6-chloro-2-hydroxy-3-nitrobenzamide | 454471-77-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 6-chloro-2-hydroxy-3-nitrobenzamide
• CAS: 454471-77-3
• 化学式: C₇H₅ClN₂O₄
• 分子量: 216.581
• InChiKey: GVHAUXLBRHUCFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 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：
  109
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-chloro-2-hydroxy-3-nitrobenzamide 在 platinum on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 6-chloro-3-(2-chloro-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-benzamide
  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：

  6-chloro-2-hydroxy-3-nitrobenzonitrile 在 硫酸 作用下， 以89%的产率得到6-chloro-2-hydroxy-3-nitrobenzamide
  参考文献：
  名称：

  Discovery of potent and orally bioavailable N,N′-diarylurea antagonists for the CXCR2 chemokine receptor

  摘要：

  A series of 3-substituted N,N'-diarylureas was prepared and the structure-activity relationship relative to CXCR2 receptor affinity as well as their pharmacokinetic properties were examined. In vitro microsomal metabolism studies indicated that the lower clearance rates of the 3-sulfonamido-substituted compounds were most likely due to the suppression of glucuronidation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.097

文献信息

• Il-8 receptor antagonists
  申请人：——

  公开号：US20040132694A1

  公开（公告）日：2004-07-08

  This invention relates to the novel use of amide squaramides in the treatment of disease states mediated by the chemokine, Interleukin-8 (IL-8).

  本发明涉及酰胺并四氢喹啉酰胺在治疗由趋化因子白细胞介素-8（IL-8）介导的疾病状态中的新用途。
• IL-8 receptor antagonists
  申请人：Palovich R. Michael

  公开号：US20060084661A1

  公开（公告）日：2006-04-20

  This invention relates to the novel use of amide squaramides in the treatment of disease states mediated by the chemokine, Interleukin-8 (IL-8).

  本发明涉及酰胺方酰胺在治疗由趋化因子Interleukin-8（IL-8）介导的疾病状态中的新用途。
• 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.
• EP1357909A4
  申请人：——

  公开号：EP1357909A4

  公开（公告）日：2006-01-04
• IL-8 RECEPTOR ANTAGONISTS
  申请人：SmithKline Beecham Corporation

  公开号：EP1357909A1

  公开（公告）日：2003-11-05