decreases the activity of a sirtuin, such as SIRT1 or Sir2. Exemplary methods comprise contacting a cell or a molecule with a sirtuin inhibitory compound that decreases the activity of a sirtuin and thereby reduces the life span of a cell, kills the cell or renders it susceptible to certain cell stresses including radiation and chemotherapy. Other methods include treating pathogens expressing a sirtuin.

  本文提供了治疗或预防癌症和自身免疫疾病的组合物和方法。组合物包括抑制sirtuin的化合物，降低sirtuin的活性，如SIRT1或Sir2。示例方法包括将细胞或分子与抑制sirtuin的化合物接触，降低sirtuin的活性，从而缩短细胞的寿命，杀死细胞或使其对包括放射治疗和化疗在内的某些细胞应激变得敏感。其他方法包括治疗表达sirtuin的病原体。
• Design, Synthesis, and Biological Evaluation of Sirtinol Analogues as Class III Histone/Protein Deacetylase (Sirtuin) Inhibitors
  作者：Antonello Mai、Silvio Massa、Siva Lavu、Riccardo Pezzi、Silvia Simeoni、Rino Ragno、Francesca R. Mariotti、Francesco Chiani、Giorgio Camilloni、David A. Sinclair

  DOI：10.1021/jm050100l

  日期：2005.12.1

  In a search for potent inhibitors of class III histone/protein deacetylases (sirtuins), a series of sirtinol analogues have been synthesized and the degree of inhibition was assessed in vitro using recombinant yeast Sir2, human SIRT1, and human SIRT2 and in vivo with a yeast phenotypic assay. Two analogues, namely, 3- and 4-[(2-hydroxy-1-naphthalenylmethylene)amino] -N-(l-phenylethyl)benzamide (i.e., in- and p-sirtinol), were 2- to 10-fold more potent than sirtinol against human SIRT1 and SIRT2 enzymes. In yeast in vivo assay, these two small molecules were as potent as sirtinol. Compounds lacking the 2-hydroxy group at the naphthalene moiety or bearing several modifications at the benzene 2'-position of the aniline portion (carbethoxy, carboxy, and cyano) were 1.3-13 times less potent than sirtinol, whereas the 2'carboxamido analogue was totally inactive. Both (R)- and (S)-sirtinol had similar inhibitory effects on the yeast and human enzymes, demonstrating no enantioselective inhibitory effect.
• Solvent-Free Polymorphism Control in a Covalent Mechanochemical Reaction
  作者：Dominik Cinčić、Ivana Brekalo、Branko Kaitner

  DOI：10.1021/cg2013705

  日期：2012.1.4

  Four crystal modifications of a Schiff base derived from 2-hydroxy-1-naphthaldehyde and 2-aminobenzonitrile have been obtained by conventional solution-based methods. Three polymorphs out of four can be synthesized under solvent-free conditions. Herein we report simultaneous solvent-free covalent synthesis and polymorphism control of a single component system using mechanochemistry via neat grinding and seeding-assisted grinding, i.e. neat grinding in the presence of seed crystals. We describe the important role of seed crystals in directing the supramolecular organization of the product of covalent solvent-free reaction toward the intended polymorphic outcome. Single crystal X-ray analysis of the four crystal forms revealed conformational differences in molecules. Polymorphs display interesting and remarkably different molecular packing features via C-H center dot center dot center dot N and C-H center dot center dot center dot O interactions: 1D chains in form I, a 2D-network in forms III and IV, and a 3D-network in form II.