[5-(3-acetylamino-phenoxy)-1(3)H-benzoimidazol-2-yl]-carbamic acid methyl ester | 56073-97-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: [5-(3-acetylamino-phenoxy)-1(3)H-benzoimidazol-2-yl]-carbamic acid methyl ester
• 英文别名: methyl N-[6-(3-acetamidophenoxy)-1H-benzimidazol-2-yl]carbamate
• CAS: 56073-97-3
• 化学式: C₁₇H₁₆N₄O₄
• 分子量: 340.338
• InChiKey: LZUKRXWXSMBCSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [5-(3-acetylamino-phenoxy)-1(3)H-benzoimidazol-2-yl]-carbamic acid methyl ester 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 methyl N-(5-(3-((2-fluoro-5-(trifluoromethyl)phenyl)aminocarbonylamino)phenoxy)-1H-benzimidazol-2-yl)carbamate
  参考文献：
  名称：

  Discovery of Novel Benzimidazoles as Potent Inhibitors of TIE-2 and VEGFR-2 Tyrosine Kinase Receptors

  摘要：

  We herein disclose a novel chemical series of benzimidazole-ureas as inhibitors of VEGFR-2 and TIE-2 kinase receptors, both of which are implicated in angiogenesis. Structure-activity relationship (SAR) studies elucidated a critical role for the NI nitrogen of both the benzimidazole (segment E) and urea (segment B) moieties. The SAR results were also supported by the X-ray crystallographic elucidation of the role of the NI nitrogen and the urea moiety when the benzimidazole-urea compounds were bound to the VEGFR-2 enzyme. The left side phenyl ring (segment A) occupies the backpocket where a 3-hydrophobic substituent was favored for TIE-2 activity.

  DOI：

  10.1021/jm0611051
• 作为产物：
  描述：

  5-(3-acetamidophenoxy)-2-nitroaniline 在 sodium dithionite 作用下， 以 乙醇 为溶剂， 生成 [5-(3-acetylamino-phenoxy)-1(3)H-benzoimidazol-2-yl]-carbamic acid methyl ester
  参考文献：
  名称：

  Discovery of Novel Benzimidazoles as Potent Inhibitors of TIE-2 and VEGFR-2 Tyrosine Kinase Receptors

  摘要：

  We herein disclose a novel chemical series of benzimidazole-ureas as inhibitors of VEGFR-2 and TIE-2 kinase receptors, both of which are implicated in angiogenesis. Structure-activity relationship (SAR) studies elucidated a critical role for the NI nitrogen of both the benzimidazole (segment E) and urea (segment B) moieties. The SAR results were also supported by the X-ray crystallographic elucidation of the role of the NI nitrogen and the urea moiety when the benzimidazole-urea compounds were bound to the VEGFR-2 enzyme. The left side phenyl ring (segment A) occupies the backpocket where a 3-hydrophobic substituent was favored for TIE-2 activity.

  DOI：

  10.1021/jm0611051