3-Bromo-5-chlorobenzene-1-sulfonamide | 1261524-60-0

• 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: 3-Bromo-5-chlorobenzene-1-sulfonamide
• 英文别名: 3-bromo-5-chlorobenzenesulfonamide
• CAS: 1261524-60-0
• 化学式: C₆H₅BrClNO₂S
• 分子量: 270.534
• InChiKey: JGIJYZFOWSNYFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 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：
  68.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Bromo-5-chlorobenzene-1-sulfonamide 、 C₁₀H₂₁NO 在 potassium phosphate 、 copper(l) iodide 、 L-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 以51%的产率得到3-chloro-5-[(cis-5-hydroxy-1,3,3-trimethyl-cyclohexylmethyl)-amino]-benzenesulfonamide
  参考文献：
  名称：

  Design and Synthesis of Benzenesulfonamide Derivatives as Potent Anti-Influenza Hemagglutinin Inhibitors

  摘要：

  Structural optimization of salicylamide-based hemagglutinin (HA) inhibitor 1 resulted in the identification of cis-3-(5-hydroxy-1,3,3-timethylcyclohexylmethylamino)benzenesulfonamide 28 and its derivatives as potent anti-influenza agents. The lead compound 28 and its 2-chloro analogue 40 can effectively prevent cytopathic effects (CPE) caused by infection of influenza A/Weiss/43 strain (H1N1) with EC(50) values of 210 and 86 nM, respectively. Mechanism of action studies indicate that 40 and its analogues inhibit the virus fusion with host endosome membrane by binding to HA and stabilizing the prefusion HA structure. With significantly improved metabolic stability, the reported series represents the first generation of orally bioavailable HA inhibitors that have a good selectivity window and potential for further development as novel anti-influenza agents.

  DOI：

  10.1021/ml2000627
• 作为产物：
  描述：

  3-溴-5-氯苯胺 在 盐酸 、 氨 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.17h， 生成 3-Bromo-5-chlorobenzene-1-sulfonamide
  参考文献：
  名称：

  Design and Synthesis of Benzenesulfonamide Derivatives as Potent Anti-Influenza Hemagglutinin Inhibitors

  摘要：

  Structural optimization of salicylamide-based hemagglutinin (HA) inhibitor 1 resulted in the identification of cis-3-(5-hydroxy-1,3,3-timethylcyclohexylmethylamino)benzenesulfonamide 28 and its derivatives as potent anti-influenza agents. The lead compound 28 and its 2-chloro analogue 40 can effectively prevent cytopathic effects (CPE) caused by infection of influenza A/Weiss/43 strain (H1N1) with EC(50) values of 210 and 86 nM, respectively. Mechanism of action studies indicate that 40 and its analogues inhibit the virus fusion with host endosome membrane by binding to HA and stabilizing the prefusion HA structure. With significantly improved metabolic stability, the reported series represents the first generation of orally bioavailable HA inhibitors that have a good selectivity window and potential for further development as novel anti-influenza agents.

  DOI：

  10.1021/ml2000627