6-amino-3-chloro-2-[(4-ethyl-1-piperazinyl)sulfonyl]phenol | 934275-42-0

• 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: 6-amino-3-chloro-2-[(4-ethyl-1-piperazinyl)sulfonyl]phenol
• CAS: 934275-42-0
• 化学式: C₁₂H₁₈ClN₃O₃S
• 分子量: 319.812
• InChiKey: PPUOAKPDDXSVLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  86.87
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-amino-3-chloro-2-[(4-ethyl-1-piperazinyl)sulfonyl]phenol 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-[4-Chloro-3-(4-ethyl-piperazine-1-sulfonyl)-2-hydroxy-phenylamino]-4-(2-propyl-phenylamino)-cyclobut-3-ene-1,2-dione trifluoro-acetic acid salt
  参考文献：
  名称：

  Comparison of N,N′-diarylsquaramides and N,N′-diarylureas as antagonists of the CXCR2 chemokine receptor

  摘要：

  N,N'-diarylsquaramides were prepared and evaluated as antagonists of CXCR2. The compounds were found to be potent and selective antagonists of CXCR2. Significant differences in SAR was observed relative to the previously described N,N'-diarylurea series. As was the case in the N,N'-diarylurea series, placing sulfonamide substituent adjacent to the acidic phenol significantly reduced the clearance in rat pharmacokinetic studies. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.067
• 作为产物：
  描述：

  2,6-二氯苯磺酰氯 在 platinum on activated charcoal 氢氧化钾 、 lithium hydroxide 、 硫酸 、 水 、 氢气 、 硝酸 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 6-amino-3-chloro-2-[(4-ethyl-1-piperazinyl)sulfonyl]phenol
  参考文献：
  名称：

  Comparison of N,N′-diarylsquaramides and N,N′-diarylureas as antagonists of the CXCR2 chemokine receptor

  摘要：

  N,N'-diarylsquaramides were prepared and evaluated as antagonists of CXCR2. The compounds were found to be potent and selective antagonists of CXCR2. Significant differences in SAR was observed relative to the previously described N,N'-diarylurea series. As was the case in the N,N'-diarylurea series, placing sulfonamide substituent adjacent to the acidic phenol significantly reduced the clearance in rat pharmacokinetic studies. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.067

文献信息

• 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.