4-chloro-N'-[(1E)-4-hydroxy-3-methoxyphenylmethylidene]benzohydrazide | 1355449-30-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-chloro-N'-[(1E)-4-hydroxy-3-methoxyphenylmethylidene]benzohydrazide
• 英文别名: (E)-4chloro-N-(4-hydroxy-3-methoxybenzylidene)benzohydrazide；4-chloro-N'-(4-hydroxy-3-methoxybenzylidene)benzohydrazide；4-chloro-N'-[(E)-(4-hydroxy-3-methoxyphenyl)methylidene]benzohydrazide；4-chloro-N-[(E)-(4-hydroxy-3-methoxyphenyl)methylideneamino]benzamide
• CAS: 1355449-30-7
• 化学式: C₁₅H₁₃ClN₂O₃
• 分子量: 304.733
• InChiKey: YKJREGSLFZIFLE-RQZCQDPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  70.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯苯甲酸乙酯 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 4.5h， 生成 4-chloro-N'-[(1E)-4-hydroxy-3-methoxyphenylmethylidene]benzohydrazide
  参考文献：
  名称：

  Design, characterization, computational studies, and pharmacological evaluation of substituted-N′-[(1E) substituted-phenylmethylidene]benzohydrazide analogs

  摘要：

  A series of substituted-N'-[(1E)-substituted-phenylmethylidene]benzohydrazide analogs were synthesized and authenticated by TLC, UV-Visible, FTIR, and NMR spectroscopic techniques. The physicochemical similarity of the new analogs with standard drugs was assessed by calculating from a set of ten physicochemical properties using software programs. The information so obtained can be related to prediction of biological activity for important targets. All the target compounds 4a-n were evaluated for their antioxidant, anti-inflammatory, and antimicrobial activity using different in vitro models. The test compounds demonstrated good similarity values with respect to the standard drugs. The compounds 4c, 4d, and 4e have emerged as important lead compounds showing potential anti-inflammatory; and 4b, 4f, and 4c having antioxidant profile. While studying MIC against bacterial strains 4c, 4f, 4i, 4k, and 4m were most active among all the target compounds. All compounds were found to have very good antifungal activity. The compounds having nitro substitution at the arylidene moiety i.e., 4c and 4f showed the most potent antifungal as well as antibacterial activities. While studying total antioxidant activity, all target compounds were found to have good antioxidant activity.

  DOI：

  10.1007/s00044-012-0270-0

文献信息

• Synthesis and radical scavenging activity of new phenolic hydrazone/hydrazide derivatives: Experimental and theoretical studies
  作者：Houssem Boulebd、Yasmine Zine、Imene Amine Khodja、Arif Mermer、Adem Demir、Abdelmadjid Debache

  DOI：10.1016/j.molstruc.2021.131546

  日期：2022.2

  than their analogs hydrazone-hydrazide 6–10 via the main antiradical mechanism as well as toward DPPH and ABTS radicals. The NH group of the hydrazone is more reactive than the NH group of the hydrazide and the phenolic OH groups. The carbonyl group of the hydrazide plays a negative role in the antiradical activity of such molecules. Among the studied compounds, compound 4 was found to be the best radical

  腙和基于腙-酰肼的化合物代表了重要类别的化合物，由于其不同的药理作用，这些化合物继续引起越来越多的兴趣。在本研究中，一系列新的酚腙/酰肼衍生物 ( 1-10 ) 已成功合成，并使用实验和理论方法评估了它们的抗自由基活性。腙1-5被认为是比显著它们的类似物腙肼更具反应性6-10 通过主要的抗自由基机制以及针对 DPPH 和 ABTS 自由基。腙的NH基团比酰肼的NH基团和酚OH基团更具反应性。酰肼的羰基在此类分子的抗自由基活性中起负面作用。在所研究的化合物中，发现化合物4是最好的自由基清除剂，其 SC 50值（导致 DPPH 或 ABST 清除的 50% 的浓度）与抗坏血酸和 Trolox 的值相当。这些发现为腙和腙-酰肼类化合物的构效关系提供了见解，并为开发新型强效抗氧化剂开辟了新的视角。
• Synthesis and Crystal Structures of 4-Chloro-N′-(4-hydroxy-3-nitrobenzylidene)benzohydrazide monohydrate and 4-Chloro-N′-(4-hydroxy-3-methoxybenzylidene)benzohydrazide monohydrate
  作者：Yan Lei、Ting-Zhen Li、Chuan Fu、Xiao-Lin Guan、Yao Tan

