4-carboxybenzaldehyde phenylhydrazone | 61471-39-4

• 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-carboxybenzaldehyde phenylhydrazone
• 英文别名: 4-Formyl-benzoesaeure-phenylhydrazon；4-Carboxybenzaldehyd-phenylhydrazon；4-(phenylhydrazono-methyl)-benzoic acid；4-(Phenylhydrazono-methyl)-benzoesaeure；Terephthalaldehydsaeure-phenylhydrazon；4-((2-Phenylhydrazono)methyl)benzoic acid；4-[(phenylhydrazinylidene)methyl]benzoic acid
• CAS: 61471-39-4
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: HOISUZKVWWPRAA-UHFFFAOYSA-N

物化性质

• 熔点：
  221-222 °C
• 沸点：
  432.0±37.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• 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：
  4

反应信息

• 作为反应物：
  描述：

  4-carboxybenzaldehyde phenylhydrazone 在 potassium trimethylsilonate 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以83%的产率得到potassium hydrogen terephthalate
  参考文献：
  名称：

  三甲硅烷醇酸酯催化裂解Hy的有效方法氧化芳香醛

  摘要：

  芳香醛可被有效地氧化成相应的羧酸。该方案在一锅中涉及两个反应步骤。首先，通过与苯肼反应将醛转化为，然后用三甲基硅烷醇化物处理以产生羧酸。氧化既可以在溶液中也可以在固体载体上进行。

  DOI：

  10.1002/ejoc.201601238
• 作为产物：
  描述：

  对氰基氯苄 在 无水硝酸铜 、 溶剂黄146 作用下， 生成 4-carboxybenzaldehyde phenylhydrazone
  参考文献：
  名称：

  Reinglass, Chemische Berichte, 1891, vol. 24, p. 2422

  摘要：

  DOI：

文献信息

• Insights about resveratrol analogs against trypanothione reductase of <i>Leishmania braziliensis</i>: Molecular modeling, computational docking and <i>in vitro</i> antileishmanial studies
  作者：Adilson D. da Silva、Juliana A. dos Santos、Patrícia A. Machado、Lara A. Alves、Larissa C. Laque、Vinícius C. de Souza、Elaine S. Coimbra、Priscila V. S. Z. Capriles

  DOI：10.1080/07391102.2018.1502096

  日期：2019.7.24

  In this work, we combined molecular modeling, computational docking and in vitro analysis to explore the antileishmanial effect of some resveratrol analogs (ResAn), focusing on their pro-oxidant effect. The molecular target was the trypanothione reductase of Leishmania braziliensis (LbTryR), an essential component of the antioxidant defenses in trypanosomatid parasites. Three-dimensional structures

  在这项工作中，我们结合了分子建模，计算对接和体外分析，以研究某些白藜芦醇类似物（ResAn）的抗菊苣作用，重点是其促氧化剂作用。分子靶标是巴西利什曼原虫的锥虫硫磷还原酶（LbTryR），是锥虫的寄生虫中抗氧化剂防御的重要组成部分。对LbTryR的三维结构进行建模，ResAn1-5化合物的分子对接研究显示出以下亲和力：ResAn1> ResAn2> ResAn4> ResAn5> ResAn3。观察到这些化合物对LbTryR的亲和力与抗利什曼原虫的IC 50值呈正相关。（ResAn1
• Fast Hydrazone Reactants: Electronic and Acid/Base Effects Strongly Influence Rate at Biological pH
  作者：Eric T. Kool、Do-Hyoung Park、Pete Crisalli

  DOI：10.1021/ja407407h

  日期：2013.11.27

  Kinetics studies with structurally varied aldehydes and ketones in aqueous buffer at pH 7.4 reveal that carbonyl compounds with neighboring acid/base groups form hydrazones at accelerated rates. Similarly, tests of a hydrazine with a neighboring carboxylic acid group show that it also reacts at an accelerated rate. Rate constants for the fastest carbonyl/hydrazine combinations are 2-20 M-1 s(-1), which is faster than recent strain-promoted cycloaddition reactions.
• In vitro and in vivo anti-inflammatory properties of imine resveratrol analogues
  作者：Danielle Cristina Zimmermann-Franco、Bruna Esteves、Leticia Moroni Lacerda、Isabela de Oliveira Souza、Juliana Alves dos Santos、Nícolas de Castro Campos Pinto、Elita Scio、Adilson David da Silva、Gilson Costa Macedo

  DOI：10.1016/j.bmc.2018.08.029

  日期：2018.9

  Resveratrol is a natural polyphenol found mainly on red grapes and in red wine, pointed as an important antiinflammatory/immunomodulatory molecule. However, its bioavailability problems have limited its use encouraging the search for new alternatives agents. Thus, in this study, we synthesize 12 resveratrol analogues (6 imines, 1 thioimine and 5 hydrazones) and investigated its cytotoxicity, antioxidant activity and in vitro antiinflammatory/immunomodulatory properties. The most promising compounds were also evaluated in vivo. The results showed that imines presented less cytotoxicity, were more effective than resveratrol on DPPH scavenger and exhibited an anti-inflammatory profile. Among them, the imines with a radical in the para position, on the ring B, not engaged in an intramolecular hydrogen-interaction, showed more prominent anti-inflammatory activity modulating, in vivo, the edema formation, the inflammatory infiltration and cytokine levels. An immunomodulatory activity also was observed in these molecules. Thus, our results suggest that imines with these characteristics presents potential to control inflammatory disorders.
• Synthesis, and docking studies of arylhydrazone compounds and evaluation of their platelet aggregation inhibitory effect and cytotoxicity
  作者：Maryam H. Klidsar、Marjan Esfahanizadeh、Pantea Haghverdi、Salimeh Amidi、Farzad Kobarfard

  DOI：10.1007/s00044-022-02931-w

  日期：2022.9