4-amino-benzoic acid-(3-nitro-benzylidenehydrazide) | 35559-21-8

• 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-amino-benzoic acid-(3-nitro-benzylidenehydrazide)
• 英文别名: 4-Amino-benzoesaeure-(3-nitro-benzylidenhydrazid)；4-Aminobenzoic acid 2-[(3-nitrophenyl)methylene]hydrazide；4-amino-N-[(3-nitrophenyl)methylideneamino]benzamide
• CAS: 35559-21-8
• 化学式: C₁₄H₁₂N₄O₃
• mdl: MFCD00416740
• 分子量: 284.274
• InChiKey: PTTMHDPDUZCXFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 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：
  113
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  烟酰氯 、 4-amino-benzoic acid-(3-nitro-benzylidenehydrazide) 以 乙醚 为溶剂， 反应 24.0h， 以38%的产率得到N-(4-aminobenzoyl)-N-[(3-nitrophenyl)methylideneamino]pyridine-3-carboxamide
  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-amino-benzoic acid-(3-nitro-benzylidenehydrazide)
  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

• Hansch analysis of substituted benzoic acid benzylidene/furan-2-yl-methylene hydrazides as antimicrobial agents
  作者：Pradeep Kumar、Balasubramanian Narasimhan、Deepika Sharma、Vikramjeet Judge、Rakesh Narang

  DOI：10.1016/j.ejmech.2008.10.034

  日期：2009.5

  antimicrobial activity of substituted hydrazides. To understand the relationship between physicochemical parameters and antimicrobial activity of substituted hydrazide derivatives, QSAR investigation was performed by the development of one-target and multi-target models. The multi-target model was found to be effective in describing the antimicrobial activity of substituted hydrazides in comparison to the

  合成了一系列取代的酰肼衍生物，并对其进行了体外筛选对五种代表性微生物的抗菌活性。抗菌研究的结果表明，苯甲酸部分上吸电子基团的存在提高了抗菌活性。此外，杂环呋喃的存在不能改善取代的酰肼的抗微生物活性。为了解取代酰肼衍生物的理化参数与抗菌活性之间的关系，通过开发一靶标和多靶标模型进行了QSAR研究。与单靶标模型相比，发现多靶标模型可有效描述取代的酰肼的抗菌活性。此外，它还表明了拓扑参数，价三阶分子连接指数（3 χ v）和电子参数，最高能量在描述被取代的酰肼的抗微生物活性占据分子轨道（HOMO）。
• Colautti,A. et al., Chimica Therapeutica, 1971, vol. 6, p. 367 - 379
  作者：Colautti,A. et al.

  DOI：——

  日期：——
• Mechanistic differences between in vitro assays for hydrazone-based small molecule inhibitors of anthrax lethal factor
  作者：M. Leslie Hanna、Theodore M. Tarasow、Julie Perkins

  DOI：10.1016/j.bioorg.2006.07.004

  日期：2007.2

  A systematically generated series of hydrazones were analyzed as potential inhibitors of anthrax lethal factor. The hydrazones were screened using one UV-based and two fluorescence-based in vitro assays. The study identified several inhibitors with IC50 values in the micromolar range, and importantly, significant differences in the types of inhibition were observed with the different assays. (c) 2006 Elsevier Inc. All rights reserved.
• Jani; Undavia; Trivedi, Journal of the Indian Chemical Society, 1990, vol. 67, # 7, p. 601 - 602
  作者：Jani、Undavia、Trivedi

  DOI：——

  日期：——
• Patel; dave; Langalia, Journal of the Indian Chemical Society, 1984, vol. 61, # 8, p. 718 - 720
  作者：Patel、dave、Langalia、Thaker

  DOI：——

  日期：——