2-(2-(4-nitrophenyl)hydrazono)-3-oxo-3-phenylpropanal

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-(4-nitrophenyl)hydrazono)-3-oxo-3-phenylpropanal
• 英文别名: 2-[(4-nitrophenyl)hydrazono]-3-oxo-3-phenylpropanal；2-[(4-nitrophenyl)hydrazinylidene]-3-oxo-3-phenylpropanal
• 化学式: C₁₅H₁₁N₃O₄
• 分子量: 297.27
• InChiKey: BWECMERHDXIXSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101.67
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(2-(4-nitrophenyl)hydrazono)-3-oxo-3-phenylpropanal 在 硫酸 作用下， 反应 0.08h， 以50%的产率得到3-benzoyl-6-nitrocinnoline
  参考文献：
  名称：

  从芳基甲基酮高效合成3-芳基肉桂啉

  摘要：

  描述了从合适的芳基甲基酮开始的3-芳基肉桂啉的有效合成。将后者分两步转化为相应的3-氧代-3-芳基-2-芳基肼基丙醛，其在浓盐酸中经酸催化环化。硫酸或多磷酸（PPA）生成相应的3-aroylcinnolines。

  DOI：

  10.1016/s0040-4020(00)01141-8
• 作为产物：
  描述：

  苯乙酮 在 盐酸 、 sodium nitrite 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 水 为溶剂， 反应 1.25h， 生成 2-(2-(4-nitrophenyl)hydrazono)-3-oxo-3-phenylpropanal
  参考文献：
  名称：

  Indeno[1,2‐b]pyridin‐5‐one derivatives containing azo groups and their hydrazonal precursors: Synthesis, antimicrobial profile, DNA gyrase binding affinity, and molecular docking

  摘要：

  摘要 对许多抗生素具有抗药性的病菌在全世界迅速增加。一大批研究人员正在积极寻找更好的药物。在此，我们设计了两个带有腙和偶氮基团的肼基和茚并[1,2-b]吡啶-5-酮系列，以测试它们的抗菌活性。根据光谱数据和元素分析，确定了所有衍生物的分子结构。测试的腙和偶氮化合物的抗菌活性结果表明，几种衍生物具有很好的潜力。腙 4a-h 和腙 6a-g 的最低抑菌浓度 (MIC) 在 3.91-250 μg/mL 范围内显示出良好的抗菌活性，在 15.6-500 μg/mL 范围内显示出中等的抗真菌活性。最有前景的腙 4f 和偶氮化合物 6a 对粪链球菌和大肠杆菌的 MIC 值分别为 3.91 和 7.81 μg/mL。此外，偶氮化合物 6a 对肠杆菌的 MIC 值为 3.91 μg/mL。此外，衍生物 4f 对大肠杆菌回旋酶 A 酶具有显著的抑制作用（IC50 = 5.53 μg/mL）。另一方面，与化合物 4f 和参考标准药物新生物素（IC50 分别为 5.53 和 1.88 μg/mL）相比，化合物 6a（IC50 为 14.05 μg/mL）的 DNA 回旋酶抑制活性最低。计算了最有前景的两个分子 4f 和 6a 的药代动力学和药效学特征，并进行了分子对接研究，结果表明这两个化合物具有良好的 ADME 特征，与 DNA gyrase 结合位点的结合亲和力高。

  DOI：

  10.1002/jhet.4759

文献信息

• Maturation of Murine Bone Marrow-Derived Dendritic Cells Induced by Radix Glycyrrhizae Polysaccharide
  作者：Xiaobing Li、Xiaojuan He、Biao Liu、Li Xu、Cheng Lu、Hongyan Zhao、Xuyan Niu、Shilin Chen、Aiping Lu

  DOI：10.3390/molecules17066557

  日期：——

  Radix Glycyrrhizae polysaccharide (GP), the most important component of Radix Glycyrrhizae, has been reported to have many immunopharmacological activities. However, the mechanism by which GP affects dendritic cells (DCs) has not been elucidated. In this study, we investigated the effect of GP on murine bone marrow-derived DCs and the potential pathway through which GP exerts this effect. Mononuclear cells (MNCs) were isolated from murine bone marrow and induced to become DCs by culturing with GM-CSF and IL-4. Six days later, DCs were divided into three groups: control group, GP group and LPS group. After 48 h of treatment, phenotypic figures and antigen uptake ability were determined by FACS analysis. The proliferation of DC-stimulated allogenic CD3+ T cells was detected by WST-1. IL-12 p70 and IFN-γ, which are secreted by DCs and CD3+ T cells respectively, were quantified by ELISA. Additionally, IL-12 p40 mRNA expression was determined by real-time PCR. Alterations in TLR4-related signaling pathways were examined by performing an antibody neutralization experiment. Treatment of DCs with GP resulted in the enhanced expression of the cell surface molecules CD80, CD86 and MHC I-A/I-E. GP also increased the production of IL-12 p70 by DCs in a time-dependent manner. The endocytosis of FITC-dextran by DCs was suppressed by GP administration. Furthermore, GP-treated DCs enhanced both the proliferation and IFN-γ secretion of allogenic CD3+ T cells. Finally, the effects of GP on DCs were partially reduced by using inhibitors of TLR4, NF-κB, p38 MAPK or JNK. In conclusion, GP can induce the maturation of DCs, and does so, in part, by regulating a TLR4-related signaling pathway.

