isovanillin isonicotinoylhydrazone | 106473-56-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: isovanillin isonicotinoylhydrazone
• 英文别名: N’-(3-hydroxy-4-methoxybenzylidene)isonicotinohydrazide；N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]pyridine-4-carboxamide
• CAS: 106473-56-7
• 化学式: C₁₄H₁₃N₃O₃
• mdl: MFCD00427614
• 分子量: 271.276
• InChiKey: YWQQOMZWDINTLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：

  cobalt(II) diacetate tetrahydrate 、 isovanillin isonicotinoylhydrazone 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Puri, Vanita; Agarwala, Badri V., Journal of the Indian Chemical Society, 1998, vol. 75, # 1, p. 27 - 28

  摘要：

  DOI：
• 作为产物：
  描述：

  异香兰素 、 异烟肼 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以70%的产率得到isovanillin isonicotinoylhydrazone
  参考文献：
  名称：

  有前景的Ag（I）与N-酰基hydr与芳香醛和异烟肼的复合物，在结核病中具有多重耐药性

  摘要：

  在本工作中，描述了N-酰基hydr衍生物及其相应的银（I）配合物的合成，表征和抗结核试验。通过元素分析，IR和NMR光谱测量，摩尔电导率测定和粉末衍射X射线研究对化合物进行表征。一些合成的化合物对结核分枝杆菌H37Rv（ATCC 27294）的最低抑制浓度（MIC 90）值低于0.098 µg / mL，而对MRC-5细胞的细胞毒活性测定表明，所有化合物的选择性指数均高于27.此外，N-酰基hydr唑酮化合物即使对耐多药耐药的临床菌株也显示出令人鼓舞的活性。结核分枝杆菌。

  DOI：

  10.1016/j.molstruc.2021.130193

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。
• 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.
• Acylhydrazones as isoniazid derivatives with multi-target profiles for the treatment of Alzheimer’s disease: Radical scavenging, myeloperoxidase/acetylcholinesterase inhibition and biometal chelation
  作者：Daniela Corrêa Santos、Ruan Roberto Henriques、Marcos Antonio de Abreu Lopes Junior、André Borges Farias、Thayssa Lisboa do Couto Nogueira、João Victor Fernandes Quimas、Nelilma Correia Romeiro、Leandro Louback da Silva、Andréa Luzia Ferreira de Souza

  DOI：10.1016/j.bmc.2020.115470

  日期：2020.5

  Acylhydrazones la-o, derived from isoniazid, were synthesized and evaluated for Myeloperoxidase (MPO) and Acetylcholinesterase (AChE) inhibition, as well as their antioxidant and metal chelating activities, with the purpose of investigating potential multi-target profiles for the treatment of Alzheimer's disease. Synthesized compounds were tested using the 2,2-diphenyl-2-picrylhydrazyl (DPPH) method and 1i, 1j and 1 m showed radical scavenging ability. Compounds 1b, 1 h, 1i , 1 m and 1o inhibited MPO activity (10 mu M) at 96.1 +/- 5.5%, 90 +/- 2.1%, 100.3 +/- 1.7%, 80.1 +/- 9.4% and 82.2 +/- 10.6%, respectively, and only compound 1 m was able to inhibit 54.2 +/- 1.7% of AChE activity (100 mu M). Docking studies of the most potent compound 1 m were carried out, and the computational results provided the theoretical basis of enzyme inhibition. Furthermore, compound 1 m was able to form complexes with Fe2+ and Zn2+ ions in a 2:1 ligand:metal ratio according to the Job Plot method.
• Promising Ag(I) complexes with N-acylhydrazones from aromatic aldehydes and isoniazid against multidrug resistance in tuberculosis
  作者：Paulo Victor P. dos Santos、Camila M. Ribeiro、Fernando R. Pavan、Pedro P. Corbi、Fernando R.G. Bergamini、Marcos A. Carvalho、Kaique A. D'Oliveria、Alexandre Cuin

  DOI：10.1016/j.molstruc.2021.130193

  日期：2021.6

  In the present work, synthesis, characterization and antitubercular assays of N-acylhydrazones derivatives and their corresponding silver(I) complexes are described. The compounds were characterized by elemental analysis, IR and NMR spectroscopic measurements, molar conductivity assays and powder diffraction X ray studies. Some of the synthesized compounds have shown minimum inhibitory concentration

  在本工作中，描述了N-酰基hydr衍生物及其相应的银（I）配合物的合成，表征和抗结核试验。通过元素分析，IR和NMR光谱测量，摩尔电导率测定和粉末衍射X射线研究对化合物进行表征。一些合成的化合物对结核分枝杆菌H37Rv（ATCC 27294）的最低抑制浓度（MIC 90）值低于0.098 µg / mL，而对MRC-5细胞的细胞毒活性测定表明，所有化合物的选择性指数均高于27.此外，N-酰基hydr唑酮化合物即使对耐多药耐药的临床菌株也显示出令人鼓舞的活性。结核分枝杆菌。
• Puri, Vanita; Agarwala, Badri V., Journal of the Indian Chemical Society, 1998, vol. 75, # 1, p. 27 - 28
  作者：Puri, Vanita、Agarwala, Badri V.

  DOI：——

  日期：——