6-chloro-2-hydroxy-3-nitrobenzonitrile | 201467-03-0

• 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-nitrobenzonitrile
• 英文别名: 6-Chlor-2-hydroxy-3-nitro-benzonitril；6-Chlor-5-nitro-2-hydroxy-benzoesaeure-nitril；2-nitro-5-chloro-6cyanophenol；2-Nitro-5-chloro-6-cyanophenol
• CAS: 201467-03-0
• 化学式: C₇H₃ClN₂O₃
• 分子量: 198.565
• InChiKey: RQVUJDXGDQGJEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-chloro-2-hydroxy-3-nitrobenzonitrile 在 乙醇 、 tin(ll) chloride 作用下， 反应 16.0h， 生成 2-hydroxy-3-cyano-4-chloroaniline
  参考文献：
  名称：

  Evaluation of Potent and Selective Small-Molecule Antagonists for the CXCR2 Chemokine Receptor

  摘要：

  N,N'-Diarylureas were prepared, and the structure-activity relationship relative to the CXCR2 receptor was examined. This led to the identification of a potent and highly selective CXCR2 antagonist, which in addition was shown to be functionally active both in vitro against human neutrophils and in vivo in rabbit models of ear edema and neutropenia.

  DOI：

  10.1021/jm034248l
• 作为产物：
  描述：

  2-氯-6-羟基苯腈 在 sodium nitrite sodium nitrate 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 以29.2%的产率得到6-chloro-2-hydroxy-3-nitrobenzonitrile
  参考文献：
  名称：

  IL-8 receptor antagonists

  摘要：

  新型IL-8受体拮抗剂及其使用方法。

  公开号：

  US06271261B1

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.
• Discovery of potent and orally bioavailable N,N′-diarylurea antagonists for the CXCR2 chemokine receptor
  作者：Qi Jin、Hong Nie、Brent W. McCleland、Katherine L. Widdowson、Michael R. Palovich、John D. Elliott、Richard M. Goodman、Miriam Burman、Henry M. Sarau、Keith W. Ward、Melanie Nord、Bonnie M. Orr、Peter D. Gorycki、Jakob Busch-Petersen

  DOI：10.1016/j.bmcl.2004.06.097

  日期：2004.9

  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.
• IL-8 RECEPTOR ANTAGONISTS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0915651A1

  公开（公告）日：1999-05-19
• EP0915651A4
  申请人：——

  公开号：EP0915651A4

  公开（公告）日：2001-10-24
• US6271261B1
  申请人：——

  公开号：US6271261B1

  公开（公告）日：2001-08-07