7-(cyanomethyl)-N-methylisoquinoline-3-carboxamide | 864237-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 7-(cyanomethyl)-N-methylisoquinoline-3-carboxamide
• CAS: 864237-09-2
• 化学式: C₁₃H₁₁N₃O
• 分子量: 225.25
• InChiKey: YMXJATPHLGUSIH-UHFFFAOYSA-N

物化性质

• 沸点：
  547.5±35.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-(cyanomethyl)-N-methylisoquinoline-3-carboxamide 在 氨 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 20.0~45.0 ℃ 、500.01 kPa 条件下， 反应 24.0h， 生成 7-{2-[3-(4-trifluoromethyl-phenyl)-ureido]-ethyl}-isoquinoline-3-carboxylic acid methylamide
  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：

  7-vinyl-isoquinoline-3-carboxylic acid methyl amide 在 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 氯化亚砜 作用下， 以 N-甲基吡咯烷酮 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 丙酮 为溶剂， 反应 29.5h， 生成 7-(cyanomethyl)-N-methylisoquinoline-3-carboxamide
  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] ISOQUINOLINE DERIVATIVES<br/>[FR] DERIVES DE L'ISOQUINOLINE
  申请人：MERCK PATENT GMBH

  公开号：WO2005082858A3

  公开（公告）日：2005-11-10
• Isoquinoline derivatives
  申请人：Buchstaller Hans-Peter

  公开号：US20070191423A1

  公开（公告）日：2007-08-16

  The present invention relates to isoquinoline derivatives of formula (I), 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.