1-(2,4-dihydroxybenzylidene)-2-phenylhydrazine | 63452-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-(2,4-dihydroxybenzylidene)-2-phenylhydrazine
• 英文别名: 4-((2-phenylhydrazono)methyl)benzene-1,3-diol；2,4-dihydroxybenzaldehyde phenylhydrazone；2,4-dihydroxybenzylidene phenylhydrazone；2,4-dihydroxy-benzaldehyde phenylhydrazone；2,4-Dihydroxy-benzaldehyd-phenylhydrazon；Resorcylaldehyd-phenylhydrazon；4-[(phenylhydrazinylidene)methyl]benzene-1,3-diol
• CAS: 63452-52-8
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: ZNNMXRMLLZVIRS-UHFFFAOYSA-N

物化性质

• 熔点：
  159-161 °C(Solv: methanol (67-56-1))
• 沸点：
  437.7±28.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-fluorophenethyl)maleimide 、 1-(2,4-dihydroxybenzylidene)-2-phenylhydrazine 以 乙醇 为溶剂， 以7%的产率得到5-[1-(4-fluorophenylethyl)]-3-(2,4-dihydroxyphenyl)-1-phenyl-1,6a-dihydropyrrolo[3,4-c]pyrazole-4,6(3aH,5H)-dione
  参考文献：
  名称：

  吡咯酮类化合物及其制备方法和应用

  摘要：

  本发明公开了一种吡咯酮类化合物及其制备方法和应用，吡咯酮类化合物包括其对映异构体、非对映异构体、外消旋体和混合物，及其药学上可接受的盐或其溶剂合物或水合物，还公开了一种新型药物组合物，药物组合物包括治疗有效量的吡咯酮类化合物或其药学上可接受的盐和至少一种药学上可接受的载体的药物组合物。本发明公开的新型吡咯酮类化合物为未见文献报道全新化合物，是一类是具有开发前景的抗HIV‑1候选药物。

  公开号：

  CN105130995B
• 作为产物：
  描述：

  (2,4-dihydroxy-benzylidene)-dimethyl-ammonium; dichloro phosphate 以 乙醇 、 水 为溶剂， 反应 5.5h， 生成 1-(2,4-dihydroxybenzylidene)-2-phenylhydrazine
  参考文献：
  名称：

  2,4-dihydroxy benzaldehyde derived Schiff bases as small molecule Hsp90 inhibitors: Rational identification of a new anticancer lead

  摘要：

  Hsp90 is a molecular chaperone that heals diverse array of biomolecules ranging from multiple oncogenic proteins to the ones responsible for development of resistance to chemotherapeutic agents. Moreover they are over-expressed in cancer cells as a complex with co-chaperones and under-expressed in normal cells as a single free entity. Hence inhibitors of Hsp90 will be more effective and selective in destroying cancer cells with minimum chances of acquiring resistance to them. In continuation of our goal to rationally develop effective small molecule azomethines against Hsp90, we designed few more compounds belonging to the class of 2,4-dihydroxy benzaldehyde derived imines (1-13) with our validated docking protocol. The molecules exhibiting good docking score were synthesized and their structures were confirmed by IR, H-1 NMR and mass spectral analysis. Subsequently, they were evaluated for their potential to suppress Hsp90 ATPase activity by Malachite green assay. The antiproliferative effect of the molecules were examined on PC3 prostate cancer cell lines by adopting 3-(4,5-dimethythiazol-2yl)-2,5-diphenyl tetrazolium bromide (MTT) assay methodology. Finally, schiff base 13 emerged as the lead molecule for future design and development of Hsp90 inhibitors as anticancer agents. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.02.003

文献信息

• A short synthesis of the parp inhibitor 2-(4-trifluoro-methylphenyl)benzimidazole-4-carboxamide (NU1077)
  作者：Steven C. Austen、John M. Kane

  DOI：10.1002/jhet.5570380427

  日期：2001.7

  A four-step synthesis of the PARP inhibitor 2-(4-trifluoromethylphenyl)benzimidazole-4-carboxamide (1, NU1077) is presented. Condensation of 2,3-diaminotoluene and 4-trifluoromethylbenzaldehyde afforded 4-methyl-2-(4-trifluoromethylphenyl)benzimidazole. Oxidation of the methyl group with potassium permanganate in warm t-butanol afforded the carboxylic acid that was converted to the corresponding carboxamide

  提出了一种四步合成PARP抑制剂2-（4-三氟甲基苯基）苯并咪唑-4-羧酰胺（1，NU1077）。2，3-二氨基甲苯和4-三氟甲基苯甲醛的缩合得到4-甲基-2-（4-三氟甲基苯基）苯并咪唑。在温暖的叔丁醇中用高锰酸钾氧化甲基，得到羧酸，其通过酰氯转化为相应的羧酰胺。
• Synthesis and antifungal activity of substituted salicylaldehyde hydrazones, hydrazides and sulfohydrazides
  作者：Gregory L. Backes、Donna M. Neumann、Branko S. Jursic

  DOI：10.1016/j.bmc.2014.07.022

  日期：2014.9

  Efficient synthetic procedures for the preparation of acid hydrazines and hydrazides were developed by converting the corresponding carboxylic acid into the methyl ester catalyzed by Amberlyst-15, followed by a reaction with hydrazine monohydrate. Sulfohydrazides were prepared from the corresponding sulfonyl chlorides and hydrazine monohydrate. Both of these group of compounds were condensed with substituted

  通过将相应的羧酸转化成由Amberlyst-15催化的甲酯，然后与一水合肼反应，开发出了用于制备酰肼和酰肼的有效合成方法。磺酰肼由相应的磺酰氯和肼一水合物制备。使用梯度浓缩方法将这两组化合物与取代的水杨醛缩合，生成大量的,、酰肼和磺酰肼类似物库。制备的类似物的抗真菌活性表明，水杨醛hydr和酰肼是有效的真菌生长抑制剂，几乎没有哺乳动物细胞毒性，这使这些类似物成为未来治疗发展的新靶标。
• 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
• Enhancers of Protein Degradation
  申请人：Wanker Erich

  公开号：US20120282629A1

  公开（公告）日：2012-11-08

  The present invention relates to compounds suitable for modulating huntingtin protein processing and useful for treating or preventing huntingtin-related disorders. The invention provides pharmaceutical compositions comprising said compounds and methods of syntheses thereof.

  本发明涉及适用于调节亨廷顿蛋白处理并用于治疗或预防亨廷顿相关疾病的化合物。本发明提供了包含所述化合物的药物组合物以及其合成方法。
• Mayadeo, M. S.; Sinha, C. H.; Kale, S. S., Journal of the Indian Chemical Society, 1986, vol. 63, p. 694 - 696
  作者：Mayadeo, M. S.、Sinha, C. H.、Kale, S. S.

  DOI：——

  日期：——