2-methyl-N-(3-methylpyridin-2-yl)benzamide

• 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-methyl-N-(3-methylpyridin-2-yl)benzamide
• 英文别名: 2-methyl-N-(3-methyl-2-pyridinyl)benzamide
• 化学式: C₁₄H₁₄N₂O
• 分子量: 226.278
• InChiKey: ALBQCKCKXPWSHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-N-(3-methylpyridin-2-yl)benzamide 在 palladium dichloride 作用下， 以 乙腈 为溶剂， 以67 %的产率得到
  参考文献：
  名称：

  Antioxidant and Antiangiogenic Effect of Homoleptic Palladium (II) Carboxamide Complex Loaded Chitosan Modified PLGA Nanoparticles: In vitro Evaluation and In vivo Chick Embryo Chorioallantoic Membrane (CAM) Assay

  摘要：

  背景： 血管生成是一种自然而复杂的机制，由人体形成的生物大分子调控。药用无机化学中的金属基化合物越来越受欢迎，这为开发具有良好抗血管生成效果的新型抗癌药物提供了重要的机会和可能性。 研究目的 本研究旨在探讨使用活性药物纳米粒子制剂进行治疗所取得的成功结果。 方法：采用纳米沉淀/溶剂置换的方法，并对其进行了一些改动： 采用纳米沉淀/溶剂置换法（略有改动）制备基于聚乳酸（PLGA）的 NPs。 结果： 空白制剂的粒径为 82.4-473.9 nm，而添加 API 的 NPs 的粒径为 193.2-678.0 nm。与维生素 C 相比，NP-950-P、NP-390-P 和 NP-350-CSP2 具有显著的抗氧化潜力，其 IC50 值分别为 3.025、5.198 和 7.4242 µg.mL-1。根据显微镜评估，NP-950-P（包括 Pd(PyCrbx)2Cl2，浓度为 50 µg.mL-1 ）和 NP-950-CSP2（包括 Pd(PyCrbx)2Cl2，浓度为 50 µg.mL-1）显示出较强的抗血管生成作用，而与阳性对照（±）-他利度胺 50 µg.mL-1 的浓度相比，其他 NP 制剂显示出较弱的抗血管生成作用。 结论 研究结果表明，制备出的纳米级药物载体系统具有较高的抗氧化活性和抗血管生成活性，尤其是在用 950 制备的纳米颗粒中。据我们所知，这是该领域的首次研究，将为癌症治疗带来新的视角。

  DOI：

  10.2174/1570180820666230214091500
• 作为产物：
  描述：

  对甲苯甲酸 、 2-氨基-3-甲基吡啶 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以42%的产率得到2-methyl-N-(3-methylpyridin-2-yl)benzamide
  参考文献：
  名称：

  Pyridyl Benzamides as a Novel Class of Potent Inhibitors for the Kinetoplastid Trypanosoma brucei

  摘要：

  A whole-organism screen of approximately 87000 compounds against Trypanosoma brucei brucei identified a number of promising compounds for medicinal chemistry optimization. One of these classes of compounds we termed the pyridyl benzamides. While the initial hit had an IC50 of 12 μM, it was small enough to be attractive for further optimization, and we utilized three parallel approaches to develop the structure-activity relationships. We determined that the physicochemical properties for this class are generally favorable with particular positions identified that appear to block metabolism when substituted and others that modulate solubility. Our most active compound is 79, which has an IC50 of 0.045 μM against the human pathogenic strain Trypanosoma brucei rhodesiense and is more than 4000 times less active against the mammalian L6 cell line.

  DOI：

  10.1021/jm500191u

文献信息

• Pyridyl Benzamides as a Novel Class of Potent Inhibitors for the Kinetoplastid <i>Trypanosoma brucei</i>
  作者：Lori Ferrins、Michelle Gazdik、Raphaël Rahmani、Swapna Varghese、Melissa L. Sykes、Amy J. Jones、Vicky M. Avery、Karen L. White、Eileen Ryan、Susan A. Charman、Marcel Kaiser、Christel A. S. Bergström、Jonathan B. Baell

