4-aminobenzoic acid N'-(furan-2-ylmethylene)hydrazide | 97742-15-9

• 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: 4-aminobenzoic acid N'-(furan-2-ylmethylene)hydrazide
• 英文别名: 4-amino-N-(furan-2-ylmethylideneamino)benzamide
• CAS: 97742-15-9
• 化学式: C₁₂H₁₁N₃O₂
• 分子量: 229.238
• InChiKey: ZOBRIRJPFNKLQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 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：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  烟酰氯 、 4-aminobenzoic acid N'-(furan-2-ylmethylene)hydrazide 以 乙醚 为溶剂， 反应 24.0h， 以58.7%的产率得到nicotinic acid N-(4-amino-benzoyl)-N'-furan-2-ylmethylenehydrazide
  参考文献：
  名称：

  Synthesis and antitubercular activities of substituted benzoic acid N′-(substituted benzylidene/furan-2-ylmethylene)-N-(pyridine-3-carbonyl)-hydrazides

  摘要：

  A series of benzoic acid hydrazones and its nicotinyl derivatives (1-10) were prepared and evaluated for their antitubercular activity towards a strain of Mycobacterium tuberculosis (MTB). The structures of newly synthesized compounds were confirmed by infrared (IR) and H-1-nuclear magnetic resonance (NMR) spectral data and elemental analysis. The in vitro antitubercular activity of synthesized compounds against MTB was carried out in Middlebrook 7H11agar medium supplemented with OADC by agar dilution method. The antitubercular activity results indicated that nicotinic acid N-(3,5-dinitrobenzoyl)-N'-(4-methoxy-benzylidene)-hydrazide (1) is the most potent among the synthesized compounds with MIC of 3.5 x 10(-3) mu M. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.030
• 作为产物：
  描述：

  苯佐卡因 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4-aminobenzoic acid N'-(furan-2-ylmethylene)hydrazide
  参考文献：
  名称：

  Design and Synthesis of N-Arylphthalimides as Inhibitors of Glucocorticoid-Induced TNF Receptor-Related Protein, Proinflammatory Mediators, and Cytokines in Carrageenan-Induced Lung Inflammation

  摘要：

  N-Arylphthalimides (1-10P) derived from thalidomide by insertion of hydrophobic groups were evaluated for anti-inflammatory activity, and (4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N'-[(4-thoxyphenyl)methylidene]benzohydrazide 6P was identified as a promising anti-inflammatory agent. Further testing confirmed that compared with the control, 6P treatment resulted in a considerable decrease in CD4(+), NF-kappa B p65(+), TNF-alpha(+), IL-6(+), GITR(+), and IL-17(+) cell populations and an increase in the Foxp3(+), CD4(+)Foxp3(+), and I kappa B alpha(+) populations in whold blood and pleural fluid of a mouse model of lung inflammation. Moreover, treatment with compound 6P decreased the proteins associated with inflammation including TNF-alpha, IL-6, IL-17, GITR, NF-kappa B, COX-2, STAT-3, and iNOS and increased the anti-inflammatory mediators such as IL-10 and IL-4. Further, histopathological examination confirmed the potent anti-inflammatory effects of compound 6P. Thus, the N-arylphthalimide derivative 6P acts as a potent anti-inflammatory agent in the carrageenan-induced lung inflammation model, suggesting that this compound may be useful for the treatment of inflammation in a clinical setting.

  DOI：

  10.1021/acs.jmedchem.5b00934

文献信息

• Synthesis and Investigation of Antimicrobial Activity of Some Nifuroxazide Analogues
  作者：Huda S. Alsaeedi、Nabila A. Aljaber、Ismet Ara

  DOI：10.14233/ajchem.2015.18896

  日期：——

  A series of nifuroxazide analogues [(2a-2e)-(10a-10f)] have been synthesized, structurally identified and tested for antimicrobial activity against a panel of bacteria (Gram-positive and Gram-negative) and the yeast-like pathogenic fungus Candida albicans. The most active compound in this series was 4-amino-benzoic acid (5-nitro-furan-2-ylmethylene)-hydrazide (2b) and 2-amino-benzoic acid (5-nitro-furan-2-ylmethylene)-hydrazide (2d). Furthermore, compounds (9a-9g) and (10a-10g) recorded no activity against selected species except compounds (9f) and (10f) suggesting that using furoic hydrazide and the corresponding hydrazide of thiophene did not improve the antimicrobial activities for this type of compounds. Regarding the activity against Candida albicans, all compounds showed no activity with an exception of substituted nitro furan (2a-2d).

