6-amino-5-bromonicotinamide | 1171622-87-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-amino-5-bromonicotinamide
• 英文别名: 6-amino-5-bromopyridine-3-carboxamide
• CAS: 1171622-87-9
• 化学式: C₆H₆BrN₃O
• mdl: MFCD14281999
• 分子量: 216.037
• InChiKey: OIQGWDAWZBDVNI-UHFFFAOYSA-N

物化性质

• 沸点：
  338.5±42.0 °C(Predicted)
• 密度：
  1.802±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-amino-5-bromonicotinamide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 cesium fluoride 作用下， 以 三乙胺 、 乙腈 为溶剂， 反应 4.0h， 生成 6-amino-5-((5-((3,5-dimethoxyphenyl)carbamoyl)-2-methylphenyl)ethynyl)nicotinamide
  参考文献：
  名称：

  Novel Class of Colony-Stimulating Factor 1 Receptor Kinase Inhibitors Based on ano-Aminopyridyl Alkynyl Scaffold as Potential Treatment for Inflammatory Disorders

  摘要：

  Colony-stimulating factor 1 receptor (CSF-1R) is involved in inflammatory disorders as well as in many types of cancer. Based on high-throughput screening and docking results, we performed a detailed structure-activity-relationship study, leading to the discovery of a new series of compounds with nanomolar IC50 values against CSF-1R without the inhibition of fibroblast growth factor receptors. One of the most promising hits, compound 29, potently inhibited CSF-1R kinase with an IC50 value of 0.7 nM, while it showed no inhibition to the same family member FMS-like tyrosine kinase 3. Compound 29 displayed excellent anti-inflammatory effects against RAW264.7 macrophages indicated by significant inhibition against the activation of the CSF-1R pathway with low cytotoxicity. In addition, compound 29 exhibited strong in vivo anti-inflammatory efficacy alongside favorable drug characteristics. This novel compound 29 may serve as a new drug candidate with promising applications in inflammatory disorders.

  DOI：

  10.1021/acs.jmedchem.9b01912
• 作为产物：
  描述：

  6-氨基烟酰胺 在 sodium hydroxide 、 溴 作用下， 以 溶剂黄146 为溶剂， 生成 6-amino-5-bromonicotinamide
  参考文献：
  名称：

  Pyridine derivatives useful as cyclooxygenase inhibitor

  摘要：

  一种化合物的分子式（I），其中R1为氢、卤素、羰基、氰基、甲酰基或选择性取代有卤素、氨基或保护氨基的低烷基，R2为氢、卤素、氰基或低烷氧基，R3为苯基或吡啶基，每个基团都被低烷氧基取代，R4为低烷氧基；条件是R1或R2中的一个是氢，则另一个不是氢，或其盐，可用作药物。

  公开号：

  US20030119877A1

文献信息

• PYRIDINE DERIVATIVES USEFUL AS CYCLOOXYGENASE INHIBITOR
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP1355885A1

  公开（公告）日：2003-10-29
• [EN] PYRIDINE DERIVATIVES USEFUL AS CYCLOOXYGENASE INHIBITOR<br/>[FR] DERIVES DE PYRIDINE UTILES EN TANT QU'INHIBITEURS DE CYCLO-OXYGENASE
  申请人：FUJISAWA PHARMACEUTICAL CO

  公开号：WO2002055502A1

  公开（公告）日：2002-07-18

  A compound of the formula (I), wherein R1 is hydrogen, halogen, carbymoyl, cyano, formuly, or lower alkyl optionally substituted with halogen, amino or a protected amino; R2 is hydrogen, halogen, cyano or lower alkoxy; R3 is phenyl or pyridyl, each of which is substituted with lower alkoxy; and R4 is lower alkoxy; provided that either R1 or R2 is hydrogen, then the other is other than hydrogen, or its salts, which are useful as a medicament.
• Novel Class of Colony-Stimulating Factor 1 Receptor Kinase Inhibitors Based on an<i>o</i>-Aminopyridyl Alkynyl Scaffold as Potential Treatment for Inflammatory Disorders
  作者：Zhicheng Xie、Bing Wu、Yingqiang Liu、Wenming Ren、Linjiang Tong、Caigui Xiang、Aihuan Wei、Yuanzhuo Gao、Limin Zeng、Hua Xie、Wei Tang、Youhong Hu

  DOI：10.1021/acs.jmedchem.9b01912

  日期：2020.2.13

  Colony-stimulating factor 1 receptor (CSF-1R) is involved in inflammatory disorders as well as in many types of cancer. Based on high-throughput screening and docking results, we performed a detailed structure-activity-relationship study, leading to the discovery of a new series of compounds with nanomolar IC50 values against CSF-1R without the inhibition of fibroblast growth factor receptors. One of the most promising hits, compound 29, potently inhibited CSF-1R kinase with an IC50 value of 0.7 nM, while it showed no inhibition to the same family member FMS-like tyrosine kinase 3. Compound 29 displayed excellent anti-inflammatory effects against RAW264.7 macrophages indicated by significant inhibition against the activation of the CSF-1R pathway with low cytotoxicity. In addition, compound 29 exhibited strong in vivo anti-inflammatory efficacy alongside favorable drug characteristics. This novel compound 29 may serve as a new drug candidate with promising applications in inflammatory disorders.
• Pyridine derivatives useful as cyclooxygenase inhibitor
  申请人：——

  公开号：US20030119877A1

  公开（公告）日：2003-06-26

  A compound of the formula (I), wherein R 1 is hydrogen, halogen, carbymoyl, cyano, formuly, or lower alkyl optionally substituted with halogen, amino or a protected amino, R 2 is hydrogen, halogen, cyano or lower alkoxy, R 3 is phenyl or pyridyl, each of which is substituted with lower alkoxy, and R 4 is lower alkoxy; provided that either R 1 or R 2 is hydrogen, then the other is other than hydrogen, or its salts, which are useful as a medicament.

  一种化合物的分子式（I），其中R1为氢、卤素、羰基、氰基、甲酰基或选择性取代有卤素、氨基或保护氨基的低烷基，R2为氢、卤素、氰基或低烷氧基，R3为苯基或吡啶基，每个基团都被低烷氧基取代，R4为低烷氧基；条件是R1或R2中的一个是氢，则另一个不是氢，或其盐，可用作药物。