ethyl 3-[[benzyl-[2-[[(2S)-1-[3-[3-[3-[[(2S)-2-[[2-[benzyl-[[8-[(2,6-difluorophenyl)methyl]-6-ethoxycarbonyl-2-[4-(ethylcarbamoylamino)phenyl]-5-oxoimidazo[1,2-a]pyrimidin-3-yl]methyl]amino]acetyl]amino]-3-methylbutanoyl]amino]prop-1-ynyl]phenyl]prop-2-ynylamino]-3-methyl-1-oxobutan-2-yl]amino]-2-oxoethyl]amino]methyl]-8-[(2,6-difluorophenyl)methyl]-2-[4-(ethylcarbamoylamino)phenyl]-5-oxoimidazo[1,2-a]pyrimidine-6-carboxylate | 1032417-64-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: ethyl 3-[[benzyl-[2-[[(2S)-1-[3-[3-[3-[[(2S)-2-[[2-[benzyl-[[8-[(2,6-difluorophenyl)methyl]-6-ethoxycarbonyl-2-[4-(ethylcarbamoylamino)phenyl]-5-oxoimidazo[1,2-a]pyrimidin-3-yl]methyl]amino]acetyl]amino]-3-methylbutanoyl]amino]prop-1-ynyl]phenyl]prop-2-ynylamino]-3-methyl-1-oxobutan-2-yl]amino]-2-oxoethyl]amino]methyl]-8-[(2,6-difluorophenyl)methyl]-2-[4-(ethylcarbamoylamino)phenyl]-5-oxoimidazo[1,2-a]pyrimidine-6-carboxylate
• CAS: 1032417-64-3
• 化学式: C₉₂H₉₄F₄N₁₆O₁₂
• 分子量: 1691.85
• InChiKey: UGPPSVMOASBBPU-LKVPSEKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  124
• 可旋转键数：
  38
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  334
• 氢给体数：
  8
• 氢受体数：
  22

反应信息

• 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 、 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 16.0h， 以3.56 mg的产率得到ethyl 3-[[benzyl-[2-[[(2S)-1-[3-[3-[3-[[(2S)-2-[[2-[benzyl-[[8-[(2,6-difluorophenyl)methyl]-6-ethoxycarbonyl-2-[4-(ethylcarbamoylamino)phenyl]-5-oxoimidazo[1,2-a]pyrimidin-3-yl]methyl]amino]acetyl]amino]-3-methylbutanoyl]amino]prop-1-ynyl]phenyl]prop-2-ynylamino]-3-methyl-1-oxobutan-2-yl]amino]-2-oxoethyl]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 homodimeric GnRHR antagonists having a rigid bis-propargylated benzene core

  摘要：

  The fact that GPCRs might function in a dimeric fashion is currently well accepted. For GnRHR, a GPCR that regulates gonadotropin release, there is evidence that the receptor also functions as a dimer. We here describe the design and synthesis of a set of dimeric GnRHR antagonists in order to understand the interaction of dimeric ligands to the receptor and to address the question whether GnRHR dimerisation is a prerequisite for signalling. Biological evaluation of the compounds shows no discrimination between monomeric and dimeric ligands in respect to binding affinities, however, the dimeric ligands appear to have different functional properties. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.01.054

文献信息

• Synthesis and evaluation of homodimeric GnRHR antagonists having a rigid bis-propargylated benzene core
  作者：Kimberly M. Bonger、Richard J.B.H.N. van den Berg、Annemiek D. Knijnenburg、Laura H. Heitman、Ad P. IJzerman、Julia Oosterom、Cornelis M. Timmers、Herman S. Overkleeft、Gijsbert A. van der Marel

  DOI：10.1016/j.bmc.2008.01.054

  日期：2008.4.1

  The fact that GPCRs might function in a dimeric fashion is currently well accepted. For GnRHR, a GPCR that regulates gonadotropin release, there is evidence that the receptor also functions as a dimer. We here describe the design and synthesis of a set of dimeric GnRHR antagonists in order to understand the interaction of dimeric ligands to the receptor and to address the question whether GnRHR dimerisation is a prerequisite for signalling. Biological evaluation of the compounds shows no discrimination between monomeric and dimeric ligands in respect to binding affinities, however, the dimeric ligands appear to have different functional properties. (C) 2008 Elsevier Ltd. All rights reserved.