1-[2-(4-Amino-3-nitrophenyl)ethyl]-3-[2-methoxy-5-(trifluoromethyl)phenyl]urea | 863910-65-0

• 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: 1-[2-(4-Amino-3-nitrophenyl)ethyl]-3-[2-methoxy-5-(trifluoromethyl)phenyl]urea
• CAS: 863910-65-0
• 化学式: C₁₇H₁₇F₃N₄O₄
• 分子量: 398.342
• InChiKey: YOLCHKMXIXUNQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[2-(4-Amino-3-nitrophenyl)ethyl]-3-[2-methoxy-5-(trifluoromethyl)phenyl]urea 在 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 9.0h， 生成 1-[2-methoxy-5-(trifluoromethyl)phenyl]-3-[2-[2-(trichloromethyl)-3H-benzimidazol-5-yl]ethyl]urea
  参考文献：
  名称：

  Design and synthesis of isoquinolines and benzimidazoles as RAF kinase inhibitors

  摘要：

  RAF kinase plays a critical role in the RAF-MEK-ERK signaling pathway and inhibitors of RAF could be of use for the treatment of various cancer types. We have designed potent RAF-1 inhibitors bearing novel bicyclic heterocycles as key structural elements for the interaction with the hinge region. In both series exploration of the SAR was focussed on the substitution of the phenyl ring, which binds to the induced fit pocket. Overall, it was confirmed that incorporation of lipophilic substituents was needed for potent Raf inhibition and a number of potent analogues were obtained. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.108
• 作为产物：
  描述：

  4-<2-(acetamido)ethyl>-2-nitro-acetanilide 在 盐酸 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 1-[2-(4-Amino-3-nitrophenyl)ethyl]-3-[2-methoxy-5-(trifluoromethyl)phenyl]urea
  参考文献：
  名称：

  Design and synthesis of isoquinolines and benzimidazoles as RAF kinase inhibitors

  摘要：

  RAF kinase plays a critical role in the RAF-MEK-ERK signaling pathway and inhibitors of RAF could be of use for the treatment of various cancer types. We have designed potent RAF-1 inhibitors bearing novel bicyclic heterocycles as key structural elements for the interaction with the hinge region. In both series exploration of the SAR was focussed on the substitution of the phenyl ring, which binds to the induced fit pocket. Overall, it was confirmed that incorporation of lipophilic substituents was needed for potent Raf inhibition and a number of potent analogues were obtained. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.108

文献信息

• [EN] BENZIMIDAZOLYL DERIVATIVES AS KINASE INHIBITORS<br/>[FR] DERIVES DE BENZIMIDAZOLYLE
  申请人：MERCK PATENT GMBH

  公开号：WO2005082862A3

  公开（公告）日：2005-12-01
• Benzimidazolyl derivatives
  申请人：Buchstaller Hans-Peter

  公开号：US20070191444A1

  公开（公告）日：2007-08-16

  The present invention relates to benzimidazolyl derivatives of formula (I), with the definition of R 8 , p , Ar 1 , E, D, R 9 , q and R 10 according to claim 1 , the use of the compounds of formula (I) as inhibitors of one or more kinases, the use of the compounds of formula (I) for the manufacture of a pharmaceutical composition and a method of treatment, comprising administering said pharmaceutical composition to a patient.
• Design and synthesis of isoquinolines and benzimidazoles as RAF kinase inhibitors
  作者：Hans-Peter Buchstaller、Lars Burgdorf、Dirk Finsinger、Frank Stieber、Christian Sirrenberg、Christiane Amendt、Matthias Grell、Frank Zenke、Mireille Krier

  DOI：10.1016/j.bmcl.2011.02.108

  日期：2011.4

  RAF kinase plays a critical role in the RAF-MEK-ERK signaling pathway and inhibitors of RAF could be of use for the treatment of various cancer types. We have designed potent RAF-1 inhibitors bearing novel bicyclic heterocycles as key structural elements for the interaction with the hinge region. In both series exploration of the SAR was focussed on the substitution of the phenyl ring, which binds to the induced fit pocket. Overall, it was confirmed that incorporation of lipophilic substituents was needed for potent Raf inhibition and a number of potent analogues were obtained. (C) 2011 Elsevier Ltd. All rights reserved.