(2-fluoro-5-methoxypyridin-3-yl)boronic acid | 1253577-76-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-fluoro-5-methoxypyridin-3-yl)boronic acid
• 英文别名: 2-Fluoro-5-methoxypyridine-3-boronic acid
• CAS: 1253577-76-2
• 化学式: C₆H₇BFNO₃
• 分子量: 170.936
• InChiKey: GUGFLRVPERPDJR-UHFFFAOYSA-N

物化性质

• 沸点：
  384.2±52.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.09
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  62.6
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  (2-fluoro-5-methoxypyridin-3-yl)boronic acid 在 二氯双[二叔丁基-(4-二甲基氨基苯基)膦]钯(II) 、 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 生成 N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-methoxypyridin-2-ylamino)-2-chloropyridin-3-yl)morpholine-4-sulfonamide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of dual PI3K/mTOR inhibitors based on a 4-amino-6-methyl-1,3,5-triazine sulfonamide scaffold

  摘要：

  Phosphoinositide 3-kinase (PI3K) is an important target in oncology due to the deregulation of the PI3K/Akt signaling pathway in a wide variety of tumors. A series of 4-amino-6-methyl-1,3,5-triazine sulfonamides were synthesized and evaluated as inhibitors of PI3K. The synthesis, in vitro biological activities, pharmacokinetic and in vivo pharmacodynamic profiling of these compounds are described. The most promising compound from this investigation (compound 3j) was found to be a pan class I PI3K inhibitor with a moderate (>10-fold) selectivity over the mammalian target of rapamycin (mTOR) in the enzyme assay. In a U87 MG cellular assay measuring phosphorylation of Akt, compound 3j displayed low double digit nanomolar IC50 and exhibited good oral bioavailability in rats (F-oral = 63%). Compound 3j also showed a dose dependent reduction in the phosphorylation of Akt in a U87 tumor pharmacodynamic model with a plasma EC50 = 193 nM (91 ng/mL). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.078
• 作为产物：
  描述：

  二异丙胺 、 正丁基锂 、 2-氟-5-甲氧基吡啶 、 硼酸三异丙酯 在 sodium hydroxide 、 盐酸 、 乙酸乙酯 、 Sodium sulfate-III 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 以to afford 0.593 g of tan color solid的产率得到(2-fluoro-5-methoxypyridin-3-yl)boronic acid
  参考文献：
  名称：

  Inhibitors of PI3 kinase and/or mTOR

  摘要：

  本发明涉及式I化合物或其药学上可接受的盐；使用该化合物治疗疾病或病症的方法，例如癌症；以及含有该化合物的药物组合物，其中变量如本文所定义。

  公开号：

  US08362241B2

文献信息

• Synthesis and Antiproliferative Evaluation of Novel 5-Substituted Pyridazin-4-Amine Derivatives
  作者：Bin Liu、Xiaona Xu、Hongjuan Tong、Zhoujing Zhu、Wenqiang Tang、Chu Tang

  DOI：10.1080/00304948.2022.2041956

  日期：2022.7.4

  Published in Organic Preparations and Procedures International: The New Journal for Organic Synthesis (Vol. 54, No. 4, 2022)

  （2022 年）。新型 5-取代哒嗪-4-胺衍生物的合成和抗增殖评价。国际有机制剂和程序。领先于印刷。
• INHIBITORS OF PI3 KINASE AND/OR MTOR
  申请人：Andrews Kristin

  公开号：US20100273764A1

  公开（公告）日：2010-10-28

  The present invention relates to compounds of Formula I, or a pharmaceutically acceptable salt thereof; methods of treating diseases or conditions, such as cancer, using the compounds; and pharmaceutical compositions containing the compounds, wherein the variables are as defined herein.

  本发明涉及公式I的化合物或其药学上可接受的盐；使用该化合物治疗疾病或病症的方法，如癌症；以及含有该化合物的制药组合物，其中变量在此定义。
• Inhibitors of PI3 Kinase and/or mTOR
  申请人：Amgen Inc.

  公开号：US20130079303A1

  公开（公告）日：2013-03-28

  The present invention relates to compounds of Formula I, or a pharmaceutically acceptable salt thereof; methods of treating diseases or conditions, such as cancer, using the compounds; and pharmaceutical compositions containing the compounds, wherein the variables are as defined herein.

  本发明涉及公式I的化合物，或其药学可接受的盐；使用这些化合物治疗疾病或病况的方法，如癌症；以及含有这些化合物的药物组合物，其中变量的定义如本文所述。
• 一种5-取代哒嗪-4-胺衍生物、制备方法和用途
  申请人：陕西国际商贸学院

  公开号：CN114042069A

  公开（公告）日：2022-02-15

  本发明属于化合物合成及应用技术领域，具体涉及一种5‑取代哒嗪‑4‑胺衍生物在制备抗肿瘤药物中的用途，5‑取代哒嗪‑4‑胺衍生物，其结构式如式(Ⅰ)所示：其中，R是烯基或芳基；烯基为烯丙基或环戊烯基；芳基为苯基、取代苯基、取代吡啶基、萘基、吲哚基或喹啉基。本发明提供的5‑取代哒嗪‑4‑胺衍生物对肿瘤细胞具有优异的抑制活性，能作为抗肿瘤性疾病的药物广泛应用，且该衍生物毒性低，制备方法简单，条件温和；为哒嗪类抗肿瘤药物的开发应用提供一种新的思路。
• Synthesis and structure–activity relationships of dual PI3K/mTOR inhibitors based on a 4-amino-6-methyl-1,3,5-triazine sulfonamide scaffold
  作者：Ryan P. Wurz、Longbin Liu、Kevin Yang、Nobuko Nishimura、Yunxin Bo、Liping H. Pettus、Sean Caenepeel、Daniel J. Freeman、John D. McCarter、Erin L. Mullady、Tisha San Miguel、Ling Wang、Nancy Zhang、Kristin L. Andrews、Douglas A. Whittington、Jian Jiang、Raju Subramanian、Paul E. Hughes、Mark H. Norman

  DOI：10.1016/j.bmcl.2012.06.078

  日期：2012.9

  Phosphoinositide 3-kinase (PI3K) is an important target in oncology due to the deregulation of the PI3K/Akt signaling pathway in a wide variety of tumors. A series of 4-amino-6-methyl-1,3,5-triazine sulfonamides were synthesized and evaluated as inhibitors of PI3K. The synthesis, in vitro biological activities, pharmacokinetic and in vivo pharmacodynamic profiling of these compounds are described. The most promising compound from this investigation (compound 3j) was found to be a pan class I PI3K inhibitor with a moderate (>10-fold) selectivity over the mammalian target of rapamycin (mTOR) in the enzyme assay. In a U87 MG cellular assay measuring phosphorylation of Akt, compound 3j displayed low double digit nanomolar IC50 and exhibited good oral bioavailability in rats (F-oral = 63%). Compound 3j also showed a dose dependent reduction in the phosphorylation of Akt in a U87 tumor pharmacodynamic model with a plasma EC50 = 193 nM (91 ng/mL). (C) 2012 Elsevier Ltd. All rights reserved.