N'-(4-chlorobenzylidene)isonicotinohydrazide

• 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: N'-(4-chlorobenzylidene)isonicotinohydrazide
• 英文别名: N-[(4-chlorophenyl)methylideneamino]pyridine-4-carboxamide；isonicotinic acid N2-(4-chlorobenzylidene)hydrazide；N-isonicotinamido-4-chlorobenzalaldimine；N1-(4-chlorobenzylidene) isonicotinohydrazide
• 化学式: C₁₃H₁₀ClN₃O
• mdl: MFCD00030953
• 分子量: 259.695
• InChiKey: AMDRLZATAWMLKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  3

反应信息

• 作为反应物：
  描述：

  N'-(4-chlorobenzylidene)isonicotinohydrazide 在 ammonium cerium(IV) nitrate 作用下， 反应 0.33h， 以78%的产率得到2-(4-chlorophenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  一锅合成不对称2,5-二取代1,3,4-恶二唑的简便方法

  摘要：

  不对称的2，5-二取代的1,3,4-恶二唑是通过酰基的环化-氧化反应有效合成的。同样，标题化合物的合成是通过在硝酸铈铵中在二氯甲烷中缩合酰肼和芳族醛来实现的。

  DOI：

  10.1016/j.tetlet.2006.07.127
• 作为产物：
  描述：

  异烟酸 在 硫酸 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 N'-(4-chlorobenzylidene)isonicotinohydrazide
  参考文献：
  名称：

  Synthesis and testing of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazole derivatives for antifungal activity against selected Candida Species

  摘要：

  A series of 21 1,3,4-oxadiazoline derivatives was synthesized by cyclization of N-acylhydrazones with acetic anhydride and evaluated for their in vitro antifungal activity against six Candida strains: Candida albicans (ATCC 90028 and LM V-42), C. krusei (ATCC 6258 and LM 12 C) and C. tropicalis (ATCC 13803 and LM 14). The Candida strains were found to be sensitive to some of the compounds, which inhibited the growth by 50-90%, with minimum inhibitory concentration (MIC) in the range of 64-512 mu g mL(-1). The compounds' structures were fully confirmed and characterized by Fourier transform infrared spectroscopy (FTIR), H-1 and C-13 nuclear magnetic resonance (NMR) and mass spectrometry (MS).

  DOI：

  10.1590/s0103-50532013000100016

文献信息

• One-Pot, Three Component Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles Catalyzed by Heteropolyacid
  作者：Majid M. Heravi、Vahideh Zadsirjan、Khadijeh Bakhtiari、Fatemeh F. Bamoharram

  DOI：10.1080/15533174.2012.740718

  日期：2013.3.1

  H6[PMo9V3O40] was used as an efficient catalyst for the preparation of 1-aroyl-2-arylidene hydrazines. 2,5-Disubstituted 1,3,4-oxadiazoles have been synthesized by oxidation of 1-aroyl-2-arylidene hydrazines with CrO3 in excellent yields.

  H 6 [PMo 9 V 3 O 40 ]被用作制备1-芳酰基-2-亚芳基肼的有效催化剂。已经通过用CrO 3氧化1-芳基-2-亚芳基肼以优异的产率合成了2，5-二取代的1,3,4-恶二唑。
• Microwave-Assisted, Solvent-Free and Parallel Synthesis of Some Novel Substituted Imidazoles of Biological Interest
  作者：Gyanendra Kumar Sharma、Devender Pathak

  DOI：10.1248/cpb.58.375

  日期：——

  of some novel substituted imidazoles of biological interest is reported. First, primary aromatic or heteryl amine was condensed with aryl or heteryl aldehydes to afford corresponding Schiff's base. The Schiff's base further on treatment with ammonium acetate (NH(4)OAC) and isatin using silica gel as the solid support, yielded the corresponding aryl imidazoles. In this paper a comparative study between

  据报道，无溶剂微波辅助合成了一些具有生物学意义的新型取代的咪唑。首先，将伯芳族或杂胺与芳基或杂醛缩合，得到相应的席夫碱。席夫氏碱进一步用醋酸铵（NH（4）OAC）和靛红使用硅胶作为固体载体处理，得到相应的芳基咪唑。本文介绍了已开发的微波方法与常规方法之间的对比研究。通过物理和分析数据分析了合成的化合物。评价了合成的化合物的抗菌，驱虫，短期抗癌和抗结核活性。所有合成的取代的咪唑均显示出对革兰氏阴性细菌肺炎克雷伯菌和大肠杆菌具有良好的抗菌活性，并具有中等至良好的驱虫活性。合成的咪唑衍生物对Ehrlich腹水癌（EAC）细胞系具有明显的细胞毒活性。这些化合物均未显示出显着的抗结核活性。
• 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。
• 3-Acetyl-2,5-diaryl-2,3-dihydro-1,3,4-oxadiazoles: A New Scaffold for the Selective Inhibition of Monoamine Oxidase B
  作者：Elias Maccioni、Stefano Alcaro、Roberto Cirilli、Sara Vigo、Maria Cristina Cardia、Maria Luisa Sanna、Rita Meleddu、Matilde Yanez、Giosuè Costa、Laura Casu、Peter Matyus、Simona Distinto

  DOI：10.1021/jm2002876

  日期：2011.9.22

  3-Acetyl-2,5-diaryl-2,3-dihydro-1,3,4-oxadiazoles were designed, synthesized, and tested as inhibitors against human monoamine oxidase (MAO) A and B isoforms. Several compounds, obtained as racemates, were identified as selective MAO-B inhibitors. The enantiomers of some derivatives were separated by enantioselective HPLC and tested. The R-enantiomers always showed the highest activity. Docking study

  设计，合成并测试了3-乙酰基-2,5-二芳基-2,3-二氢-1,3,4-恶二唑类化合物作为抗人单胺氧化酶（MAO）A和B同工型的抑制剂。鉴定为外消旋体的几种化合物被鉴定为选择性MAO-B抑制剂。通过对映选择性HPLC分离并测试了一些衍生物的对映异构体。在[R对映体总活性最高。对接研究和分子动力学模拟证明了推定的结合模式。我们得出的结论是，这些1,3,4-恶二唑衍生物是有前途的可逆和选择性MAO-B抑制剂。