  DOI：10.1007/s10870-011-0161-0

  日期：2011.11

  Two new hydrazone compounds, 4-chloro-N′-(4-hydroxy-3-nitrobenzylidene)benzohydrazide monohydrate (1) and 4-chloro-N′-(4-hydroxy-3-methoxybenzylidene)benzohydrazide monohydrate (2), were synthesized and characterized by physico-chemical methods and single crystal X-ray diffraction. Compound 1 crystallizes in the monoclinic space group P21/c with unit cell parameters a = 23.257(3) Å, b = 4.829(1) Å, c = 12.763(2) Å, β = 96.017(2)°, V = 1425.5(5) Å3, Z = 4, R 1 = 0.0525, and wR 2 = 0.1120. Compound 2 crystallizes in the monoclinic space group P21/c with unit cell parameters a = 8.103(3) Å, b = 21.321(3) Å, c = 10.594(3) Å, β = 120.281(2)°, V = 1580.5(8) Å3, Z = 4, R 1 = 0.0480, and wR 2 = 0.1078. Both compounds contains a hydrazone molecule and a water molecule. The crystals of the compounds are stabilized by N–H···O, O–H···O, and O–H···N hydrogen bonds. Two new hydrazone compounds have been synthesized and characterized by physico-chemical methods and single crystal X-ray diffraction.

  通过物理化学方法和单晶 X 射线衍射，合成了两种新的腙类化合物：4-氯-N′-(4-羟基-3-亚硝基苄基)苯并肼一水合物 (1) 和 4-氯-N′-(4-羟基-3-甲氧基亚苄基)苯并肼一水合物 (2)。化合物 1 结晶于单斜空间群 P21/c，单胞参数 a = 23.257(3) Å，b = 4.829(1) Å，c = 12.763(2) Å, β = 96.017(2)°, V = 1425.5(5) Å3, Z = 4, R 1 = 0.0525, and wR 2 = 0.1120.化合物 2 在单斜空间群 P21/c 中结晶，单胞参数 a = 8.103(3) Å，b = 21.321(3) Å，c = 10.594(3) Å, β = 120.281(2)°, V = 1580.5(8) Å3, Z = 4, R 1 = 0.0480, and wR 2 = 0.1078.这两种化合物都含有一个腙分子和一个水分子。化合物的晶体通过 N-H--O、O-H--O 和 O-H-N 氢键而稳定。我们合成了两种新的腙化合物，并用物理化学方法和单晶 X 射线衍射法对其进行了表征。
• Design, characterization, computational studies, and pharmacological evaluation of substituted-N′-[(1E) substituted-phenylmethylidene]benzohydrazide analogs
  作者：Suman Bala、Goldie Uppal、Sunil Kamboj、Vipin Saini、D. N. Prasad

  DOI：10.1007/s00044-012-0270-0

  日期：2013.6

  A series of substituted-N'-[(1E)-substituted-phenylmethylidene]benzohydrazide analogs were synthesized and authenticated by TLC, UV-Visible, FTIR, and NMR spectroscopic techniques. The physicochemical similarity of the new analogs with standard drugs was assessed by calculating from a set of ten physicochemical properties using software programs. The information so obtained can be related to prediction of biological activity for important targets. All the target compounds 4a-n were evaluated for their antioxidant, anti-inflammatory, and antimicrobial activity using different in vitro models. The test compounds demonstrated good similarity values with respect to the standard drugs. The compounds 4c, 4d, and 4e have emerged as important lead compounds showing potential anti-inflammatory; and 4b, 4f, and 4c having antioxidant profile. While studying MIC against bacterial strains 4c, 4f, 4i, 4k, and 4m were most active among all the target compounds. All compounds were found to have very good antifungal activity. The compounds having nitro substitution at the arylidene moiety i.e., 4c and 4f showed the most potent antifungal as well as antibacterial activities. While studying total antioxidant activity, all target compounds were found to have good antioxidant activity.