4-(1H-imidazol-1-ylmethyl)benzohydrazide | 139277-57-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(1H-imidazol-1-ylmethyl)benzohydrazide
• 英文别名: 4-[(1H-imidazol-1-yl)-methyl]benzhydrazide；Benzoic acid, 4-(1H-imidazol-1-ylmethyl)-, hydrazide；4-(imidazol-1-ylmethyl)benzohydrazide
• CAS: 139277-57-9
• 化学式: C₁₁H₁₂N₄O
• mdl: MFCD18263608
• 分子量: 216.242
• InChiKey: WKEIAFTVIMAIRV-UHFFFAOYSA-N

物化性质

• 熔点：
  154-155 °C(Solv: benzene (71-43-2); ethanol (64-17-5))
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(1H-imidazol-1-ylmethyl)benzohydrazide 在 碳酸氢钠 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 17.0h， 生成 2-[4-(1H-imidazol-1-ylmethyl)phenyl]-5-phenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis of 4-(1H-Azol-1-ylmethyl)benzohydrazides and Their Acyclic and Heterocyclic Derivatives

  摘要：

  4-(1H-吡唑-1-基甲基)苯并酰肼类化合物由甲基4-(溴甲基)苯甲酸酯、吡唑和肼水合物制备得到。4-(1H-咪唑-1-基甲基)苯并酰肼与羰基化合物反应生成脎，并研究了其互变异构现象。从这些酰肼出发，合成了1,3,4-噁二唑、1,2,4-三唑-5-硫酮和N-苯甲酰基-N′-烷基(芳基)磺酰基酰肼类化合物。

  DOI：

  10.1007/s11176-005-0180-7
• 作为产物：
  描述：

  4-(1H-咪唑-1-甲基)苯甲酸甲酯 在 一水合肼 作用下， 反应 4.0h， 以84%的产率得到4-(1H-imidazol-1-ylmethyl)benzohydrazide
  参考文献：
  名称：

  Synthesis of 4-(1H-Azol-1-ylmethyl)benzohydrazides and Their Acyclic and Heterocyclic Derivatives

  摘要：

  4-(1H-吡唑-1-基甲基)苯并酰肼类化合物由甲基4-(溴甲基)苯甲酸酯、吡唑和肼水合物制备得到。4-(1H-咪唑-1-基甲基)苯并酰肼与羰基化合物反应生成脎，并研究了其互变异构现象。从这些酰肼出发，合成了1,3,4-噁二唑、1,2,4-三唑-5-硫酮和N-苯甲酰基-N′-烷基(芳基)磺酰基酰肼类化合物。

  DOI：

  10.1007/s11176-005-0180-7

文献信息

• Aromatic hydrazides as specific inhibitors of bovine serum amine oxidase
  作者：M Artico、R Silvestri、G Stefancich、L Avigliano、A Di Giulio、M Maccarrone、E Agostinelli、B Mondovi、L Morpurgo

  DOI：10.1016/0223-5234(92)90005-l

  日期：1992.4

  New hydrazides were synthesized in search for specific inhibitors of bovine serum amine oxidase: a series of benzoic and phenylacetic acid hydrazides containing the 1H-imidazol-1-yl or the 1H-imidazol-1-ylmethyl group as (o, m, p)-substituent in the phenyl ring; an analogous series of p-substituted phenylhydrazides with 5 or 6-membered heterocyclic ring as substituent, and a series of similar phenylpropionic hydrazides. The longer and more flexible phenylacetic hydrazides, and to a somewhat lesser extent the phenylpropionic ones, were better specific inhibitors of bovine serum amine oxidase than the benzoic hydrazides, which were also bound by the enzyme with high affinity, but at a slow rate. Derivatives with p- and m -substituents were more reactive than the o-substituted ones. The chemical nature of the substituent was less important than its position in the phenyl ring and the presence of methylene spacers. These data point to the presence of a hydrophobic site at short distance from the protein carbonyl cofactor, so that simultaneous interaction of the 2 ends of the inhibitor molecule can occur at the 2 sites. The presence of the hydrophobic site was confirmed by the capability of some molecule deprived of the hydrazidic group to act as mild inhibitors. All hydrazides were less reactive by 2-3 orders of magnitude towards pig kidney diamine oxidase and FAD-dependent monoamine oxidase from rat brain mitochondria, while the other compounds showed similar inhibition power against all proteins. The specificity for the bovine enzyme seems therefore to be related to the concerted action of the 2 moieties of the inhibitor molecule.
• Synthesis of 4-(1H-Azol-1-ylmethyl)benzohydrazides and Their Acyclic and Heterocyclic Derivatives
  作者：V. A. Osyanin、P. P. Purygin、Z. P. Belousova

  DOI：10.1007/s11176-005-0180-7

  日期：2005.1

  4-(1H-Azol-1-ylmethyl)benzohydrazides were prepared from methyl 4-(bromomethyl)benzoate, azoles, and hydrazine hydrate. Reactions of 4-(1H-imidazol-1-ylmethyl)benzohydrazide with carbonyl compounds gave hydrazones whose tautomerism was studied. From the hydrazides, 1,3,4-oxadiazoles, 1,2,4-triazole- 5-thione, and N-benzoyl-N′-alkyl(aryl)sulfonylhydrazines were synthesized.

  4-(1H-吡唑-1-基甲基)苯并酰肼类化合物由甲基4-(溴甲基)苯甲酸酯、吡唑和肼水合物制备得到。4-(1H-咪唑-1-基甲基)苯并酰肼与羰基化合物反应生成脎，并研究了其互变异构现象。从这些酰肼出发，合成了1,3,4-噁二唑、1,2,4-三唑-5-硫酮和N-苯甲酰基-N′-烷基(芳基)磺酰基酰肼类化合物。