1,1-dimethylethyl 4-{[6-chloro-3-({[(2,3-dichlorophenyl)amino]carbonyl}amino)-2-hydroxyphenyl]sulfonyl}-1-piperazinecarboxylate | 276700-91-5

• 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: 1,1-dimethylethyl 4-{[6-chloro-3-({[(2,3-dichlorophenyl)amino]carbonyl}amino)-2-hydroxyphenyl]sulfonyl}-1-piperazinecarboxylate
• 英文别名: N-[3-[[4-(tert-butoxycarbonyl)piperazin-1-yl] sulfonyl]-4-chloro-2-hydroxyphenyl]-N'-(2,3-dichlorophenyl) urea；N-[3-[4-(tert-butoxycarbonyl)piperazin-1-yl]sulfonyl-4-chloro-2-hydroxyphenyl]-N'-(2,3-dichlorophenyl) urea；tert-butyl 4-[6-chloro-3-[(2,3-dichlorophenyl)carbamoylamino]-2-hydroxyphenyl]sulfonylpiperazine-1-carboxylate
• CAS: 276700-91-5
• 化学式: C₂₂H₂₅Cl₃N₄O₆S
• 分子量: 579.889
• InChiKey: KELRDEGJZFWPKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl 4-{[6-chloro-3-({[(2,3-dichlorophenyl)amino]carbonyl}amino)-2-hydroxyphenyl]sulfonyl}-1-piperazinecarboxylate 在 三氟乙酸 作用下， 反应 4.0h， 生成 N-[4-chloro-2-hydroxy-3-(1-piperazinylsulfonyl)phenyl]-N'-(2,3-dichlorophenyl)urea
  参考文献：
  名称：

  Discovery of CNS Penetrant CXCR2 Antagonists for the Potential Treatment of CNS Demyelinating Disorders

  摘要：

  Structure-activity relationship exploration of the historical biarylurea series led to the identification of novel CNS penetrant CXCR2 antagonists with nanomolar potency, favorable PK profile, and good developability potentials. More importantly, the key compound 22 showed efficacy in a cuprizone-induced demyelination model with twice daily oral administration, thereby supporting CXCR2 to be a potential therapeutic target for the treatment of demyelinating diseases such as multiple sclerosis.

  DOI：

  10.1021/acsmedchemlett.5b00489
• 作为产物：
  描述：

  2-叔丁基-6-氯苯并噁唑-7-磺酰氯 在 硫酸 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 1,1-dimethylethyl 4-{[6-chloro-3-({[(2,3-dichlorophenyl)amino]carbonyl}amino)-2-hydroxyphenyl]sulfonyl}-1-piperazinecarboxylate
  参考文献：
  名称：

  Discovery of CNS Penetrant CXCR2 Antagonists for the Potential Treatment of CNS Demyelinating Disorders

  摘要：

  Structure-activity relationship exploration of the historical biarylurea series led to the identification of novel CNS penetrant CXCR2 antagonists with nanomolar potency, favorable PK profile, and good developability potentials. More importantly, the key compound 22 showed efficacy in a cuprizone-induced demyelination model with twice daily oral administration, thereby supporting CXCR2 to be a potential therapeutic target for the treatment of demyelinating diseases such as multiple sclerosis.

  DOI：

  10.1021/acsmedchemlett.5b00489

文献信息

• Hydroxy diphenyl urea sulfonamides as IL-8 receptor antagonists
  申请人：SmithKline Beecham Corporation

  公开号：US06500863B1

  公开（公告）日：2002-12-31

  Novell IL-8 compounds and methods of using them are provided.

  提供了Novell IL-8化合物及其使用方法。
• [EN] HYDROXY DIPHENYL UREA SULFONAMIDES AS IL-8 RECEPTOR ANTAGONISTS<br/>[FR] SULFONAMIDES HYDROXYDIPHENYLUREE ANTAGONISTES DU RECEPTEUR D'IL-8
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2000035442A1

  公开（公告）日：2000-06-22

  The invention relates to novel hydroxy diphenylurea sulfonamides, compositions and intermediates thereof. The hydroxy diphenylurea sulfonamides are useful in the treatment of disease states mediated by the chemokine, Interleukin-8.

  该发明涉及新型羟基二苯基脲磺酰胺、其组合物和中间体。该羟基二苯基脲磺酰胺在治疗由趋化因子Interleukin-8介导的疾病状态中具有用途。
• Il-8 Receptor Antagonists
  申请人：Busch-Petersen Jakob

  公开号：US20070249625A1

  公开（公告）日：2007-10-25

  This invention relates to novel compounds of Formula (I) to (VII), and compositions thereof, useful in the treatment of disease states mediated by the chemokine, Interleukin-8 (IL-8).

  本发明涉及式（I）至（VII）的新化合物及其组合物，在介导趋化因子白细胞介素-8（IL-8）的疾病状态治疗中有用。
• EP1161232A4
  申请人：——

  公开号：EP1161232A4

  公开（公告）日：2002-09-18
• HYDROXY DIPHENYL UREA SULFONAMIDES AS IL-8 RECEPTOR ANTAGONISTS
  申请人：SmithKline Beecham Corporation

  公开号：EP1161232A1

  公开（公告）日：2001-12-12