4-(hydrazonomethyl)benzene-1,3-diol | 52693-85-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(hydrazonomethyl)benzene-1,3-diol
• 英文别名: Benzaldehyde, 2,4-dihydroxy-, hydrazone；4-methanehydrazonoylbenzene-1,3-diol
• CAS: 52693-85-3
• 化学式: C₇H₈N₂O₂
• 分子量: 152.153
• InChiKey: CPXBROCRNFUYQD-UHFFFAOYSA-N

物化性质

• 沸点：
  384.9±35.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(hydrazonomethyl)benzene-1,3-diol 在 三乙胺 作用下， 以 苯 为溶剂， 反应 18.0h， 生成 2-(2,4-Dihydroxy-phenyl)-4-(5,6-diphenyl-[1,2,4]triazin-3-yl)-[1,3,4]thiadiazinan-5-one
  参考文献：
  名称：

  Abdel-Rahman, R. M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 815 - 819

  摘要：

  DOI：
• 作为产物：
  描述：

  (2,4-dihydroxy-benzylidene)-dimethyl-ammonium; dichloro phosphate 在 肼 作用下， 以 乙醇 、 水 为溶剂， 反应 5.5h， 生成 4-(hydrazonomethyl)benzene-1,3-diol
  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

• 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。
• Structure-based design, synthesis, and biological evaluation of novel piperine–resveratrol hybrids as antiproliferative agents targeting SIRT-2
  作者：Ahmed H. Tantawy、Xiang-Gao Meng、Adel A. Marzouk、Ali Fouad、Ahmed H. Abdelazeem、Bahaa G. M. Youssif、Hong Jiang、Man-Qun Wang

  DOI：10.1039/d1ra04061h

  日期：——

  A series of novel piperine-resveratrol hybrids 5a-h was designed, synthesized, and structurally elucidated by IR, and 1H, 13C, and 19F NMR. Antiproliferative activities of 5a-h were evaluated by NCI against sixty cancer cell lines. Compound 5b, possessing resveratrol pharmacophoric phenolic moieties, showed a complete cell death against leukemia HL-60 (TB) and Breast cancer MDA-MB-468 with growth inhibition

  设计、合成了一系列新型胡椒碱-白藜芦醇杂化物 5a-h，并通过 IR、1H、13C 和 19F NMR 对其结构进行了阐明。NCI 评估了 5a-h 对 60 种癌细胞系的抗增殖活性。具有白藜芦醇药效酚部分的化合物 5b 对白血病 HL-60 (TB) 和乳腺癌 MDA-MB-468 显示完全细胞死亡，生长抑制百分比分别为 -0.49 和 -2.83。此外，5b 记录了对其他癌细胞系的显着活性，其生长抑制百分比在 80 到 95 之间。评估了新的 5a-h 杂种对 Sirt-1 和 Sirt-2 作为其抗增殖作用的分子靶点的抑制活性。结果表明，化合物 5a-h 在 5 μm 和 50 μm 时对 Sirt-2 的抑制作用比 Sirt-1 更强。化合物 5b 对 Sirt-2 的抑制作用最强（分别在 50 μM 和 5 μM 时抑制 78 ± 3% 和 26 ± 3%）。通过 Hirschfeld