4-hydroxy-3-methoxy-benzoic acid-(4-methoxy-benzylidenehydrazide)

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-hydroxy-3-methoxy-benzoic acid-(4-methoxy-benzylidenehydrazide)
• 英文别名: 4-Hydroxy-3-methoxy-benzoesaeure-(4-methoxy-benzylidenhydrazid)；4-Methoxy-benzaldehyd-vanilloylhydrazon；4-Hydroxy-3-methoxy-benzoic acid (4-methoxy-benzylidene)-hydrazide；4-hydroxy-3-methoxy-N-[(E)-(4-methoxyphenyl)methylideneamino]benzamide
• 化学式: C₁₆H₁₆N₂O₄
• 分子量: 300.314
• InChiKey: FOLCMUGNDQVRGT-LICLKQGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  80.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  香草酸 在 硫酸 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 4-hydroxy-3-methoxy-benzoic acid-(4-methoxy-benzylidenehydrazide)
  参考文献：
  名称：

  Design, synthesis and antibacterial activities of vanillic acylhydrazone derivatives as potential β-ketoacyl-acyl carrier protein synthase III (FabH) inhibitors

  摘要：

  Fatty acid biosynthesis is essential for bacterial survival. FabH, beta-ketoacyl-acyl carrier protein (ACP) synthase III, is a particularly attractive target, since it is central to the initiation of fatty acid biosynthesis and is highly conserved among Gram-positive and Gram-negative bacteria. A series of acylhydrazone derivatives were synthesized and developed as potent inhibitors of FabH. This inhibitor class demonstrates strong broad-spectrum antibacterial activity. Compounds with potent antibacterial activities were tested for their Escherichia coli FabH inhibitory activity. Especially, compound E9 showed the most potent antibacterial activity with MIC values of 0.39-1.56 mu g/mL against the tested bacterial strains and exhibited the most potent E. coli FabH inhibitory activity with IC50 of 2.5 mu M. Docking simulation was performed to position compound E9 into the E. coli FabH active site to determine the probable binding conformation. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.009

文献信息

• Identification of Alkylidene Hydrazides as Glucagon Receptor Antagonists
  作者：Anthony Ling、Yufeng Hong、Javier Gonzalez、Vlad Gregor、Alex Polinsky、Atsuo Kuki、Shenghua Shi、Kimberly Teston、Douglas Murphy、John Porter、Dan Kiel、James Lakis、Kenna Anderes、John May、Lotte Bjerre Knudsen、Jesper Lau

  DOI：10.1021/jm000547o

  日期：2001.9.1

  High throughput screening of our small molecule combinatorial library identified a class of benzoylnaphthalenehydrazones with modest affinity for the human glucagon receptor. Optimization of this initial hit through a series of targeted libraries and traditional medicinal chemistry led to ligands with nanomolar affinities. Pharmacological evaluation demonstrated that these ligands were competitive glucagon receptor antagonists. Intravenous administration of a representative benzoylnaphthalenehydrazone into rats attenuated glucagon-stimulated glucose levels.