N-(3-{3-[5-(4-methylpiperazin-1-yl)pent-1-yn-1-yl]pyrazolo[1,5-a]pyrimidin-7-yl}phenyl)-3-(trifluoromethyl)benzamide | 950736-15-9

• 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: N-(3-{3-[5-(4-methylpiperazin-1-yl)pent-1-yn-1-yl]pyrazolo[1,5-a]pyrimidin-7-yl}phenyl)-3-(trifluoromethyl)benzamide
• 英文别名: N-(3-(3-(5-(4-methylpiperazin-1-yl)pent-1-ynyl)pyrazolo[1,5-a]pyrimidin-7-yl)phenyl)-3-(trifluoromethyl)benzamide；N-[3-[3-[5-(4-methylpiperazin-1-yl)pent-1-ynyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-3-(trifluoromethyl)benzamide
• CAS: 950736-15-9
• 化学式: C₃₀H₂₉F₃N₆O
• 分子量: 546.595
• InChiKey: YIICPBQWCOBAJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-methyl-4-(pent-4-yn-1-yl)piperazine 、 N-[3-(3-bromo-pyrazolo[1,5-a]pyrimidin-7-yl)-phenyl]-3-trifluoromethyl-benzamide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 3.0h， 以25%的产率得到N-(3-{3-[5-(4-methylpiperazin-1-yl)pent-1-yn-1-yl]pyrazolo[1,5-a]pyrimidin-7-yl}phenyl)-3-(trifluoromethyl)benzamide
  参考文献：
  名称：

  Non-hinge-binding pyrazolo[1,5-a]pyrimidines as potent B-Raf kinase inhibitors

  摘要：

  As part of our research effort to discover B-Raf kinase inhibitors, we prepared a series of C-3 substituted N-(3-(pyrazolo[1,5-a]pyrimidin-7-yl)phenyl)-3-(trifluoromethyl)benzamides. X-ray crystallography studies revealed that one of the more potent inhibitors (10n) bound to B-Raf kinase without forming a hinge-binding hydrogen bond. With basicamine residues appended to C-3 aryl residues, cellular activity and solubility were enhanced over previously described compounds of this class. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.049

文献信息

• Pyrazolo[1,5-A]pyrimidine derivatives and methods of use thereof
  申请人：Gopalsamy Ariamala

  公开号：US20070219186A1

  公开（公告）日：2007-09-20

  The present invention relates to pyrazolo[1,5-a]pyrimidine derivatives, compositions comprising an effective amount of a pyrazolo[1,5-a]pyrimidine derivative and methods for treating or preventing cancer, comprising administering to a subject in need thereof an effective amount of a pyrazolo[1,5-a]pyrimidine derivative.

  本发明涉及吡唑并[1,5-a]嘧啶衍生物，包括有效量的吡唑并[1,5-a]嘧啶衍生物的组合物，以及治疗或预防癌症的方法，包括向需要的受试者施用有效量的吡唑并[1,5-a]嘧啶衍生物。
• PYRAZOLO[1,5-A]PYRIMIDINE DERIVATIVES AND METHODS OF USE THEREOF
  申请人：Wyeth

  公开号：EP1996594A2

  公开（公告）日：2008-12-03
• [EN] PYRAZOLO[1,5-A]PYRIMIDINE DERIVATIVES AND METHODS OF USE THEREOF<br/>[FR] DERIVES DE PYRAZOLO[1,5-A]PYRIMIDINE ET PROCEDES D'UTILISATION DE CEUX-CI
  申请人：WYETH CORP

  公开号：WO2007109093A2

  公开（公告）日：2007-09-27

  [EN] The present invention relates to pyrazolo[1,5-a]pyrimidine derivatives, compositions comprising an effective amount of a pyrazolo[1,5-a]pyrimidine derivative and methods for treating or preventing cancer, comprising administering to a subject in need thereof an effective amount of a pyrazolo[1,5-a]pyrimidine derivative.
  [FR] La présente invention concerne des dérivés de pyrazolo[1,5-a]pyrimidine, des compositions comprenant une quantité efficace d'un dérivé de pyrazolo[1,5-a]pyrimidine et des procédés pour le traitement ou la prévention du cancer, consistant à administrer une quantité efficace de dérivé de pyrazolo[1,5-a]pyrimidine à un sujet en ayant besoin.
• Non-hinge-binding pyrazolo[1,5-a]pyrimidines as potent B-Raf kinase inhibitors
  作者：Dan M. Berger、Nancy Torres、Minu Dutia、Dennis Powell、Greg Ciszewski、Ariamala Gopalsamy、Jeremy I. Levin、Kyung-Hee Kim、Weixin Xu、James Wilhelm、YongBo Hu、Karen Collins、Larry Feldberg、Steven Kim、Eileen Frommer、Donald Wojciechowicz、Robert Mallon

  DOI：10.1016/j.bmcl.2009.10.049

  日期：2009.12

  As part of our research effort to discover B-Raf kinase inhibitors, we prepared a series of C-3 substituted N-(3-(pyrazolo[1,5-a]pyrimidin-7-yl)phenyl)-3-(trifluoromethyl)benzamides. X-ray crystallography studies revealed that one of the more potent inhibitors (10n) bound to B-Raf kinase without forming a hinge-binding hydrogen bond. With basicamine residues appended to C-3 aryl residues, cellular activity and solubility were enhanced over previously described compounds of this class. (C) 2009 Elsevier Ltd. All rights reserved.