  据报道，甘草多糖（GP）是甘草中最重要的成分，具有多种免疫药理活性。然而，GP 影响树突状细胞（DCs）的机制尚未阐明。在这项研究中，我们调查了 GP 对小鼠骨髓衍生 DC 的影响以及 GP 发挥这种作用的潜在途径。从小鼠骨髓中分离出单核细胞（MNCs），用 GM-CSF 和 IL-4 培养诱导其成为 DCs。六天后，DCs 被分为三组：对照组、GP 组和 LPS 组。处理 48 小时后，通过 FACS 分析测定表型和抗原摄取能力。用 WST-1 检测 DC 刺激的异源 CD3+ T 细胞的增殖情况。IL-12 p70和IFN-γ分别由DC和CD3+ T细胞分泌，通过ELISA进行定量。此外，IL-12 p40 mRNA 的表达也通过实时 PCR 进行了测定。通过抗体中和实验检测了 TLR4 相关信号通路的变化。用 GP 处理 DC 会导致细胞表面分子 CD80、CD86 和 MHC I-A/I-E 的表达增强。GP 还以时间依赖性的方式增加了直流细胞产生的 IL-12 p70。GP能抑制DC对FITC-葡聚糖的内吞。此外，GP 处理的 DC 还能增强异源 CD3+ T 细胞的增殖和 IFN-γ 分泌。最后，使用 TLR4、NF-κB、p38 MAPK 或 JNK 抑制剂可部分降低 GP 对 DC 的影响。总之，GP 可诱导 DCs 成熟，而且部分是通过调节与 TLR4 相关的信号通路来实现的。
• High-Pressure Metal-Free Catalyzed One-Pot Two-Component Synthetic Approach for New 5-Arylazopyrazolo[3,4-b]Pyridine Derivatives
  作者：AbdElAziz A. Nayl、Hamada Mohamed Ibrahim、Kamal M. Dawood、Wael A. A. Arafa、Ahmed I. Abd-Elhamid、Ismail M. Ahmed、Mohamed A. Abdelgawad、Hazim M. Ali、Ibrahim Hotan Alsohaimi、Ashraf A. Aly、Stefan Bräse、Asmaa Kamal Mourad

  DOI：10.3390/molecules27196369

  日期：——

  An appropriate and efficient Q-tube-assisted ammonium acetate-mediated protocol for the assembly of the hitherto unreported 5-arylazopyrazolo[3,4-b]pyridines was demonstrated. This methodology comprises the cyclocondensation reaction of 5-amino-2-phenyl-4H-pyrazol-3-one with an assortment of arylhydrazonals in an NH4OAc/AcOH buffer solution operating a Q-tube reactor. This versatile protocol exhibited

  证明了一种合适且有效的 Q 管辅助乙酸铵介导的方案，用于组装迄今为止未报道的 5-芳基吡唑并[3,4- b ] 吡啶。该方法包括 5-氨基-2-苯基-4 H-吡唑-3-酮与各种芳基腙醛在 NH 4中的环缩合反应操作 Q 管反应器的 OAc/AcOH 缓冲溶液。这种多功能协议具有几个突出的优点：易于处理、条件温和、可扩展、底物范围广、安全（Q-tube 套件仅用于压制和密封）和高原子经济性。因此，与常规条件相比，在高压下进行此类反应并利用 Q 管反应器似乎更适合获得所需的产品。应用多种光谱方法和 X 射线单晶技术来确认目标化合物的拟议结构。
• Reactions under Pressure: Synthesis of Functionally Substituted Arylhydrazonal Derivatives as Precursors of Novel Pyridazines and Nicotinates
  作者：K. M. Al Zaydi、M. A. Al-Johani、N. F. Alqahtani、S. M. Mousally、N. Hilmy Elnagdi

  DOI：10.1134/s1070363220040234

  日期：2020.4

  Q-tube assisted multicomponent synthesis of novel arylhydrazonals, pyridazines and nicotinates has been explored. The target molecules have been prepared via one pot reaction of arylhydrazonals with activated methylene nitriles in either ethanolic piperidine, dimethyl acetylene dicarboxylate (DMAD), 1,4-diazobicyclo[2.2.2]octane (DABCO), or Ph3P under pressure. Such conditions make reaction time much shorter and yields higher as compared with those conducted under conventional conditions. The structures of products have been determined by X-ray crystallography and spectroscopic methods.
• Efficient synthesis of 3-aroylcinnolines from aryl methyl ketones
  作者：Nouria A Al-Awadi、Mohamed Hilmy Elnagdi、Yehia A Ibrahim、Kamini Kaul、Ajith Kumar

