N'-(4-hydroxybenzylidene)isonicotinohydrazide | 840-81-3

• 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-hydroxybenzylidene)isonicotinohydrazide
• 英文别名: N-[(4-hydroxyphenyl)methylideneamino]pyridine-4-carboxamide
• CAS: 840-81-3
• 化学式: C₁₃H₁₁N₃O₂
• mdl: MFCD00160917
• 分子量: 241.249
• InChiKey: MXEBNXXQDJLMTC-UHFFFAOYSA-N

物化性质

• 熔点：
  285-288 °C
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 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：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  N'-(4-hydroxybenzylidene)isonicotinohydrazide 在 碘 、 mercury(II) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 以60%的产率得到4-(5-Pyridin-4-yl-[1,3,4]oxadiazol-2-yl)-phenol
  参考文献：
  名称：

  Ishwar Bhat; Revanasiddappa; Prems, Jisha, Indian Journal of Heterocyclic Chemistry, 2011, vol. 21, # 2, p. 183 - 184

  摘要：

  DOI：
• 作为产物：
  描述：

  异烟肼 、 对羟基苯甲醛 在 三氟乙酸 作用下， 以 乙醇 为溶剂， 生成 N'-(4-hydroxybenzylidene)isonicotinohydrazide
  参考文献：
  名称：

  PhoP/PhoQ 抑制剂的效果导向合成以调节沙门氏菌毒力

  摘要：

  沙门氏菌属 是导致食源性感染的主要原因之一。PhoP/PhoQ 双组分调节系统是沙门氏菌的主要毒力调节剂。尽管 PhoP/PhoQ 是解除沙门氏菌毒力的理想目标，但迄今为止报道的抑制剂很少。我们描述了一种新的平台，通过该平台直接从含有氨基硫脲和单腙、二腙和三腙的反应介质中直接从大约 185 种化合物中选择一种抑制剂。为此，应用了串联文库制备、薄层色谱 (TLC) 生物自显影和效果导向反卷积。我们说明了这种以效果为导向的合成方法在识别食品领域新的有用生物活性化合物方面的潜力。

  DOI：

  10.1021/acs.jafc.2c01087

文献信息

• Design, Synthesis and Biological Evaluation of Some 2-Azetidinone Derivatives as Potential Antihyperlipidemic Agents
  作者：Nikhilesh Arya、Jaya Dwivedi、Vijay M. Khedkar、Evans C. Coutinho、Kishor S. Jain

  DOI：10.1002/ardp.201300262

  日期：2013.12

  develop new molecules with improved antihyperlipidemic activity, eight new 2‐azetidinone analogs (4a–4h) of ezetimibe were designed through in silico docking experiments with the crystal structure of the Niemann‐Pick C1‐like 1 protein (NPC1L1). Synthesis and further antihyperlipdemic evaluation of this series in the Triton WR 1339 induced hyperlipidemic rat model showed some of the molecules to exhibit significant

  为了开发具有改善的抗高血脂活性的新分子，通过与 Niemann-Pick C1 样 1 蛋白 (NPC1L1) 的晶体结构进行的计算机对接实验，设计了八种新的依折麦布 2-氮杂环丁酮类似物 (4a-4h)。在 Triton WR 1339 诱导的高脂血症大鼠模型中对该系列的合成和进一步抗高血脂评估表明，某些分子表现出与依折麦布相当的显着降脂作用。观察到观察到的生物活性与化合物的计算机分子对接评分之间的相关性。
• 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。
• Solvent-free mechanochemical route for green synthesis of pharmaceutically attractive phenol-hydrazones
  作者：P. F. M. Oliveira、M. Baron、A. Chamayou、C. André-Barrès、B. Guidetti、M. Baltas

  DOI：10.1039/c4ra10489g

  日期：——

  from various substituted organic hydrazines and phenol aldehydes. The degree of conversion was increased by high electronic density on the amino group of the hydrazine reactant, as well as low steric hindrance around both reactive sites. In this particular case, the flexibility of the chain bearing the amino reactive site of hydrazine was highlighted as a factor influencing the reaction rate. The results

  在振动球磨机中成功地由各种取代的有机肼和酚醛合成了一系列潜在的治疗剂azo。肼反应物氨基上的高电子密度以及两个反应位点附近的低位阻均提高了转化度。在这种特定情况下，带有肼的氨基反应位点的链的柔韧性被强调为影响反应速率的因素。结果表明，在不存在副产物的情况下，可以以超过99％的转化率获得。这高度适合于需要高纯度的活性药物成分的合成。
• Endothelium Dependent and Independent Mechanisms of Vasorelaxant Activity of Synthesized 2,5-disubstituted-1,3,4-oxadiazole Derivatives in Rat Thoracic Aorta - Ex vivo and Molecular Docking Studies
  作者：Zenab Attari、Jayesh Mudgal、Pawan G Nayak、Nandakumar Krishnadas、Revathi Rajappan、N. Gopalan Kutty