  一系列硝呋醛酰肼类衍生物[(2a-2e)-(10a-10f)]已被合成、结构鉴定，并测试了其对一组细菌（革兰氏阳性和革兰氏阴性）和类酵母致病真菌白色念珠菌的抗微生物活性。在这一系列化合物中，活性最高的为4-氨基苯甲酸（5-硝基呋喃-2-亚甲基）酰肼（2b）和2-氨基苯甲酸（5-硝基呋喃-2-亚甲基）酰肼（2d）。此外，化合物（9a-9g）和（10a-10g）对选定物种无活性，除了化合物（9f）和（10f），这表明使用呋喃酰肼及其对应的噻吩酰肼并未提高此类化合物的抗菌活性。对于对白色念珠菌的活性，所有化合物均无活性，除了取代的硝基呋喃（2a-2d）。
• Design and Synthesis of <i>N</i>-Arylphthalimides as Inhibitors of Glucocorticoid-Induced TNF Receptor-Related Protein, Proinflammatory Mediators, and Cytokines in Carrageenan-Induced Lung Inflammation
  作者：Mashooq A. Bhat、Mohamed A. Al-Omar、Mushtaq A. Ansari、Khairy M. A. Zoheir、Faisal Imam、Sabry M. Attia、Saleh A. Bakheet、Ahmed Nadeem、Hesham M. Korashy、Andrey Voronkov、Vladimir Berishvili、Sheikh F. Ahmad

  DOI：10.1021/acs.jmedchem.5b00934

  日期：2015.11.25

  N-Arylphthalimides (1-10P) derived from thalidomide by insertion of hydrophobic groups were evaluated for anti-inflammatory activity, and (4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N'-[(4-thoxyphenyl)methylidene]benzohydrazide 6P was identified as a promising anti-inflammatory agent. Further testing confirmed that compared with the control, 6P treatment resulted in a considerable decrease in CD4(+), NF-kappa B p65(+), TNF-alpha(+), IL-6(+), GITR(+), and IL-17(+) cell populations and an increase in the Foxp3(+), CD4(+)Foxp3(+), and I kappa B alpha(+) populations in whold blood and pleural fluid of a mouse model of lung inflammation. Moreover, treatment with compound 6P decreased the proteins associated with inflammation including TNF-alpha, IL-6, IL-17, GITR, NF-kappa B, COX-2, STAT-3, and iNOS and increased the anti-inflammatory mediators such as IL-10 and IL-4. Further, histopathological examination confirmed the potent anti-inflammatory effects of compound 6P. Thus, the N-arylphthalimide derivative 6P acts as a potent anti-inflammatory agent in the carrageenan-induced lung inflammation model, suggesting that this compound may be useful for the treatment of inflammation in a clinical setting.
• Synthesis and antitubercular activities of substituted benzoic acid N′-(substituted benzylidene/furan-2-ylmethylene)-N-(pyridine-3-carbonyl)-hydrazides
  作者：Pradeep Kumar、Balasubramanian Narasimhan、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.ejmech.2010.08.030

  日期：2010.12

  A series of benzoic acid hydrazones and its nicotinyl derivatives (1-10) were prepared and evaluated for their antitubercular activity towards a strain of Mycobacterium tuberculosis (MTB). The structures of newly synthesized compounds were confirmed by infrared (IR) and H-1-nuclear magnetic resonance (NMR) spectral data and elemental analysis. The in vitro antitubercular activity of synthesized compounds against MTB was carried out in Middlebrook 7H11agar medium supplemented with OADC by agar dilution method. The antitubercular activity results indicated that nicotinic acid N-(3,5-dinitrobenzoyl)-N'-(4-methoxy-benzylidene)-hydrazide (1) is the most potent among the synthesized compounds with MIC of 3.5 x 10(-3) mu M. (C) 2010 Elsevier Masson SAS. All rights reserved.