2-Anilino-5-aryloxazole 37

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-Anilino-5-aryloxazole 37
• 英文别名: N-(5-ethylsulfonyl-2-methoxyphenyl)-5-(3-thiophen-2-ylphenyl)-1,3-oxazol-2-amine
• 化学式: C₂₂H₂₀N₂O₄S₂
• 分子量: 440.544
• InChiKey: KOJNZGHIASJHCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-叠氮基-1-(3-溴苯基)乙酮 在 四(三苯基膦)钯 、 四丁基氯化铵 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 2-Anilino-5-aryloxazole 37
  参考文献：
  名称：

  Discovery and Evaluation of 2-Anilino-5-aryloxazoles as a Novel Class of VEGFR2 Kinase Inhibitors

  摘要：

  A series of derivatives of 2-anilino-5-phenyloxazole (5) has been identified as inhibitors of VEGFR2 kinase. Herein we describe the structure-activity relationship (SAR) of this novel template. Optimization of both aryl rings led to very potent inhibitors at both the enzymatic and cellular levels. Oxazole 39 had excellent solubility and good oral PK when dosed as the bis-mesylate salt and demonstrated moderate in vivo efficacy against HT29 human colon tumor xenografts. X-ray crystallography confirmed the proposed binding mode, and comparison of oxazoles 39 and 46 revealed interesting differences in orientation of 2-pyridyl and 3-pyridyl rings, respectively, attached at the meta position of the 5-phenyl ring.

  DOI：

  10.1021/jm049538w

文献信息

• Chemical compounds
  申请人：Brown Lee Matthew

  公开号：US20050288515A1

  公开（公告）日：2005-12-29

  Oxazole derivatives, which are useful as VEGFR2, CDK2, and CDK4 inhibitors are described herein. The described invention also includes methods of making such oxazole derivatives as well as methods of using the same in the treatment of hyperproliferative diseases.

  本文介绍了一种作为VEGFR2、CDK2和CDK4抑制剂有用的噁唑衍生物。所述发明还包括制备此类噁唑衍生物的方法以及在治疗增生性疾病中使用它们的方法。
• CHEMICAL COMPOUNDS
  申请人：Brown Lee Matthew

  公开号：US20070142437A1

  公开（公告）日：2007-06-21

  Oxazole derivatives, which are useful as VEGFR2, CDK2, and CDK4 inhibitors are described herein. The described invention also includes methods of making such oxazole derivatives as well as methods of using the same in the treatment of hyperproliferative diseases.

  本文描述了一种有用的噁唑衍生物，可作为VEGFR2、CDK2和CDK4抑制剂。所述发明还包括制备这种噁唑衍生物的方法，以及在治疗高增殖性疾病方面使用它们的方法。
• US7189712B2
  申请人：——

  公开号：US7189712B2

  公开（公告）日：2007-03-13
• Discovery and Evaluation of 2-Anilino-5-aryloxazoles as a Novel Class of VEGFR2 Kinase Inhibitors
  作者：Philip A. Harris、Mui Cheung、Robert N. Hunter、Matthew L. Brown、James M. Veal、Robert T. Nolte、Liping Wang、Wendy Liu、Renae M. Crosby、Jennifer H. Johnson、Andrea H. Epperly、Rakesh Kumar、Deirdre K. Luttrell、Jeffrey A. Stafford

  DOI：10.1021/jm049538w

  日期：2005.3.1

  A series of derivatives of 2-anilino-5-phenyloxazole (5) has been identified as inhibitors of VEGFR2 kinase. Herein we describe the structure-activity relationship (SAR) of this novel template. Optimization of both aryl rings led to very potent inhibitors at both the enzymatic and cellular levels. Oxazole 39 had excellent solubility and good oral PK when dosed as the bis-mesylate salt and demonstrated moderate in vivo efficacy against HT29 human colon tumor xenografts. X-ray crystallography confirmed the proposed binding mode, and comparison of oxazoles 39 and 46 revealed interesting differences in orientation of 2-pyridyl and 3-pyridyl rings, respectively, attached at the meta position of the 5-phenyl ring.