2-(4-fluoroethyloxybenzyl)-4-(cis-3a,4,5,6,7,7a-hexahydroisoindolin-2-yl)-4-oxobutanoic acid | 1245944-86-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-(4-fluoroethyloxybenzyl)-4-(cis-3a,4,5,6,7,7a-hexahydroisoindolin-2-yl)-4-oxobutanoic acid
• CAS: 1245944-86-8
• 化学式: C₂₁H₂₈FNO₄
• 分子量: 377.456
• InChiKey: CTBSNEFZOGMTAX-KSZLIROESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (S)-2-(benzylamino)-2-oxo-1-phenylethyl (S)-2-(4-(2-fluoroethoxy)benzyl)-4-((3aR,7aS)-octahydro-2H-isoindol-2-yl)-4-oxobutanoate 在 甲醇 、 sodium hydroxide 作用下， 生成 2-(4-fluoroethyloxybenzyl)-4-(cis-3a,4,5,6,7,7a-hexahydroisoindolin-2-yl)-4-oxobutanoic acid
  参考文献：
  名称：

  EP2407455

  摘要：

  公开号：

文献信息

• Synthesis and evaluation of 18F-labeled mitiglinide derivatives as positron emission tomography tracers for β-cell imaging
  作者：Hiroyuki Kimura、Hirokazu Matsuda、Hiroyuki Fujimoto、Kenji Arimitsu、Kentaro Toyoda、Eri Mukai、Hiroshi Nakamura、Yu Ogawa、Mikako Takagi、Masahiro Ono、Nobuya Inagaki、Hideo Saji

  DOI：10.1016/j.bmc.2014.04.059

  日期：2014.7

  Measuring changes in beta-cell mass in vivo during progression of diabetes mellitus is important for understanding the pathogenesis, facilitating early diagnosis, and developing novel therapeutics for this disease. However, a non-invasive method has not been developed. A novel series of mitiglinide derivatives (o-FMIT, m-FMIT and p-FMIT; FMITs) were synthesized and their binding affinity for the sulfonylurea receptor 1 (SUR1) of pancreatic islets were evaluated by inhibition studies. (+)-(S)-o-FMIT had the highest affinity of our synthesized FMITs (IC50 = 1.8 mu M). (+)-(S)-o-[F-18]FMIT was obtained with radiochemical yield of 18% by radiofluorination of racemic precursor 7, hydrolysis, and optical resolution with chiral HPLC; its radiochemical purity was >99%. In biodistribution experiments using normal mice, (+)-(S)-o-[F-18]FMIT showed 1.94 +/- 0.42% ID/g of pancreatic uptake at 5 min p.i., and decreases in radioactivity in the liver (located close to the pancreas) was relatively rapid. Ex vivo autoradiography experiments using pancreatic sections confirmed accumulation of (+)-(S)-o-[F-18]FMIT in pancreatic beta-cells. These results suggest that (+)-(S)-o-[F-18]FMIT meets the basic requirements for an radiotracer, and could be a candidate positron emission tomography tracer for in vivo imaging of pancreatic beta-cells. (C) 2014 Elsevier Ltd. All rights reserved.
• EP2407455
  申请人：——

  公开号：——

  公开（公告）日：——