methyl 5(6)-(4-aminophenoxy)benzimidazole-2-carbamate | 56073-92-8

• 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-aminophenoxy)benzimidazole-2-carbamate
• 英文别名: methyl 5(6)-(4-aminophenoxy)-2-benzimidazolyl carbamate；methyl (5-(4-aminophenoxy)-1H-benzimidazol-2-yl)carbamate；[5-(4-amino-phenoxy)-1(3)H-benzoimidazol-2-yl]-carbamic acid methyl ester；methyl N-[6-(4-aminophenoxy)-1H-benzimidazol-2-yl]carbamate
• CAS: 56073-92-8
• 化学式: C₁₅H₁₄N₄O₃
• 分子量: 298.301
• InChiKey: VOICTPRBLMDKHL-UHFFFAOYSA-N

物化性质

• 熔点：
  292 °C
• 密度：
  1.438±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  102
• 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-aminophenoxy)benzimidazole-2-carbamate 生成 methyl N-(5-(4-((2-fluoro-5-(trifluoromethyl)phenyl)aminocarbonylamino)phenylcarbonyl)-1H-benzimidazol-2-yl)carbamate
  参考文献：
  名称：

  Chemical compounds

  摘要：

  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，以及在治疗过度增殖性疾病中使用它们的方法。

  公开号：

  US20040082583A1
• 作为产物：
  描述：

  对乙酰氨基酚 在 盐酸 、 sodium dithionite 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 methyl 5(6)-(4-aminophenoxy)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

• [EN] PREPARATION AND METHODS OF USE FOR ORTHO-ARYL 5- MEMBERED HETEROARYL-CARBOXAMIDE CONTAINING MULTI-TARGETED KINASE INHIBITORS<br/>[FR] PRÉPARATION ET PROCÉDÉS D'UTILISATION D'ORTHO-ARYLE HÉTÉROARYLE À 5 CHAÎNONS -CARBOXAMIDE CONTENANT DES INHIBITEURS DE KINASES MULTICIBLES
  申请人：FLYNN GARY A

  公开号：WO2013022766A1

  公开（公告）日：2013-02-14

  The present disclosure relates to compounds of the Formula (I): and pharmaceutically acceptable salts, as kinase modulators, compatible with the Type-II inhibition of kinases.

  本公开涉及式(I)的化合物及其药用可接受盐，作为激酶调节剂，与激酶的II型抑制相兼容。
• 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。
• PREPARATION AND METHODS OF USE FOR ORTHO-ARYL 5-MEMBERED HETEROARYL-CARBOXAMIDE CONTAINING MULTI-TARGETED KINASE INHIBITORS
  申请人：Flynn Gary A.

  公开号：US20140228367A1

  公开（公告）日：2014-08-14

  The present disclosure relates to compounds of the Formula (I): and pharmaceutically acceptable salts, as kinase modulators, compatible with the Type-II inhibition of kinases.

  本公开涉及式（I）的化合物及其药学上可接受的盐，作为酶调节剂，与激酶的II型抑制相兼容。
• 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：——
• Synthesis of Methyl 5(6)-(4-Aminophenoxy)- and 5(6)-(2-Aminophenoxy)-2-benzimidazolyl Carbamates and Their Biological Properties
  作者：V. S. Pilyugin、A. N. Mikhailyuk、V. M. Kosareva、G. E. Chikisheva、G. V. Kiseleva、S. L. Kuznetsova、T. P. Vorobyeva、E. V. Klimakova

  DOI：10.1023/b:rujo.0000010185.19571.76

  日期：2003.8

  A procedure was developed for preparation of methyl 5(6)-(4-aminophenoxy)- and 5(6)-(2-aminophenoxy)-2-benzimidazolyl carbamates by reaction of 3,4,4'-triaminodiphenyl or 3,4,2'-triaminodiphenyl ethers respectively with methyl cyanocarbamate in water solution in the presence of 7-10 molar excess of acetic acid. The helminthicidal properties, embryotoxicity, and overall toxicity of compounds obtained were estimated.