N-[4-chloro-2-hydroxy-3-(1-piperazinylsulfonyl)phenyl]-N'-(2,3-dichlorophenyl)urea | 276700-92-6

• 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-[4-chloro-2-hydroxy-3-(1-piperazinylsulfonyl)phenyl]-N'-(2,3-dichlorophenyl)urea
• 英文别名: 1-(4-Chloro-2-hydroxy-3-piperazin-1-ylsulfonylphenyl)-3-(2,3-dichlorophenyl)urea
• CAS: 276700-92-6
• 化学式: C₁₇H₁₇Cl₃N₄O₄S
• 分子量: 479.771
• InChiKey: MACGYSKOHXSPKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 N-[4-chloro-2-hydroxy-3-(1-piperazinylsulfonyl)phenyl]-N'-(2,3-dichlorophenyl)urea 在 溶剂黄146 、 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 N-{4-chloro-2-hydroxy-3-[(4-methyl-1-piperazinyl)sulfonyl]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：

  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

文献信息

• HYDROXY DIPHENYL UREA SULFONAMIDES AS IL-8 RECEPTOR ANTAGONISTS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1161232B1

  公开（公告）日：2004-03-24
• Discovery of CNS Penetrant CXCR2 Antagonists for the Potential Treatment of CNS Demyelinating Disorders
  作者：Heng Xu、Hongfu Lu、Zhongmiao Xu、Linbo Luan、Chengyong Li、Yan Xu、Kelly Dong、Jinqiang Zhang、Xiong Li、Yvonne Li、Gentao Liu、Sophie Gong、Yong-Gang Zhao、Ailian Liu、Yueting Zhang、Wei Zhang、Xin Cai、Jia-Ning Xiang、John D. Elliott、Xichen Lin

  DOI：10.1021/acsmedchemlett.5b00489

  日期：2016.4.14

  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.