  DOI：10.1021/jm500191u

  日期：2014.8.14

  A whole-organism screen of approximately 87000 compounds against Trypanosoma brucei brucei identified a number of promising compounds for medicinal chemistry optimization. One of these classes of compounds we termed the pyridyl benzamides. While the initial hit had an IC50 of 12 μM, it was small enough to be attractive for further optimization, and we utilized three parallel approaches to develop the structure-activity relationships. We determined that the physicochemical properties for this class are generally favorable with particular positions identified that appear to block metabolism when substituted and others that modulate solubility. Our most active compound is 79, which has an IC50 of 0.045 μM against the human pathogenic strain Trypanosoma brucei rhodesiense and is more than 4000 times less active against the mammalian L6 cell line.
• Antioxidant and Antiangiogenic Effect of Homoleptic Palladium (II) Carboxamide Complex Loaded Chitosan Modified PLGA Nanoparticles: In vitro Evaluation and In vivo Chick Embryo Chorioallantoic Membrane (CAM) Assay
  作者：A. Alper Öztürk、Hakan Ünver、H. Tuba Kıyan

  DOI：10.2174/1570180820666230214091500

  日期：2023.8

  Angiogenesis is a natural and complex mechanism that is regulated by biomolecules formed by the body. Medicinal inorganic chemistry is increasing in popularity due to metal-based compounds, offering significant chances and possibilities for building novel anti-cancer medicines with promising anti-angiogenic effects.

  This study aimed to examine the successful results obtained from treatments with nanoparticle formulations of active drug substances.

  The nanoprecipitation/solvent displacement approach, with some changes, was used to make PLGA-based NPs.

  The particle size obtained in the blank formulation was 82.4–473.9 nm, while the particle size in the API-loaded NPs was 193.2–678.0 nm. Among the formulations, NP-950-P, NP-390-P, and NP-350-CSP2 were found to have significant antioxidant potentials with IC50 values of 3.025, 5.198, and 7.4242 µg.mL-1, respectively, when compared to Vit C. According to the microscopic evaluations, NP-950-P (including Pd(PyCrbx)2Cl2 as 50 µg.pellet-1) and NP-950-CSP2 (including Pd(PyCrbx)2Cl2 as 50 µg.pellet-1) showed strong anti-angiogenic effect whereas the other NP formulations showed weak anti-angiogenic effect when compared with the positive control (±)-Thalidomide at the concentration of 50 µg.pellet-1.

  When the results were examined, it was found that nanoscale drug carrier systems were prepared, and high antioxidant activity and anti-angiogenesis activity were detected, especially in nanoparticles prepared with 950. As per our knowledge, it is the first study in this field that will bring a new perspective to cancer treatment.

  背景： 血管生成是一种自然而复杂的机制，由人体形成的生物大分子调控。药用无机化学中的金属基化合物越来越受欢迎，这为开发具有良好抗血管生成效果的新型抗癌药物提供了重要的机会和可能性。 研究目的 本研究旨在探讨使用活性药物纳米粒子制剂进行治疗所取得的成功结果。 方法：采用纳米沉淀/溶剂置换的方法，并对其进行了一些改动： 采用纳米沉淀/溶剂置换法（略有改动）制备基于聚乳酸（PLGA）的 NPs。 结果： 空白制剂的粒径为 82.4-473.9 nm，而添加 API 的 NPs 的粒径为 193.2-678.0 nm。与维生素 C 相比，NP-950-P、NP-390-P 和 NP-350-CSP2 具有显著的抗氧化潜力，其 IC50 值分别为 3.025、5.198 和 7.4242 µg.mL-1。根据显微镜评估，NP-950-P（包括 Pd(PyCrbx)2Cl2，浓度为 50 µg.mL-1 ）和 NP-950-CSP2（包括 Pd(PyCrbx)2Cl2，浓度为 50 µg.mL-1）显示出较强的抗血管生成作用，而与阳性对照（±）-他利度胺 50 µg.mL-1 的浓度相比，其他 NP 制剂显示出较弱的抗血管生成作用。 结论 研究结果表明，制备出的纳米级药物载体系统具有较高的抗氧化活性和抗血管生成活性，尤其是在用 950 制备的纳米颗粒中。据我们所知，这是该领域的首次研究，将为癌症治疗带来新的视角。