  DOI：10.1016/s0040-4020(00)01141-8

  日期：2001.2

  An efficient synthesis of 3-aroylcinnolines starting from the appropriate aryl methyl ketones is described. The latter were converted in two steps to the corresponding 3-oxo-3-aryl-2-arylhydrazonopropanals, which upon acid catalyzed cyclization in conc. sulfuric acid or polyphosphoric acid (PPA) led to the corresponding 3-aroylcinnolines.

  描述了从合适的芳基甲基酮开始的3-芳基肉桂啉的有效合成。将后者分两步转化为相应的3-氧代-3-芳基-2-芳基肼基丙醛，其在浓盐酸中经酸催化环化。硫酸或多磷酸（PPA）生成相应的3-aroylcinnolines。
• Indeno[1,2‐<i>b</i>]pyridin‐5‐one derivatives containing azo groups and their hydrazonal precursors: Synthesis, antimicrobial profile, <scp>DNA</scp> gyrase binding affinity, and molecular docking
  作者：Refaie M. Kassab、Zeinab A. Muhammad、Sami A. Al‐Hussain、Magdi E. A. Zaki、Mona H. Ibrahim、Amani M. R. Alsaedi、Thoraya A. Farghaly

  DOI：10.1002/jhet.4759

  日期：2024.2

  The prevalence of germs that are resistant to many antibiotics is rising rapidly the world over. There is a large group of researchers actively looking for better medicines. Here, we designed two series of hydrazonal and indeno[1,2‐b]pyridin‐5‐one bearing hydrazone and azo‐groups to test their antimicrobial activity. Molecular structures of all derivatives were assured based on their spectral data and elemental analyses. Results of the antimicrobial activity of the tested hydrazone and azo compounds showed promising potential for several derivatives. The minimum inhibitory concentrations (MICs) of hydrazones 4a‐h and 6a‐g displayed good antibacterial reactivities with a range of 3.91–250 μg/mL and moderate antifungal activity with a range of 15.6–500 μg/mL. The most promising hydrazone 4f and azo‐6a compounds demonstrated MIC values against Streptococcus faecalis and Escherichia coli equal to 3.91 and 7.81 μg/mL, respectively. Moreover, azo compound 6a showed MIC value equal to 3.91 μg/mL against Enterobacter cloacae species. Additionally, derivative 4f exhibited a significant inhibitory profile against the E. coli gyrase A enzyme (IC₅₀ = 5.53 μg/mL). On the other hand, compound 6a (IC₅₀ 14.05 μg/mL) exhibited the lowest DNA gyrase inhibitory activity as compared to compounds 4f and reference standard drug novobiocin, IC₅₀ 5.53 and 1.88 μg/mL, respectively. Pharmacokinetic and pharmacodynamic profiles and molecular docking studies for the two most promising molecules 4f and 6a were computed and revealed that both compounds have good ADME profiles and high binding affinity to DNA gyrase binding site.

  摘要 对许多抗生素具有抗药性的病菌在全世界迅速增加。一大批研究人员正在积极寻找更好的药物。在此，我们设计了两个带有腙和偶氮基团的肼基和茚并[1,2-b]吡啶-5-酮系列，以测试它们的抗菌活性。根据光谱数据和元素分析，确定了所有衍生物的分子结构。测试的腙和偶氮化合物的抗菌活性结果表明，几种衍生物具有很好的潜力。腙 4a-h 和腙 6a-g 的最低抑菌浓度 (MIC) 在 3.91-250 μg/mL 范围内显示出良好的抗菌活性，在 15.6-500 μg/mL 范围内显示出中等的抗真菌活性。最有前景的腙 4f 和偶氮化合物 6a 对粪链球菌和大肠杆菌的 MIC 值分别为 3.91 和 7.81 μg/mL。此外，偶氮化合物 6a 对肠杆菌的 MIC 值为 3.91 μg/mL。此外，衍生物 4f 对大肠杆菌回旋酶 A 酶具有显著的抑制作用（IC50 = 5.53 μg/mL）。另一方面，与化合物 4f 和参考标准药物新生物素（IC50 分别为 5.53 和 1.88 μg/mL）相比，化合物 6a（IC50 为 14.05 μg/mL）的 DNA 回旋酶抑制活性最低。计算了最有前景的两个分子 4f 和 6a 的药代动力学和药效学特征，并进行了分子对接研究，结果表明这两个化合物具有良好的 ADME 特征，与 DNA gyrase 结合位点的结合亲和力高。