4-fluoro-N-(5-hydroxy-3,4,6-trimethylpyridin-2-yl)benzamide | 1616249-77-4

• 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-fluoro-N-(5-hydroxy-3,4,6-trimethylpyridin-2-yl)benzamide
• 英文别名: N-(5-hydroxy-3,4,6-trimethylpyridine-2-yl)-4-fluorobenzamide；N-(5-hydroxy-3,4,6-trimethylpyridin-2-yl)-4-fluorobenzamide
• CAS: 1616249-77-4
• 化学式: C₁₅H₁₅FN₂O₂
• 分子量: 274.295
• InChiKey: GGVJFSBLLUICFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-(benzyloxy)-3,4,6-trimethylpyridin-2-amine 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 4-fluoro-N-(5-hydroxy-3,4,6-trimethylpyridin-2-yl)benzamide
  参考文献：
  名称：

  AMIDOPYRIDINOL DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING SAME AS ACTIVE COMPONENT

  摘要：

  本发明涉及一种酰胺吡啶醇衍生物或其药学上可接受的盐，以及包括酰胺吡啶醇衍生物或其药学上可接受的盐作为活性成分的药物组合物。由化学式1表示的酰胺吡啶醇衍生物或其药学上可接受的盐在绒毛膜模型中具有出色的抗血管生成作用，因此可用作预防或治疗与血管生成相关的疾病，如黄斑变性或关节炎的药物，并且在炎性肠道疾病模型中具有出色的结肠炎抑制作用，因此可用作预防或治疗炎性肠道疾病的药物。在绒毛膜模型中接种肺癌细胞时，化学式1的酰胺吡啶醇衍生物或其药学上可接受的盐抑制了由肿瘤发生引起的血管生成和肿瘤生长，并且还抑制了在癌症转移和侵袭中发挥重要作用的半胱氨酸蛋白酶S的活性，因此可用作抑制癌症生长和转移的药物。

  公开号：

  US20160068489A1

文献信息

• Synthesis and antiangiogenic activity of 6-amido-2,4,5-trimethylpyridin-3-ols
  作者：Hyunji Lee、Suhrid Banskota、Dong-Guk Kim、Jae-Hui Been、You-Jin Jin、Jaya Gautam、Hyeonjin Jang、Tae-gyu Nam、Jung-Ae Kim、Byeong-Seon Jeong

  DOI：10.1016/j.bmcl.2014.05.005

  日期：2014.7

  We recently reported that 6-aminoalkyl-2,4,5-trimethylpyridin-3-ols, novel series of 6-aminopyridin-3-ol-based antioxidants, have high antiangiogenic activities. In pursuit of wider variety in the analogues, we here report the synthesis and antiangiogenic activities of 6-amidoalkyl-2,4,5-trimethylpyridin-3-ols, which would not be considered excellent antioxidants because of the poorer electron-donating effect of the C(6)-amido group than the corresponding C(6)-amino group. The selected 6-amido compounds showed up to several fold-higher antiangiogenic activities and up to an order of magnitude better antitumor activities in the chick embryo chorioallantoic membrane (CAM) assay than SU4312, a positive control. We also found that paracetamol, as a direct phenolic analogue of our simplest 6-amidopyridin-3-ol, showed a moderate level of antiangiogenic activity. We propose this study will offer a basis for a scaffold of novel angiogenesis inhibitors that can perturb angiogenesis-related pathologies. (C) 2014 Elsevier Ltd. All rights reserved.
• KR101612179
  申请人：——

  公开号：——

  公开（公告）日：——
• US9802897B2
  申请人：——

  公开号：US9802897B2

  公开（公告）日：2017-10-31
• [EN] AMIDOPYRIDINOL DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING SAME AS ACTIVE COMPONENT<br/>[FR] DÉRIVÉ D'AMIDOPYRIDINOL OU SEL PHARMACEUTIQUEMENT ACCEPTABLE CORRESPONDANT ET COMPOSITION PHARMACEUTIQUE LE COMPRENANT COMME CONSTITUANT ACTIF
  申请人：UNIV YEUNGNAM RES COOPERATION FOUNDATION

  公开号：WO2014171801A1

  公开（公告）日：2014-10-23

  본 발명은 아미도피리딘올 유도체 또는 이의 약제학적 허용가능한 염, 및 이를 유효성분으로 함유하는 약학조성물에 관한 것으로, 화학식 1로 표시되는 아미도피리딘올 유도체 또는 이의 약제학적 허용가능한 염은 융모요막 모델에서의 신생혈관형성 억제 효과가 탁월하여, 황반변성 또는 관절염 등과 같은 혈관신생으로 인한 질환의 예방 또는 치료용 약제로서 유용하게 사용될 수 있으며, 염증성 장질환 모델에서의 대장염 억제 효과가 탁월하여, 염증성 장질환의 예방 또는 치료용 약제로서 유용하게 사용될 수 있을 뿐 아니라, 융모요막 모델에 폐암세포를 접종한 후, 종양 형성에 의한 혈관신생 및 종양 성장을 억제할 뿐 아니라, 암 전이 및 침윤에 중요한 역할을 수행하는 카텝신 S의 활성을 억제하므로, 암 성장 억제 및 암 전이 억제용 약제로서 유용하게 사용될 수 있다.
• AMIDOPYRIDINOL DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING SAME AS ACTIVE COMPONENT
  申请人：Research Cooperation Foundation of Yeungnam University

  公开号：US20160068489A1

  公开（公告）日：2016-03-10

  The present invention relates to an amidopyridinol derivative or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition including an amidopyridinol derivative or a pharmaceutically acceptable salt thereof as an active component. An amidopyridinol derivative represented by Chemical Formula 1 or a pharmaceutically acceptable salt thereof has an excellent antiangiogenic effect in a chorioallantoic membrane model, and thus is useful as an agent for preventing or treating diseases associated with angiogenesis, such as macular degeneration or arthritis, and also has an excellent colitis-inhibitory effect in a model of inflammatory bowel diseases, and thus is useful as an agent for preventing or treating inflammatory bowel diseases. Upon inoculation of lung cancer cells in a chorioallantoic membrane model, the amidopyridinol derivative of Chemical Formula 1 or the pharmaceutically acceptable salt thereof inhibits angiogenesis and tumor growth that are caused by tumorigenesis, and also inhibits the activity of cathepsin S that plays an important role in metastasis and invasion of cancer, and thus is useful as an inhibitor of cancer growth and metastasis.

  本发明涉及一种酰胺吡啶醇衍生物或其药学上可接受的盐，以及包括酰胺吡啶醇衍生物或其药学上可接受的盐作为活性成分的药物组合物。由化学式1表示的酰胺吡啶醇衍生物或其药学上可接受的盐在绒毛膜模型中具有出色的抗血管生成作用，因此可用作预防或治疗与血管生成相关的疾病，如黄斑变性或关节炎的药物，并且在炎性肠道疾病模型中具有出色的结肠炎抑制作用，因此可用作预防或治疗炎性肠道疾病的药物。在绒毛膜模型中接种肺癌细胞时，化学式1的酰胺吡啶醇衍生物或其药学上可接受的盐抑制了由肿瘤发生引起的血管生成和肿瘤生长，并且还抑制了在癌症转移和侵袭中发挥重要作用的半胱氨酸蛋白酶S的活性，因此可用作抑制癌症生长和转移的药物。