2-Fluoro-benzaldehyde isonicotinoylhydrazone | 144293-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-Fluoro-benzaldehyde isonicotinoylhydrazone
• 英文别名: N1-(2-fluorobenzylidene) isonicotinohydrazide；N-[(2-fluorophenyl)methylideneamino]pyridine-4-carboxamide；(4E)-N-[(2-fluorophenyl)methylidene]pyridine-4-carbohydrazonic acid
• CAS: 144293-93-6
• 化学式: C₁₃H₁₀FN₃O
• 分子量: 243.24
• InChiKey: ZOENMAIIAUYBFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  54.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Fluoro-benzaldehyde isonicotinoylhydrazone 在 potassium permanganate 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 生成 N-[2-(2-Fluoro-phenyl)-1,1,4-trioxo-1λ⁶-thiazolidin-3-yl]-isonicotinamide
  参考文献：
  名称：

  Vigorita; Basile; Zappala, Il Farmaco, 1992, vol. 47, # 6, p. 893 - 906

  摘要：

  DOI：
• 作为产物：
  描述：

  异烟肼 、 2-氟苯甲醛 以 乙醇 为溶剂， 以89 %的产率得到2-Fluoro-benzaldehyde isonicotinoylhydrazone
  参考文献：
  名称：

  Synthesis, spectral characterization, and biological activities of novel palladium(II) and platinum(II) complexes of active Schiff base ligands

  摘要：

  摘要。配体 N-(2-氟亚苄基)异烟酰腙（L1H）和 N-(2-氟苯乙酮)异烟酰腙（L2H）与钯盐酸盐（PdCl2）和铂盐酸盐（PtCl2）相互作用，合成了一系列新的钯(II)和铂(II)希夫碱配合物。研究人员利用元素分析、熔点测定、分子量测定、红外光谱、1H NMR 和紫外-可见光谱研究来描述配体及其金属配合物的结构和成键模式。这些分析表明，配体与金属离子的配位方式为单基双齿配位，配合物的几何形状为正方形。这两种配体及其钯（II）和铂（II）配合物的抗菌活性已针对多种细菌和真菌菌株进行了测试，并显示出相当的抗真菌和抗细菌特性。铂（L2H）]Cl2 复合物的体外细胞毒性活性是通过 MTT 法检测其抑制人 HeLa 细胞系（宫颈癌细胞系）细胞增殖的潜力来评估的，而 [Pt(L1H)2]Cl2 复合物的抗氧化活性则是通过 DPPH 法来检测的。结果表明，铂（II）复合物具有剂量依赖性的细胞毒性和自由基清除活性，因此具有重要的生物学意义； 关键字：希夫碱配体、抗菌活性、清除活性、细胞毒性 ； Bull.Chem.Soc.2023, 37(6), 1383-1396.DOI: https://dx.doi.org/10.4314/bcse.v37i6.7

  DOI：

  10.4314/bcse.v37i6.7

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。
• Nicotinic acid hydrazones: a novel anticonvulsant pharmacophore
  作者：Reema Sinha、U. V. Singh Sara、R. L. Khosa、James Stables、Jainendra Jain

  DOI：10.1007/s00044-010-9396-0

  日期：2011.12

  amino transferase (GABA-AT) in Lamarckian genetic algorithm based flexible docking studies. Compound D 8, N 1-(4-chlorobenzylidene) nicotinohydrazide was found to be the most potent analog with ED50 value of 16.1 mg/kg and protective index (PI = TD50/ED50) value of >20, which was much greater than that of the prototype drug phenytoin (PI = 6.9). It has shown free binding energy value of −10.20 kcal/mol

  合成了一系列取代的芳族酰肼（D 1至D 20）的芳酸azo，并评价了其抗惊厥活性。烟酸酰肼（D 8，D 9和D 10）的芳酰azo在最大的电击筛选中显示了出色的保护作用。在基于Lamarckian遗传算法的灵活对接研究中，这些化合物还显示了与γ氨基丁酸氨基转移酶（GABA-AT）的Lys 329残基的优异结合特性。化合物D 8，N 1发现（-4-氯苄叉）烟酰肼是最有效的类似物，ED 50值为16.1 mg / kg，保护指数（PI = TD 50 / ED 50）值> 20，远大于原型样品。药物苯妥英钠（PI = 6.9）。它显示出对GABA-AT的自由结合能值为-10.20 kcal / mol，抑制常数（Ki）值为33.30 nM，这表明烟酸酰肼的芳酸azo可作为新型抗惊厥药的设计中的新药效团。毒品。
• Mechanistic differences between in vitro assays for hydrazone-based small molecule inhibitors of anthrax lethal factor
  作者：M. Leslie Hanna、Theodore M. Tarasow、Julie Perkins

  DOI：10.1016/j.bioorg.2006.07.004

  日期：2007.2

  A systematically generated series of hydrazones were analyzed as potential inhibitors of anthrax lethal factor. The hydrazones were screened using one UV-based and two fluorescence-based in vitro assays. The study identified several inhibitors with IC50 values in the micromolar range, and importantly, significant differences in the types of inhibition were observed with the different assays. (c) 2006 Elsevier Inc. All rights reserved.
• Synthesis and biological screening of some pyridine derivatives as anti-malarial agents
  作者：Adnan A. Bekhit、Ariaya Hymete、Ashenafi Damtew、Abdel Maaboud I. Mohamed、Alaa El-Din A. Bekhit

  DOI：10.3109/14756366.2011.575071

  日期：2012.2.1

  Two series of pyridine derivatives were synthesised and evaluated for their in vivo anti-malarial activity against Plasmodium berghei. The anti-malarial activity was determined in vivo by applying 4-day standard suppressive test using chloroquine (CQ)-sensitive P. berghei ANKA strain-infected mice. Compounds 2a, 2g and 2h showed inhibition of the parasite multiplication by 90, 91 and 80%, respectively, at a dose level of 50 mu mol/kg. Moreover, The most active compounds (2a, 2g and 2h) were tested in vitro against CQ-resistant Plasmodium falciparum RKL9 strains where compound 2g showed promising activity with IC50 = 0.0402 mu M. The compounds were non-toxic at 300 and 100 mg/kg through the oral and parenteral routes, respectively. The docking pose of the most active compounds (2a, 2g and 2h) in the active site of dihydrofolate reductase enzyme revealed several hydrogen and hydrophobic interactions that contribute to the observed anti-malarial activities.
• Vigorita; Ottana; Zappala, Revista Bras il eira de Farmaco gnosia, 1995, vol. 50, # 11, p. 783 - 786
  作者：Vigorita、Ottana、Zappala、Maccari、Pizzimenti、Gabbrielli

  DOI：——

  日期：——