(E)-N′-benzylidene-3-hydroxy-2-naphthohydrazide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-N′-benzylidene-3-hydroxy-2-naphthohydrazide
• 英文别名: (E)-N'-benzylidene-3-hydroxy-2-naphthohydrazide；(E)-N′-benzylidene-3-hydroxynaphthalene-2-carbohydrazide；3-hydroxy-2-naphthoyl hydrazone of benzaldehyde；3-hydroxy-N'-[(E)-phenylmethylidene]naphthalene-2-carbohydrazide；N-[(E)-benzylideneamino]-3-hydroxynaphthalene-2-carboxamide
• 化学式: C₁₈H₁₄N₂O₂
• 分子量: 290.321
• InChiKey: BQTYCKJHLIHXHX-XDHOZWIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N′-benzylidene-3-hydroxy-2-naphthohydrazide 、 cobalt(II) acetate 以 甲醇 、 乙醇 为溶剂， 生成 Co(3-hydroxy-2-naphthoyl hydrazone of benzaldehyde)2
  参考文献：
  名称：

  Osman, M. M.; Ali, G. Y., Acta Chimica Academiae Scientiarum Hungaricae, 1981, vol. 108, # 1, p. 13 - 24

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羟基-3-萘甲酸 在 盐酸 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 6.25h， 生成 (E)-N′-benzylidene-3-hydroxy-2-naphthohydrazide
  参考文献：
  名称：

  Study of E/Z Isomerization in a Series of Novel Non-ligand Binding Pocket Androgen Receptor Antagonists

  摘要：

  We report the conformational analysis of a series of 3-hydroxy-N'-((naphthalen-2-yl)methylene)naphthalene-2-carbohydrazides. This class of compounds has recently been reported as androgen receptor (AR)-coactivator disruptors for potential application in prostate cancer therapy. Definition of the E/Z isomerism around the imine linker group (hydrazide) is significant from a mechanistic point of view. A detailed study using theoretical calculations coupled with experimental techniques has allowed us determine an initial preference for the E isomer. The biological activity of newly synthesized compounds at the androgen receptor, along with a series of structural analogs, was determined and provides the basis for preliminary qualitative structure-activity relationship analysis.

  DOI：

  10.1021/ci300299n

文献信息

• Crystallographic Elucidation of Stimuli-Controlled Molecular Rotation for a Reversible Sol–Gel Transformation
  作者：Mehebub Ali Khan、Soumen Ghosh、Sachinath Bera、Anamika Hoque、Ismail Sk、Shagufi Naz Ansari、Shaikh M. Mobin、Md. Akhtarul Alam

  DOI：10.1021/acs.joc.9b02944

  日期：2020.3.20

  get an idea about the most probable microporous supramolecular environment in the gel state, gelator molecule 1 has been crystallized from its gelling solvent (dimethylformamide). Crystal structure analysis of 1 shows a strong π···π stacking interaction between the electron-deficient pentafluorophenyl ring and electron-rich naphthyl ring. The gelling solvent situated in the "molecular pocket" stitches

  为了了解凝胶状态下最可能的微孔超分子环境，已将凝胶剂分子1从其胶凝溶剂（二甲基甲酰胺）中结晶出来。1的晶体结构分析显示，缺电子的五氟苯基环与富电子的萘基环之间有很强的π···π堆积相互作用。位于“分子袋”中的胶凝溶剂通过弱的氢键相互作用缝合胶凝剂，以促进有机凝胶的形成。扫描电子显微镜分析显示出类似带状的纤维形态，其结晶态类似于1的超分子排列，如粉末X射线衍射所示。在外部刺激（氟化四丁基铵）存在下，1的有机凝胶分解成溶胶。已经基于X射线单晶分析解释了这种溶胶-凝胶转变现象。从溶胶态获得的单晶显示1的萘基-OH去质子化，导致CC键旋转，这在溶胶-凝胶转化中起主要作用。胶凝剂1在凝胶状态下显示弱的绿色荧光，而在溶胶状态下显示高强度的黄色荧光。此外，已经观察到分别在酸和氟离子的存在下与光谱性质的变化相关的可逆的溶胶-凝胶转变。胶凝剂1在凝胶状态下显示弱的绿色荧光，而在溶胶状态下显示高强度的黄色荧光
• RUBBER COMPOSITION AND PNEUMATIC TIRES
  申请人：Bridgestone Corporation

