2-methoxy-N'-(pyridin-4-methylene)benzohydrazide | 109352-30-9

• 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: 2-methoxy-N'-(pyridin-4-methylene)benzohydrazide
• 英文别名: 2-methoxy-N-(pyridin-4-ylmethylideneamino)benzamide
• CAS: 109352-30-9
• 化学式: C₁₄H₁₃N₃O₂
• mdl: MFCD01202413
• 分子量: 255.276
• InChiKey: YJJQQKUOKBHHRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 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：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲氧基苯甲酸甲酯 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成 2-methoxy-N'-(pyridin-4-methylene)benzohydrazide
  参考文献：
  名称：

  Synthesis of 2-methoxybenzoylhydrazone and evaluation of their antileishmanial activity

  摘要：

  Compounds 1-25 showed varying degree of antileishmanial activities with IC50 values ranging between 1.95 and 88.56 mu M. Compounds 2, 10, and 11 (IC50 = 3.29 +/- 0.07 mu M, 1.95 +/- 0.04 mu M, and 2.49 +/- 0.03 mu M, respectively) were found to be more active than standard pentamidine (IC50 = 5.09 +/- 0.04 mu M). Compounds 7 (IC50 = 7.64 +/- 0.1 mu M), 8 (IC50 = 13.17 +/- 0.46 mu M), 18 (IC50 = 13.15 +/- 0.02 mu M), and 24 (IC50 = 15.65 +/- 0.41 mu M) exhibited good activities. Compounds 1, 3, 4, 5, 9, 12, 15, 18, and 19 were found to be moderately active. Compounds 13, 14, 16, 17, 20-25 showed weak activities with IC50 values ranging between 57 and 88 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.051

文献信息

• Antioxidant properties of phenolic Schiff bases: structure–activity relationship and mechanism of action
  作者：El Hassane Anouar、Salwa Raweh、Imene Bayach、Muhammad Taha、Mohd Syukri Baharudin、Florent Di Meo、Mizaton Hazizul Hasan、Aishah Adam、Nor Hadiani Ismail、Jean-Frédéric F. Weber、Patrick Trouillas

  DOI：10.1007/s10822-013-9692-0

  日期：2013.11

  Phenolic Schiff bases are known for their diverse biological activities and ability to scavenge free radicals. To elucidate (1) the structure-antioxidant activity relationship of a series of thirty synthetic derivatives of 2-methoxybezohydrazide phenolic Schiff bases and (2) to determine the major mechanism involved in free radical scavenging, we used density functional theory calculations (B3P86/6-31+(d

  酚类席夫碱以其多样的生物活性和清除自由基的能力而闻名。为了阐明 (1) 2-甲氧基苯甲酰肼酚类席夫碱的 30 种合成衍生物的结构-抗氧化活性关系和 (2) 确定参与自由基清除的主要机制，我们使用密度泛函理论计算 (B3P86/6 -31+(d,p)) 在可极化连续介质模型中。结果表明，与第一次和第二次 (BDEd) 氢原子转移（内在参数）相关的键解离焓 (BDE) 对合理化抗氧化活性的重要性。除了 OH 基团的数量外，溴取代基的存在在调节抗氧化活性方面也起着重要的作用。