3-溴-5-氟-1-对甲苯磺酰基-7-氮杂吲哚 | 1417421-99-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-溴-5-氟-1-对甲苯磺酰基-7-氮杂吲哚
• 英文名称: 3-bromo-5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridine
• 英文别名: 3-bromo-5-fluoro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine；3-bromo-5-fluoro-1-(p-toluenesulfonyl)-1H-pyrrolo[2,3-b]pyridine；3-Bromo-5-fluoro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine；3-bromo-5-fluoro-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridine
• CAS: 1417421-99-8
• 化学式: C₁₄H₁₀BrFN₂O₂S
• 分子量: 369.214
• InChiKey: XAAFAPOSALSONG-UHFFFAOYSA-N

物化性质

• 密度：
  1.73g/cm3 at 20℃
• LogP：
  4.2 at pH7

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  60.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-溴-5-氟-1-对甲苯磺酰基-7-氮杂吲哚 在 四(三苯基膦)钯 、 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 potassium acetate 、 sodium carbonate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 26.5h， 生成 tert-butyl N-[(1R,3S)-3-[[5-fluoro-2-[5-fluoro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]amino]cyclohexyl]carbamate
  参考文献：
  名称：

  Discovery of a Novel, First-in-Class, Orally Bioavailable Azaindole Inhibitor (VX-787) of Influenza PB2

  摘要：

  In our effort to develop agents for the treatment of influenza, a phenotypic screening approach utilizing a cell protection assay identified a series of azaindole based inhibitors of the cap-snatching function of the PB2 subunit of the influenza A viral polymerase complex. Using a bDNA viral replication assay (Wagaman, P. C.; Leong, M. A.; Simmen, K. A. Development of a novel influenza A antiviral assay. J. Virol. Methods 2002, 105, 105-114) in cells as a direct measure of antiviral activity, we discovered a set of cyclohexyl carboxylic acid analogues, highlighted by VX-787 (2). Compound 2 shows strong potency versus multiple influenza A strains, including pandemic 2009 H1N1 and avian H5N1 flu strains, and shows an efficacy profile in a mouse influenza model even when treatment was administered 48 h after infection. Compound 2 represents a first-in-class, orally bioavailable, novel compound that offers potential for the treatment of both pandemic and seasonal influenza and has a distinct advantage over the current standard of care treatments including potency, efficacy, and extended treatment window.

  DOI：

  10.1021/jm5007275
• 作为产物：
  描述：

  2-氨基-3-溴-5-氟吡啶 在 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、