  DOI：10.2174/1570180812666150907203634

  日期：2016.4.14

  Background: Vasoconstriction is a major pathological feature of cardiovascular diseases involving endothelium dependent and independent mechanisms. Oxadiazole moiety appeared to be effective in various pathologies. Objective: The aim of the study was to synthesize and evaluate the mechanism of vasorelaxation exhibited by synthesized oxadiazole derivatives. Method: The 2,5-disubstituted-1,3,4-oxadiazole derivatives were synthesized by an efficient and simple method. The derivatives were investigated for their ex-vivo vasorelaxant action on intact/denuded endothelium rat aortic rings precontracted with norepinephrine/ phenylephrine/KCl. Results: The contractions induced in the aortic rings by the addition of cumulative concentrations of norepinephrine, phenylephrine, KCl and calcium were significantly antagonized by a derivative, OXD-Z2. In another experiment, verapamil pretreatment inhibited phenylephrine and Ca2+-induced aortic contractions and OXD-Z2 did not alter verapamilinduced inhibition. This indicated the role of L-type Ca2+-channels in the OXD-Z2-induced vasorelaxation via inhibition of calcium influx. Further, atropine (muscarinic receptor antagonist), L-NAME (NO synthase inhibitor) and methylene blue (non-selective cGMP inhibitor) inhibited OXD-Z2-induced relaxation in other sets of experiments. These results indicate that OXD-Z2 also mediates vasorelaxation through NO release by muscarinic receptor activation. In addition, the molecular docking studies showed that OXD-Z2 interacts with L-type Ca2+-channel, muscarinic (M2) receptor and eNOS. Conclusion: Thus, it is deduced from the above findings that the vasorelaxant activity of OXD-Z2 involves muscarinic receptor-mediated nitric oxide release in addition to direct inhibition of L-type Ca2+-channels.

  背景：血管收缩是心血管疾病的一个主要病理特征，涉及内皮依赖和独立机制。草酰二唑似乎对各种病症有效。 目的：本研究旨在合成和评估草酰二唑的血管舒张机制：本研究的目的是合成并评估合成的噁二唑衍生物的血管舒张机制。 方法：2,5-二取代的噁二唑衍生物：采用高效简单的方法合成了 2,5-二取代-1,3,4-噁二唑衍生物。研究了这些衍生物对去甲肾上腺素/苯肾上腺素/氯化钾预收缩的完整/脱落内皮大鼠主动脉环的体内外血管舒张作用。 结果：在主动脉环上加入累积浓度的去甲肾上腺素、苯肾上腺素、氯化钾和钙后，OXD-Z2 衍生物可显著拮抗其引起的收缩。在另一项实验中，维拉帕米预处理抑制了去甲肾上腺素和 Ca2+诱导的主动脉收缩，而 OXD-Z2 并未改变维拉帕米诱导的抑制作用。这表明 L 型 Ca2+ 通道在 OXD-Z2 通过抑制钙离子流入诱导的血管舒张中发挥作用。此外，在其他实验中，阿托品（毒蕈碱受体拮抗剂）、L-NAME（NO 合酶抑制剂）和亚甲蓝（非选择性 cGMP 抑制剂）也抑制了 OXD-Z2- 诱导的松弛作用。这些结果表明，OXD-Z2 还能通过激活毒蕈碱受体释放 NO 来介导血管舒张。此外，分子对接研究表明，OXD-Z2 与 L 型 Ca2+ 通道、毒蕈碱（M2）受体和 eNOS 相互作用。 结论：因此，根据上述研究结果推断，OXD-Z2 的血管舒张活性除了直接抑制 L 型 Ca2+ 通道外，还涉及毒蕈碱受体介导的一氧化氮释放。
• Antimycobacterial Evaluation and Microwave-Assisted Synthesis of N-(5-methyl-4-oxo-2-arylthiazolidin-3-yl) Isonicotinamide Derivatives
  作者：Saad Alghamdi、Mazen M. Almehmadi、Mohammad Asif、Mohammed M. Alshehri、Mehnaz Kamal

  DOI：10.1007/s11094-022-02623-0

  日期：2022.5

  Thiazolidinone derivatives represent heterocyclic bioactive compounds. We have synthesized some N-(5-methyl-4-oxo-2-arylthiazolidin-3-yl)-isonicotinamide derivatives (2a–2h) from isoniazid (INH) and screened them as antimycobacterial agents against M. tuberculosis H37Rv strain using microplate alamar blue assay (MABA). Compounds 2a-2h were obtained via cyclocondensation of N-arylideneisonicotinohydrazide derivatives (imine Schiff’s bases) 1a-1h with thiolactic acid. Initial compounds 1a-1h were synthesized by reaction of isoniazid with appropriate benzaldehyde. The structures of title compounds were established by IR, 1H NMR, and mass spectroscopy data. All the title compounds (2a-2h) exhibited antimycobacterial activity and were compared to standard drugs streptomycin (MIC value of 6.25 μg/mL) and isoniazid (MIC value of 3.125 μg/mL). Compound 2g exhibited the highest antimycobacterial activity, but all the tested compounds were less active than standard drugs.

  噻唑烷酮衍生物属于杂环生物活性化合物。我们利用异烟肼（INH）合成了N-(5-甲基-4-氧代-2-芳基噻唑烷-3-基)-异烟酰胺衍生物（2a-2h），并利用微孔板阿拉姆蓝法（MABA）筛选了它们作为抗结核分枝杆菌H37Rv菌株的抗分枝杆菌药物。化合物2a-2h是通过N-芳基亚异烟酰肼衍生物（亚胺-席夫碱）1a-1h与硫代乳酸的环缩合反应得到的。初始化合物1a-1h是通过异烟肼与适当的苯甲醛反应合成的。通过红外光谱、1H核磁共振和质谱数据确定了标题化合物的结构。所有标题化合物（2a-2h）均表现出抗分枝杆菌活性，并与标准药物链霉素（MIC值为6.25μg/mL）和异烟肼（MIC值为3.125μg/mL）进行了比较。化合物2g表现出最高的抗分枝杆菌活性，但所有测试的化合物都比标准药物活性低。