N’-(4-fluorobenzylidene)isonicotinohydrazide | 86189-87-9

• 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-fluorobenzylidene)isonicotinohydrazide
• 英文别名: N'-(4-fluorobenzylidene)isonicotinohydrazide；N-[(4-fluorophenyl)methylideneamino]pyridine-4-carboxamide
• CAS: 86189-87-9
• 化学式: C₁₃H₁₀FN₃O
• mdl: MFCD00498476
• 分子量: 243.24
• InChiKey: SVYYQPLGBPBEQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：

  N’-(4-fluorobenzylidene)isonicotinohydrazide 在 sodium iodide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 9.0h， 生成 4-(2-(4-fluorobenzylidene)hydrazinecarbonyl)-1-(4-phenoxybutyl)pyridin-1-ium tetrafluoroborate
  参考文献：
  名称：

  绿色超声与常规合成和特定任务吡啶离子液体腙束缚氟化反阴离子的表征：真菌麦角甾醇生物合成的新型抑制剂。

  摘要：

  设计了一系列基于吡啶鎓腙支架并结合六氟磷酸盐 (PF₆-)、四氟硼 (BF₄) 和/或三氟乙酸盐 (CF₃COO-) 抗衡阴离子的特定任务离子液体 (IL)，并通过 IR、NMR 和质谱进行表征。光谱测定法。反应在常规和绿色超声程序下进行。研究了合成化合物 2-25 针对 40 种念珠菌菌株（4 种标准分离株和 36 种临床分离株）的抗真菌潜力。对于标准和口服念珠菌分离株，合成化合物的最低抑制浓度 (MIC90) 均在 62.5-2000 μg/mL 范围内。MIC90 结果表明，合成的 1-(2-(4-氯苯基)-2-氧代乙基)-4-(2-(4-氟亚苄基)肼羰基)-吡啶-1-鎓六氟磷酸盐 (11) 被发现最有效，然后是 4-(2-(4-氟亚苄基)肼羰基)-1-(2-(4-硝基苯基)-2-氧代乙基)-吡啶-1-鎓六氟磷酸盐 (14) 和 1-(2-乙氧基-2) -氧代乙基)-4-(2-(4-

  DOI：

  10.3390/molecules22111532
• 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-fluorobenzylidene)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

• Design, synthesis, characterization, cytotoxic and structure activity relationships of novel Ru(II) complexes
  作者：Sreekanth Thota、Srujana Vallala、Rajeshwar Yerra、Eliezer J. Barreiro

  DOI：10.1016/j.cclet.2015.03.011

  日期：2015.6

  containing complexes have long been known to be well suited for biological applications, and have long been utilized as replacements to popular platinum based-drugs. Here, we report a novel series of ruthenium(II) arene compounds bearing thiosemicarbazone and isonicotinylhydrazone ligands with potent anticancer activity their structure activity relationships and apoptosis was studied. The cytotoxic activity

  含铂化合物已显示出抗肿瘤潜力，但其临床应用受到高毒性的限制。长期以来，众所周知，含钌的配合物非常适合生物应用，并已长期用作流行的铂基药物的替代品。在这里，我们报告一系列新型的钌（II）芳烃化合物，带有硫代半脲和异烟酰ot配体，具有强大的抗癌活性，研究了它们的结构活性关系和细胞凋亡。新的钌（II）芳烃化合物的细胞毒活性已在几种细胞系（Molt 4 / C 8，L1210，CEM，HL60和BEL7402）中进行了评估。其中，有十种复合物在体外具有优异的表现IC 50在亚微摩尔范围内，对各种细胞系具有抑制生长的活性。
• 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。
• SYNTHESIS OF SOME 2,3-DIHYDRO-1,3,4-OXADIAZOLES AND 4,5-DIHYDRO-1,2,4-TRIAZOLES AS ANTICANCER AGENTS
  作者：TAWFEEK A. YAHYA、JALAL H. ABDULLAH

  DOI：10.22159/ijpps.2020v12i8.36508

  日期：——

  Objective: The main objective of this work was to synthesize and evaluate the novel 2,3-dihydro-1,3,4-oxadiazole and 4,5-dihydro-1,2,4-triazole derivatives for cytotoxic activities. Methods: The 2,3-dihydro-1,3,4-oxadiazole derivatives 4a-h were synthesized by cyclization of N'-(substituted-benzylidene) isonicotinohydrazide 3a-e in refluxing acetic anhydride. The 2,3-dihydro-1,3,4-oxadiazole derivatives 4a-h were converted into the corresponding 4,5-dihydro-1,2,4-triazoles 5a-h using ammonia. All the synthesized compounds were identified, depending on the physical and spectral data. Title compounds were assessed for their cytotoxic activity against human cancer cell line (MCF-7) by using Sulforhodamine B (SRB) colorimetric assay. Results: All the synthesized compounds showed characteristic peaks in FTIR, 1HNMR and Mass spectral analysis. The results of the in vitro cytotoxic activity revealed that the compound 4c exhibited equipotent cytotoxic activity with an IC50 value of 8.04 µM when compared with that of standard drug doxorubicin (IC50= 8.02 µM). The reminder compounds have shown good to moderate cytotoxic activities when compared with that of a reference standard. Conclusion: We synthesized a series of title compounds in quantitative yields. Most derivatives showed moderate to good cytotoxic activity.  

  目的：本研究的主要目的是合成和评价新型的2,3-二氢-1,3,4-噁二唑和4,5-二氢-1,2,4-三唑衍生物的细胞毒活性。 方法：通过在回流乙酸酐中环化N'-(取代苯基亚甲基)异烟肼酰肼3a-e，合成了2,3-二氢-1,3,4-噁二唑衍生物4a-h。将2,3-二氢-1,3,4-噁二唑衍生物4a-h转化为相应的4,5-二氢-1,2,4-三唑5a-h，使用氨水。根据物理和光谱数据鉴定了所有合成的化合物。使用Sulforhodamine B（SRB）比色法，评估了标题化合物对人类癌细胞系（MCF-7）的细胞毒活性。 结果：所有合成的化合物在FTIR，1HNMR和质谱分析中显示出特征峰。体外细胞毒活性的结果表明，化合物4c与标准药物多柔比星（IC50 = 8.02 µM）相比，表现出等效的细胞毒活性，其IC50值为8.04 µM。其他化合物与参考标准相比，显示出良好至中等的细胞毒活性。 结论：我们以定量收率合成了一系列标题化合物。大多数衍生物表现出中等至良好的细胞毒活性。
• 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; Basile; Zappala, Il Farmaco, 1992, vol. 47, # 6, p. 893 - 906
  作者：Vigorita、Basile、Zappala、Gabrielli、Pizzimenti

  DOI：——

  日期：——