(E)-N'-(2-hydroxybenzylidene)picolinohydrazide | 15075-87-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-N'-(2-hydroxybenzylidene)picolinohydrazide
• 英文别名: N'-[(E)-(2-hydroxyphenyl)methylidene]pyridine-2-carbohydrazide；N-[(E)-(2-hydroxyphenyl)methylideneamino]pyridine-2-carboxamide
• CAS: 15075-87-3
• 化学式: C₁₃H₁₁N₃O₂
• 分子量: 241.249
• InChiKey: JROVPEHJQHDYQV-OQLLNIDSSA-N

物化性质

• 熔点：
  174-175 °C
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 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：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-吡啶甲酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 (E)-N'-(2-hydroxybenzylidene)picolinohydrazide
  参考文献：
  名称：

  Potent antimicrobial agents against azole-resistant fungi based on pyridinohydrazide and hydrazomethylpyridine structural motifs

  摘要：

  Schiff base derivatives have recently been shown to possess antimicrobial activity, and these derivatives include a limited number of salicylaldehyde hydrazones. To further explore this structure-activity relationship between salicylaldehyde hydrazones and antifungal activity, we previously synthesized and analyzed a large series of salicylaldehyde and formylpyridinetrione hydrazones for their ability to inhibit fungal growth of both azole-susceptible and azole-resistant species of Candida. While many of these analogs showed excellent growth inhibition with low mammalian cell toxicity, their activity did not extend to azole-resistant species of Candida. To further dissect the structural features necessary to inhibit azole-resistant fungal species, we synthesized a new class of modified salicylaldehyde derivatives and subsequently identified a series of modified pyridine-based hydrazones that had potent fungicidal antifungal activity against multiple Candida spp. Here we would like to present our synthetic procedures as well as the results from fungal growth inhibition assays, mammalian cell toxicity assays, time-kill assays and synergy studies of these novel pyridine-based hydrazones on both azole-susceptible and azole-resistant fungal species. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.040

文献信息

• Facile synthesis of 1-substituted 4-H phthalazine, a versatile scaffold for chemically diverse phthalazines
  作者：Rungsima Hadsarung、Sanit Thongnest、Sittisak Oekchuae、Duangduan Chaiyaveij、Jutatip Boonsombat、Somsak Ruchirawat

  DOI：10.1016/j.tet.2022.132920

  日期：2022.8

  An improved synthetic strategy for 1-substituted 4-H phthalazines using a convenient, three-step reaction sequence under mild conditions is described. The protocol involves condensation of hydrazine hydrate with o-ketobenzaldehydes derived through the Pb(OAc)4 oxidation of the N-acylhydrazones of salicylaldehydes. This pathway is of high practical value since a wide variety of substituted acylhydrazides

  描述了在温和条件下使用方便的三步反应序列改进 1-取代 4-H 酞嗪的合成策略。该协议涉及水合肼与通过水杨醛的N-酰基腙的 Pb(OAc) 4氧化衍生的邻酮苯甲醛的缩合。该途径具有很高的实用价值，因为种类繁多的取代酰肼和水杨醛是N-酰基腙是可商购的。此外，三步序列可以扩大规模，无需中间纯化，以高产率提供广泛的产品。1-苯基 4-H 酞嗪是一种多功能化合物，可提供多种酞嗪类似物，包括血管扩张剂 MY5445。
• N-acylhydrazones confer inhibitory efficacy against New Delhi metallo-β-lactamase-1
  作者：Han Gao、Jia-Qi Li、Peng-Wei Kang、Jia-Zhu Chigan、Huan Wang、Lu Liu、Yin-Sui Xu、Le Zhai、Ke-Wu Yang

  DOI：10.1016/j.bioorg.2021.105138

  日期：2021.9
• Acylhydrazones of o-Oxy- and o-Aminoaldehydes and Ketones as Tridentate Complexing Agents
  作者：Luigi Sacconi

  DOI：10.1021/ja01117a519

  日期：1953.11
• Grammaticakis, Bulletin de la Societe Chimique de France, 1955, p. 1471,1473
  作者：Grammaticakis

  DOI：——

  日期：——
• Dutta, R. L.; Das, B. R., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1983, vol. 22, # 3, p. 207 - 210
  作者：Dutta, R. L.、Das, B. R.

  DOI：——

  日期：——