Ethyl 3-[[benzyl-[2-oxo-2-(prop-2-ynylamino)ethyl]amino]methyl]-8-[(2,6-difluorophenyl)methyl]-2-[4-(ethylcarbamoylamino)phenyl]-5-oxoimidazo[1,2-a]pyrimidine-6-carboxylate | 942612-44-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Ethyl 3-[[benzyl-[2-oxo-2-(prop-2-ynylamino)ethyl]amino]methyl]-8-[(2,6-difluorophenyl)methyl]-2-[4-(ethylcarbamoylamino)phenyl]-5-oxoimidazo[1,2-a]pyrimidine-6-carboxylate
• CAS: 942612-44-4
• 化学式: C₃₈H₃₇F₂N₇O₅
• 分子量: 709.752
• InChiKey: XPULMKWNGQNTJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  138
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Ethyl 3-[[benzyl-[2-oxo-2-(prop-2-ynylamino)ethyl]amino]methyl]-8-[(2,6-difluorophenyl)methyl]-2-[4-(ethylcarbamoylamino)phenyl]-5-oxoimidazo[1,2-a]pyrimidine-6-carboxylate 、 1,8-二叠氮基-3,5-二氧杂辛烷 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 乙腈 、 叔丁醇 为溶剂， 以45%的产率得到Ethyl 3-[[[2-[[1-[2-[2-(2-azidoethoxy)ethoxy]ethyl]triazol-4-yl]methylamino]-2-oxoethyl]-benzylamino]methyl]-8-[(2,6-difluorophenyl)methyl]-2-[4-(ethylcarbamoylamino)phenyl]-5-oxoimidazo[1,2-a]pyrimidine-6-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of homo-bivalent GnRHR ligands

  摘要：

  G protein coupled receptors (GPCRs) are important drug targets in pharmaceutical research. Traditionally, most research efforts have been devoted towards the design of small molecule agonists and antagonists. An interesting, yet poorly investigated class of GPCR modulators comprise the bivalent ligands, in which two receptor pharmacophores are incorporated. Here, we set out to develop a general strategy for the synthesis of bivalent compounds that are projected to bind to the human gonadotropin-releasing hormone receptor (GnRHR). Our results on the dimerisation of a known GnRHR antagonist, with as key step the Huisgen 1,3-cycloaddition, and their ability to bind to and antagonize GnRH-induced GnRHR stimulation, are presented here. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.065
• 作为产物：
  描述：

  2-(N-((6-(ethoxycarbonyl)-8-(2,6-difluorobenzyl)-2-(4-(3-ethylureido)phenyl)-5,8-dihydro-5-oxoimidazo[1,2-a]pyrimidin-3-yl)methyl)-N-benzylamino)acetic acid 、 炔丙胺 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以54%的产率得到Ethyl 3-[[benzyl-[2-oxo-2-(prop-2-ynylamino)ethyl]amino]methyl]-8-[(2,6-difluorophenyl)methyl]-2-[4-(ethylcarbamoylamino)phenyl]-5-oxoimidazo[1,2-a]pyrimidine-6-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of homo-bivalent GnRHR ligands

  摘要：

  G protein coupled receptors (GPCRs) are important drug targets in pharmaceutical research. Traditionally, most research efforts have been devoted towards the design of small molecule agonists and antagonists. An interesting, yet poorly investigated class of GPCR modulators comprise the bivalent ligands, in which two receptor pharmacophores are incorporated. Here, we set out to develop a general strategy for the synthesis of bivalent compounds that are projected to bind to the human gonadotropin-releasing hormone receptor (GnRHR). Our results on the dimerisation of a known GnRHR antagonist, with as key step the Huisgen 1,3-cycloaddition, and their ability to bind to and antagonize GnRH-induced GnRHR stimulation, are presented here. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.065

文献信息

• Synthesis and evaluation of homo-bivalent GnRHR ligands
  作者：Kimberly M. Bonger、Richard J.B.H.N. van den Berg、Laura H. Heitman、Ad P. IJzerman、Julia Oosterom、Cornelis M. Timmers、Herman S. Overkleeft、Gijsbert A. van der Marel

  DOI：10.1016/j.bmc.2007.04.065

  日期：2007.7

  G protein coupled receptors (GPCRs) are important drug targets in pharmaceutical research. Traditionally, most research efforts have been devoted towards the design of small molecule agonists and antagonists. An interesting, yet poorly investigated class of GPCR modulators comprise the bivalent ligands, in which two receptor pharmacophores are incorporated. Here, we set out to develop a general strategy for the synthesis of bivalent compounds that are projected to bind to the human gonadotropin-releasing hormone receptor (GnRHR). Our results on the dimerisation of a known GnRHR antagonist, with as key step the Huisgen 1,3-cycloaddition, and their ability to bind to and antagonize GnRH-induced GnRHR stimulation, are presented here. (c) 2007 Elsevier Ltd. All rights reserved.