{5-[3,4-Difluoro-2-(2-fluoro-4-iodo-phenylamino)-phenyl]-[1,3,4]oxadiazol-2-yl}-(3-methoxy-propyl)-amine | 718618-10-1

• 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: {5-[3,4-Difluoro-2-(2-fluoro-4-iodo-phenylamino)-phenyl]-[1,3,4]oxadiazol-2-yl}-(3-methoxy-propyl)-amine
• 英文别名: 5-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]-N-(3-methoxypropyl)-1,3,4-oxadiazol-2-amine
• CAS: 718618-10-1
• 化学式: C₁₈H₁₆F₃IN₄O₂
• 分子量: 504.25
• InChiKey: PVARYTONZNVPEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  72.2
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-(3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoyl)-N-(3-methoxypropyl)hydrazine-1-carboxamide 在 三乙胺 、 三苯基膦 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 生成 {5-[3,4-Difluoro-2-(2-fluoro-4-iodo-phenylamino)-phenyl]-[1,3,4]oxadiazol-2-yl}-(3-methoxy-propyl)-amine
  参考文献：
  名称：

  2-Alkylamino- and alkoxy-substituted 2-amino-1,3,4-oxadiazoles—O-Alkyl benzohydroxamate esters replacements retain the desired inhibition and selectivity against MEK (MAP ERK kinase)

  摘要：

  This paper reports a second generation MEK inhibitor. The previously reported potent and efficacious MEK inhibitor, PD-184352 (CI-1040), contains an integral hydroxamate moiety. This compound suffered from less than ideal solubility and metabolic stability. An oxadiazole moiety behaves as a bioisostere for the hydroxamate group, leading to a more metabolically stable and efficacious MEK inhibitor.

  DOI：

  10.1016/j.bmcl.2008.10.015

文献信息

• MEK inhibiting compounds
  申请人：Barrett D. Stephen

  公开号：US20050004186A1

  公开（公告）日：2005-01-06

  This invention provides substituted Phenyl-(2-[1,3,4]thiadiazol-2-yl-phenyl)-amine and (2-[1,3,4]Oxadiazol-2-yl-phenyl)phenyl-amine compounds which act as inhibitors of MAPK/ERK Kinase (“MEK”) enzymes and pharmaceutical compositions and methods for their use in immunomodulation and in the treatment and alleviation of inflammation, and proliferative diseases such as cancer and restenosis.

  本发明提供了取代苯基-(2-[1,3,4]噻二唑-2-基苯基)-胺和(2-[1,3,4]噁二唑-2-基苯基)苯基胺化合物，其作为MAPK/ERK激酶（“MEK”）酶的抑制剂，并提供了在免疫调节和治疗和缓解炎症、癌症和再狭窄等增殖性疾病中使用它们的制药组合物和方法。
• 2-Alkylamino- and alkoxy-substituted 2-amino-1,3,4-oxadiazoles—O-Alkyl benzohydroxamate esters replacements retain the desired inhibition and selectivity against MEK (MAP ERK kinase)
  作者：Joseph S. Warmus、Cathlin Flamme、Lu Yan Zhang、Stephen Barrett、Alexander Bridges、Huifen Chen、Richard Gowan、Michael Kaufman、Judy Sebolt-Leopold、Wilbur Leopold、Ronald Merriman、Jeffrey Ohren、Alexander Pavlovsky、Sally Przybranowski、Haile Tecle、Heather Valik、Christopher Whitehead、Erli Zhang

  DOI：10.1016/j.bmcl.2008.10.015

  日期：2008.12

  This paper reports a second generation MEK inhibitor. The previously reported potent and efficacious MEK inhibitor, PD-184352 (CI-1040), contains an integral hydroxamate moiety. This compound suffered from less than ideal solubility and metabolic stability. An oxadiazole moiety behaves as a bioisostere for the hydroxamate group, leading to a more metabolically stable and efficacious MEK inhibitor.