N′-(2-hydroxy-5-methoxybenzylidene)isonicotinohydrazide | 325472-20-6

• 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-methoxybenzylidene)isonicotinohydrazide
• 英文别名: N'-(2-hydroxy-5-methoxybenzylidene)isonicotinohydrazide；N-[(2-hydroxy-5-methoxyphenyl)methylideneamino]pyridine-4-carboxamide
• CAS: 325472-20-6
• 化学式: C₁₄H₁₃N₃O₃
• mdl: MFCD00643720
• 分子量: 271.276
• InChiKey: UFEIPZRPZZVFSH-UHFFFAOYSA-N

物化性质

• 密度：
  1.25±0.1 g/cm3(Predicted)

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：

  N′-(2-hydroxy-5-methoxybenzylidene)isonicotinohydrazide 、 copper dichloride 以 甲醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  设计水杨醛异烟酰酰azo作为具有可调螯合和释放铜的铜（II）离子载体，以击中癌细胞的氧化跟腱

  摘要：

  与正常细胞相比，在癌细胞中观察到更高水平的铜，还原型谷胱甘肽（GSH）和活性氧（ROS），赞成将铜离子载体开发为促氧化抗癌剂（PAA）来达到改变的氧化还原稳态的想法（氧化还原阿基里斯脚跟） ）的癌细胞。在这项工作中，我们使用水杨醛异烟酰yl（SIH-1）作为碱性支架，通过在对位引入吸电子硝基和给电子甲氧基来设计具有可调节的螯合和释放Cu（II）的Cu（II）离子载体。酚羟基位置，或通过使用甲基封闭酚羟基位点。这些分子被用来探测铜的螯合和释放如何影响它们的离子作用和靶向癌细胞氧化还原阿基里斯足跟的能力。在这些分子中，SIH-1被认为是比HUVEC细胞更能优先杀死HepG2细胞的最有力的Cu（II）离子载体，并且在相对较高的细胞毒性和更好的选择性方面，它还优于临床试验中评估的铜离子载体氯碘喹。尽管SIH-1形成的Cu（II）配合物比其他分子具有更高的稳定常数，但其较高的氧化电位是由GSH释放铜

  DOI：

  10.1016/j.freeradbiomed.2018.09.017
• 作为产物：
  描述：

  异烟酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 N′-(2-hydroxy-5-methoxybenzylidene)isonicotinohydrazide
  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。
• Syntheses, crystal structures, and catalysis by polymeric dioxomolybdenum(VI) complexes with similar (iso)nicotinohydrazones
  作者：Wei-Xiu Xu、Yong-Mei Yuan、Wen-Hui Li

  DOI：10.1080/00958972.2013.816416

  日期：2013.8.1

  Polymeric dioxomolybdenum(VI) complexes, [MoO2L](n) (L=L-1=N-(2-hydroxybenzylidene)nicotinohydrazide for 1, L=L-2=N-(2-hydroxy-5-methoxybenzylidene)isonicotinohydrazide for 2), were prepared and characterized by physico-chemical, spectroscopic methods, and single-crystal X-ray determination. Complex 1 crystallizes in the orthorhombic space group P2(1)2(1)2(1) with a=7.6568(4), b=11.6315(7), c=15.2211(9)angstrom, V=1355.59(13)angstrom(3), Z=4, R-1=0.0181, wR(2)=0.0464, and S=1.097. Complex 2 crystallizes in the monoclinic space group P2(1)/n with a=11.2516(6), b=11.8134(7), c=12.4371(6)angstrom, =116.2210(10)degrees, V=1483.02(14)angstrom(3), Z=4, R-1=0.0399, wR(2)=0.0874, and S=1.096. X-ray analysis indicates that Mo in each complex is octahedral with two oxo groups and N2O2 donor set of the nicotinohydrazone or isonicotinohydrazone. The complexes are efficient catalysts for oxidation of olefins.
• 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.
• Designing salicylaldehyde isonicotinoyl hydrazones as Cu(II) ionophores with tunable chelation and release of copper for hitting redox Achilles heel of cancer cells
  作者：Yuan Ji、Fang Dai、Bo Zhou

  DOI：10.1016/j.freeradbiomed.2018.09.017

  日期：2018.12

  molecules, SIH-1 was identified as the most potent Cu(II) ionophore to kill preferentially HepG2 cells over HUVEC cells, and also superior to clioquinol, a copper ionophore evaluated in clinical trials, in terms of its relatively higher cytotoxicity and better selectivity. Higher oxidative potential, despite of lower stability constant, of the Cu(II) complex formed by SIH-1 than by the other molecules, is

  与正常细胞相比，在癌细胞中观察到更高水平的铜，还原型谷胱甘肽（GSH）和活性氧（ROS），赞成将铜离子载体开发为促氧化抗癌剂（PAA）来达到改变的氧化还原稳态的想法（氧化还原阿基里斯脚跟） ）的癌细胞。在这项工作中，我们使用水杨醛异烟酰yl（SIH-1）作为碱性支架，通过在对位引入吸电子硝基和给电子甲氧基来设计具有可调节的螯合和释放Cu（II）的Cu（II）离子载体。酚羟基位置，或通过使用甲基封闭酚羟基位点。这些分子被用来探测铜的螯合和释放如何影响它们的离子作用和靶向癌细胞氧化还原阿基里斯足跟的能力。在这些分子中，SIH-1被认为是比HUVEC细胞更能优先杀死HepG2细胞的最有力的Cu（II）离子载体，并且在相对较高的细胞毒性和更好的选择性方面，它还优于临床试验中评估的铜离子载体氯碘喹。尽管SIH-1形成的Cu（II）配合物比其他分子具有更高的稳定常数，但其较高的氧化电位是由GSH释放铜