N-(5-bromo-2-chloropyridin-3-yl)-N-methylbenzenesulfonamide | 1309778-75-3

• 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: N-(5-bromo-2-chloropyridin-3-yl)-N-methylbenzenesulfonamide
• 英文别名: N-(5-Bromo-2-chloro-3-pyridinyl)-N-methylbenzenesulfonamide
• CAS: 1309778-75-3
• 化学式: C₁₂H₁₀BrClN₂O₂S
• 分子量: 361.647
• InChiKey: ANVYUKZVHVETRD-UHFFFAOYSA-N

物化性质

• 沸点：
  469.3±55.0 °C(Predicted)
• 密度：
  1.655±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-氮杂吲哚-5-硼酸频哪醇酯 、 N-(5-bromo-2-chloropyridin-3-yl)-N-methylbenzenesulfonamide 在 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 以43%的产率得到N-(2-chloro-5-(1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-3-yl)-N-methyl benzene sulfonamide
  参考文献：
  名称：

  Development of anti-breast cancer PI3K inhibitors based on 7-azaindole derivatives through scaffold hopping: Design, synthesis and in vitro biological evaluation

  摘要：

  DOI：

  10.1016/j.bioorg.2021.105405
• 作为产物：
  描述：

  2-甲基-3-氨基-5-溴吡啶 在 吡啶 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 18.42h， 生成 N-(5-bromo-2-chloropyridin-3-yl)-N-methylbenzenesulfonamide
  参考文献：
  名称：

  Optimization of Novel Indazoles as Highly Potent and Selective Inhibitors of Phosphoinositide 3-Kinase δ for the Treatment of Respiratory Disease

  摘要：

  Optimization of lead compound 1, through extensive use of structure-based design and a focus on PI3K delta potency, isoform selectivity, and inhaled PK properties, led to the discovery of clinical candidates 2 (GSK2269557) and 3 (G5K2292767) for the treatment of respiratory indications via inhalation. Compounds 2 and 3 are both highly selective for PI3K delta over the closely related isoforms and are active in a disease relevant brown Norway rat acute OVA model of Th2-driven lung inflammation.

  DOI：

  10.1021/acs.jmedchem.5b00767

文献信息

• [EN] INDAZOLE DERIVATIVES AS PI 3 - KINASE INHIBITORS<br/>[FR] DÉRIVÉS D'INDAZOLE COMME INHIBITEURS DES PI3-KINASES
  申请人：GLAXO GROUP LTD

  公开号：WO2011067366A1

  公开（公告）日：2011-06-09

  The invention is directed to certain novel compounds. Specifically, the invention is directed to compounds of formula (I) and salts thereof. The compounds of the invention are inhibitors of PI3-kinase activity.

  这项发明涉及某些新颖化合物。具体而言，该发明涉及具有化学式(I)及其盐的化合物。该发明的化合物是PI3-激酶活性的抑制剂。
• INDAZOLE DERIVATIVES AS PI 3-KINASE
  申请人：Baldwin Ian Robert

  公开号：US20120238571A1

  公开（公告）日：2012-09-20

  The invention is directed to certain novel compounds. Specifically, the invention is directed to compounds of formula (I): and salts thereof. The compounds of the invention are inhibitors of PI3-kinase activity.

  本发明涉及某些新型化合物。具体而言，本发明涉及公式（I）的化合物及其盐。本发明的化合物是PI3-激酶活性抑制剂。
• Design, synthesis and in vitro biological evaluation of 2-aminopyridine derivatives as novel PI3Kδ inhibitors for hematological cancer
  作者：Chengbin Yang、Yimin Gong、Yunjian Gao、Mingli Deng、Xiaofeng Liu、Yongtai Yang、Yun Ling、Yu Jia、Yaming Zhou

  DOI：10.1016/j.bmcl.2023.129152

  日期：2023.2
• Optimization of Novel Indazoles as Highly Potent and Selective Inhibitors of Phosphoinositide 3-Kinase δ for the Treatment of Respiratory Disease
  作者：Kenneth Down、Augustin Amour、Ian R. Baldwin、Anthony W. J. Cooper、Angela M. Deakin、Leigh M. Felton、Stephen B. Guntrip、Charlotte Hardy、Zoë A. Harrison、Katherine L. Jones、Paul Jones、Suzanne E. Keeling、Joelle Le、Stefano Livia、Fiona Lucas、Christopher J. Lunniss、Nigel J. Parr、Ed Robinson、Paul Rowland、Sarah Smith、Daniel A. Thomas、Giovanni Vitulli、Yoshiaki Washio、J. Nicole Hamblin

  DOI：10.1021/acs.jmedchem.5b00767

  日期：2015.9.24

  Optimization of lead compound 1, through extensive use of structure-based design and a focus on PI3K delta potency, isoform selectivity, and inhaled PK properties, led to the discovery of clinical candidates 2 (GSK2269557) and 3 (G5K2292767) for the treatment of respiratory indications via inhalation. Compounds 2 and 3 are both highly selective for PI3K delta over the closely related isoforms and are active in a disease relevant brown Norway rat acute OVA model of Th2-driven lung inflammation.
• Development of anti-breast cancer PI3K inhibitors based on 7-azaindole derivatives through scaffold hopping: Design, synthesis and in vitro biological evaluation
  作者：Chengbin Yang、Mingzhu Lu、Yi Chen、Ruiqing Xiang、Tianze Qiu、Yu Jia、Yongtai Yang、Xiaofeng Liu、Mingli Deng、Yun Ling、Yaming Zhou

  DOI：10.1016/j.bioorg.2021.105405

  日期：2021.12