N’-(2-hydroxy-5-methoxyphenylmethylidene)-3-pyridinecarbohydrazide

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N’-(2-hydroxy-5-methoxyphenylmethylidene)-3-pyridinecarbohydrazide
• 英文别名: N'-(2-hydroxy-5-methoxyphenylmethylidene)-3-pyridinecarbohydrazide；N-[(2-hydroxy-5-methoxyphenyl)methylideneamino]pyridine-3-carboxamide
• 化学式: C₁₄H₁₃N₃O₃
• mdl: MFCD00185234
• 分子量: 271.276
• InChiKey: ZMEAVUOVFKUQMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  硫酸氧钒水合物 、 N’-(2-hydroxy-5-methoxyphenylmethylidene)-3-pyridinecarbohydrazide 以 乙醇 为溶剂， 反应 0.67h， 以73%的产率得到
  参考文献：
  名称：

  水杨腙席夫碱钒(IV)和(V)配合物的表征和抗糖尿病活性

  摘要：

  分离出基于 5-硝基水杨醛、5-甲氧基水杨醛或 5-磺基水杨醛和各自酰肼的三齿席夫碱配体的 24 种氧化钒 (IV, V) 配合物，并使用物理化学和光谱方法对其进行表征。其中三个通过单晶 X 射线结构测定进行结构表征。生物活性研究包括对人酪氨酸磷酸酶的抑制、对肌细胞 C2C12、脂肪细胞 3T3-L1 和人肝细胞 HepG2 细胞系的研究、肌细胞和脂肪细胞的葡萄糖摄取以及细胞毒性试验。在溶液中不稳定的复合物表现出其他 V(IV) 复合物的典型生物活性，而稳定的复合物则表现出更高的配体依赖性活性。

  DOI：

  10.1007/s11243-020-00437-1
• 作为产物：
  描述：

  烟酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 N’-(2-hydroxy-5-methoxyphenylmethylidene)-3-pyridinecarbohydrazide
  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

• Antimicrobial Activities of Synthetic Arylidine Nicotinic and Isonicotinic Hydrazones
  作者：Muhammad Hayat、Khalid Mohammed Khan、Sumayya Saeed、Uzma Salar、Momin Khan、Taimoor Baig、Aqeel Ahmad、Shahnaz Parveen、Muhammad Taha

  DOI：10.2174/1570180814666170914120337

  日期：2018.8.27

  showed significant to moderate antimicrobial activities against Gram positive and Gram negative bacterial cultures. Few compounds also showed antifungal activity against fungal cultures. Minimum Inhibitory Concentration (MIC) was calculated for the most active compounds 1, 7, 11, 19, 34, 46, 50, 51, and 55 against gram positive and gram negative cultures. Conclusion: Newly identified compounds may serve

  背景：尽管可以使用多种抗菌剂，但病原菌的再次出现仍然是严重的医学问题。鉴定新的，安全的和选择性的抗菌剂是药物化学研究的主要兴趣。 方法：研究了合成的亚芳基烟碱和异烟碱（1-63）库的抗菌活性。 结果：许多衍生物显示出对革兰氏阳性和革兰氏阴性细菌培养物具有显着至中等的抗菌活性。很少有化合物也显示出对真菌培养物的抗真菌活性。计算了对革兰氏阳性和革兰氏阴性培养物活性最高的化合物1、7、11、19、34、46、50、51和55的最低抑菌浓度（MIC）。 结论：新鉴定的化合物可作为未来研究的先导，以获得更强大的抗菌剂。
• Gallium(III) complexes of aroylhydrazones derived from nicotinic acid hydrazide in solid state and in solution
  作者：Marijana Pocrnić、Darko Kontrec、Snežana Miljanić、Željka Soldin、Ana Budimir、Nives Galić

  DOI：10.1016/j.molstruc.2020.129564

  日期：2021.3

  β2) with ligands H2L1−H2L4 amounted to 12.4, 11.5, 10.6 and 11.2 respectively, showing that additional methoxy group in meta position decreases stability of complexes. The complexes isolated from ethanolic solution had 1:2 (metal:ligand) stoichiometry. In all complexes the remaining charge of metal ion was neutralized by nitrate ions as shown by IR spectroscopy. Only for H2L2 the keto-enol tautomeric

  摘要 N'-salicylidene-3-pyridinecarbohydrazide (H2L1), N'-(2-羟基-3-甲氧基苯基亚甲基)-3-吡啶碳酰肼 (H2L2), N'-(2-羟基-4-甲氧基苯基亚甲基)-的配位性质3-吡啶碳酰肼 (H2L3) 和 N'-(2-羟基-5-甲氧基苯基亚甲基)-3-吡啶碳酰肼 (H2L4) 对 Ga(III) 离子作为 Fe(III) 离子的模拟物在固态和溶液中进行了研究质谱、紫外-可见和红外光谱技术。在不同的 pH 值和甲醇/水混合物下探测结合特性。在 pH 2.52 的甲醇/水 1/1 系统中，形成了与 Ga(III) 的 1:1 和 1:2 配合物，并通过紫外-可见光谱测定了相应的稳定性常数。Ga(III) 配合物 (log β2) 与配体 H2L1-H2L4 的累积常数分别为 12.4、11.5、10.6 和 11。图 2 分别表明间位的
• Potent antimicrobial agents against azole-resistant fungi based on pyridinohydrazide and hydrazomethylpyridine structural motifs
  作者：Gregory L. Backes、Branko S. Jursic、Donna M. Neumann

  DOI：10.1016/j.bmc.2015.04.040

  日期：2015.7

  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.
• Characterization and antidiabetic activity of salicylhydrazone Schiff base vanadium(IV) and (V) complexes
  作者：Janusz Szklarzewicz、Anna Jurowska、Maciej Hodorowicz、Grzegorz Kazek、Barbara Mordyl、Elżbieta Menaszek、Jacek Sapa

  DOI：10.1007/s11243-020-00437-1

  日期：2021.3

  Twenty-four oxidovanadium(IV,V) complexes with tridentate Schiff base ligands based on 5-nitrosalicylaldehyde, 5-methoxysalicylaldehyde, or 5-sulfosalicylaldehyde and respective hydrazide were isolated, and characterized using physicochemical and spectroscopic methods. Three of them were structurally characterized by single-crystal X-ray structure determination. The biological activity studies included

  分离出基于 5-硝基水杨醛、5-甲氧基水杨醛或 5-磺基水杨醛和各自酰肼的三齿席夫碱配体的 24 种氧化钒 (IV, V) 配合物，并使用物理化学和光谱方法对其进行表征。其中三个通过单晶 X 射线结构测定进行结构表征。生物活性研究包括对人酪氨酸磷酸酶的抑制、对肌细胞 C2C12、脂肪细胞 3T3-L1 和人肝细胞 HepG2 细胞系的研究、肌细胞和脂肪细胞的葡萄糖摄取以及细胞毒性试验。在溶液中不稳定的复合物表现出其他 V(IV) 复合物的典型生物活性，而稳定的复合物则表现出更高的配体依赖性活性。