3-(3,4-dioxo-2-(phenylamino)cyclobut-1-enylamino)-2-hydroxy-N,N-dimethylbenzamide

• 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: 3-(3,4-dioxo-2-(phenylamino)cyclobut-1-enylamino)-2-hydroxy-N,N-dimethylbenzamide
• 英文别名: 3-[(2-anilino-3,4-dioxocyclobuten-1-yl)amino]-2-hydroxy-N,N-dimethylbenzamide
• 化学式: C₁₉H₁₇N₃O₄
• 分子量: 351.362
• InChiKey: UJNRJTAYSRLEJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  98.7
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-硝基水杨酸 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 3-(3,4-dioxo-2-(phenylamino)cyclobut-1-enylamino)-2-hydroxy-N,N-dimethylbenzamide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 3,4-diaminocyclobut-3-ene-1,2-dione CXCR2 antagonists

  摘要：

  A novel series of 3,4-diaminocyclobut-3-ene-1,2-diones was prepared and found to show potent inhibitory activity of CXCR2 binding and IL-8-mediated chemotaxis of a CXCR2-expressing cell line. Microsome stability and Caco2 studies were subsequently used to show that compounds of this chemotype are predicted to have good oral bioavailability and are thus suitable for pharmaceutical development. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.082

文献信息

• Treatment of chemokine mediated diseases
  申请人：Taveras G. Arthur

  公开号：US20070155756A1

  公开（公告）日：2007-07-05

  Methods of treating chemokine-mediated diseases are disclosed. The methods comprise the administration of CXC-Chemokine receptor antagonists of the formula or pharmaceutically acceptable salts or solvates thereof, in combination with other classes of pharmaceutical compounds. The chemokine-mediated diseases include acute and chronic inflammatory disorders, psoriasis, cystic fibrosis, asthma and cancer. Also disclosed are novel compounds of formula (I).

  本发明揭示了治疗趋化因子介导疾病的方法。该方法包括给予以下公式的CXC趋化因子受体拮抗剂或其药学上可接受的盐或溶剂，与其他类别的药物化合物结合使用。趋化因子介导的疾病包括急性和慢性炎症性疾病、银屑病、囊性纤维化、哮喘和癌症。本发明还揭示了公式（I）的新化合物。
• COMBINATION TREATMENTS FOR CHEMOKINE-MEDIATED DISEASES
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP1485089B1

  公开（公告）日：2013-04-17
• US7960433B2
  申请人：——

  公开号：US7960433B2

  公开（公告）日：2011-06-14
• Synthesis and structure–activity relationships of 3,4-diaminocyclobut-3-ene-1,2-dione CXCR2 antagonists
  作者：J. Robert Merritt、Laura L. Rokosz、Kingsley H. Nelson、Bernd Kaiser、Wei Wang、Tara M. Stauffer、Lynne E. Ozgur、Adriane Schilling、Ge Li、John J. Baldwin、Arthur G. Taveras、Michael P. Dwyer、Jianping Chao

  DOI：10.1016/j.bmcl.2006.04.082

  日期：2006.8

  A novel series of 3,4-diaminocyclobut-3-ene-1,2-diones was prepared and found to show potent inhibitory activity of CXCR2 binding and IL-8-mediated chemotaxis of a CXCR2-expressing cell line. Microsome stability and Caco2 studies were subsequently used to show that compounds of this chemotype are predicted to have good oral bioavailability and are thus suitable for pharmaceutical development. (c) 2006 Elsevier Ltd. All rights reserved.