methyl 5(6)-(4-acetamidophenoxy)benzimidazole-2-carbamate | 56073-91-7

• 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: methyl 5(6)-(4-acetamidophenoxy)benzimidazole-2-carbamate
• 英文别名: [5-(4-acetylamino-phenoxy)-1(3)H-benzoimidazol-2-yl]-carbamic acid methyl ester；methyl N-[6-(4-acetamidophenoxy)-1H-benzimidazol-2-yl]carbamate
• CAS: 56073-91-7
• 化学式: C₁₇H₁₆N₄O₄
• 分子量: 340.338
• InChiKey: PXAXXXKUVRXFMQ-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：

  methyl 5(6)-(4-acetamidophenoxy)benzimidazole-2-carbamate 在 盐酸 作用下， 反应 0.5h， 以83.7%的产率得到methyl 5(6)-(4-aminophenoxy)benzimidazole-2-carbamate
  参考文献：
  名称：

  Abuzar, Syed; Sharma, Satyavan; Gupta, Suman, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 12, p. 1274 - 1278

  摘要：

  DOI：
• 作为产物：
  描述：

  对乙酰氨基酚 在 sodium dithionite 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 5(6)-(4-acetamidophenoxy)benzimidazole-2-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

文献信息

• CHEMICAL COMPOUNDS
  申请人：Cheung Mui

  公开号：US20070249600A1

  公开（公告）日：2007-10-25

  Benzimidazole derivatives, which are useful as TIE-2 and/or VEGFR2 inhibitors are described herein. The described invention also includes methods of making such benzimidazole derivatives as well as methods of using the same in the treatment of hyperproliferative diseases.

  本文描述了作为TIE-2和/或VEGFR2抑制剂有用的苯并咪唑衍生物。所述发明还包括制备这种苯并咪唑衍生物的方法，以及在治疗过度增生性疾病中使用它们的方法。
• US3965113A
  申请人：——

  公开号：US3965113A

  公开（公告）日：1976-06-22
• US7238813B2
  申请人：——

  公开号：US7238813B2

  公开（公告）日：2007-07-03
• Abuzar, Syed; Sharma, Satyavan; Gupta, Suman, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 12, p. 1274 - 1278
  作者：Abuzar, Syed、Sharma, Satyavan、Gupta, Suman、Misra, Anuradha、Katiyar, J. C.

  DOI：——

  日期：——
• Discovery of Novel Benzimidazoles as Potent Inhibitors of TIE-2 and VEGFR-2 Tyrosine Kinase Receptors
  作者：Masaichi Hasegawa、Naohiko Nishigaki、Yoshiaki Washio、Kazuya Kano、Philip A. Harris、Hideyuki Sato、Ichiro Mori、Rob I. West、Megumi Shibahara、Hiroko Toyoda、Liping Wang、Robert T. Nolte、James M. Veal、Mui Cheung

  DOI：10.1021/jm0611051

  日期：2007.9.1

  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.