  公开号：EP0909788A1

  公开（公告）日：1999-04-21

  A rubber composition prepared by compounding 0.05 to 20 parts by weight of at least one selected from substituted hydrazide compounds represented by the following Formulas (I) to (IV) per 100 parts by weight of a rubber component comprising at least one rubber selected from the group consisting of natural rubber and synthetic rubber, and a pneumatic tire using the same: wherein A represents one selected from the group consisting of an aromatic group which may have a substituent, a hydantoin ring which may have a substituent, and a saturated or unsaturated linear hydrocarbon having 1 to 18 carbon atoms; Y represents hydrogen, an amino group, an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group, an alkenyl group, an aromatic group, a pyridyl group or hydrazino group; and R1 to R11 each represent hydrogen, an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group or an aromatic group.

  一种橡胶组合物，其制备方法是每 100 重量份由至少一种选自天然橡胶和合成橡胶组的橡胶组成的橡胶组分中混入 0.05 至 20 重量份的至少一种选自下式(I)至(IV)所代表的取代酰肼化合物，以及使用该组合物的充气轮胎： 其中 A 代表选自芳香基团（可具有取代基）、海因环（可具有取代基）和具有 1 至 18 个碳原子的饱和或不饱和线性烃；Y 代表氢、氨基、具有 1 至 18 个碳原子的烷基、环烷基、烯基、芳香基、吡啶基或肼基；R1 至 R11 分别代表氢、具有 1 至 18 个碳原子的烷基、环烷基或芳香基。
• Rubber composition and pneumatic tire
  申请人：Bridgestone Corporation

  公开号：EP1420044A2

  公开（公告）日：2004-05-19

  A hydrazone derivative represented by Formula (V):         ZC(=O)NHN=C(CH3) (CH2CH(CH3)2)     (V) wherein Z represents 3-hydroxy-2-naphthyl, 1-hydroxy-2-naphthyl, 2-hydroxyphenyl or 2,6-dihydroxyphenyl group.

  式 (V) 所代表的腙衍生物： ZC(=O)NHN=C(CH3) (CH2CH( )2) (V) 其中 Z 代表 3-羟基-2-萘基、1-羟基-2-萘基、2-羟基苯基或 2,6-二羟基苯基。
• ANTIRUST COMPOSITION
  申请人：Otsuka Chemical Co., Ltd.

  公开号：EP1717350A1

  公开（公告）日：2006-11-02

  A rust preventive agent which contains, as an active component, at least one species selected from a compound of the formula (1) or (2) and a salt thereof; a rust preventing method and a rust preventive resin composition using the rust preventive agent.

  一种防锈剂，其中含有至少一种从式（1）或（2）化合物及其盐中选出的活性成分；一种防锈方法和一种使用该防锈剂的防锈树脂组合物。
• Structure–Activity Relationships in Non-Ligand Binding Pocket (Non-LBP) Diarylhydrazide Antiandrogens
  作者：Laura Caboni、Billy Egan、Brendan Kelly、Fernando Blanco、Darren Fayne、Mary J. Meegan、David G. Lloyd

  DOI：10.1021/ci400189m

  日期：2013.8.26

  We report the synthesis and a study of the structure activity relationships of a new series of diarylhydrazides as potential selective non-ligand binding pocket androgen receptor antagonists. Their biological activity as antiandrogens in the context of the development of treatments for castration resistant prostate cancer was evaluated using in vitro time resolved fluorescence resonance energy transfer and fluorescence polarization on target assays. Additionally, a theoretical study combining docking and molecular dynamics methods was performed to provide insight into their mechanism of action as a basis for further lead optimization studies.