[11C]-methyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-benzimidazole-7-carboxylate | 1203674-08-1

• 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: [11C]-methyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-benzimidazole-7-carboxylate
• 英文别名: [11C]methyl candesartan；(111C)methyl 2-ethoxy-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate
• CAS: 1203674-08-1
• 化学式: C₂₅H₂₂N₆O₃
• 分子量: 453.477
• InChiKey: RBPFEPGTRLLUKI-JVVVGQRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  [11C]methyl 2-ethoxy-1-[[2'-[n-(triphenylmethyl)-1H-tetrazol-5-yl]biphenyl-4-yl]methyl]-1H-benzimidazole-7-carboxylate 在 盐酸 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.03h， 生成 [11C]-methyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-benzimidazole-7-carboxylate
  参考文献：
  名称：

  Novel O-[11C]methylated derivatives of candesartan as angiotensin II AT1 receptor imaging ligands: Radiosynthesis and ex vivo evaluation in rats

  摘要：

  [C-11]Methyl-candesartan and its desethyl derivative ([C-11]TH4) were developed as potential radiotracers for imaging angiotensin II (Ang II) type 1 (AT(1)) receptors. These compounds were synthesized via methylation of tetrazole-protected candesartan using [C-11] methyl iodide followed by deprotection through HCl hydrolysis at 65 degrees C to produce [C-11]methyl-candesartan, and 90 degrees C for [C-11]TH4. Ex vivo biodistribution and competition studies were carried out for both [C-11]methyl-candesartan and [C-11]TH4 to assess tissue retention time course and binding selectivity. Besides the liver, [C-11]methyl-candesartan and [C-11]TH4 displayed highest tissue retention in the AT(1) receptor-rich renal cortex and outer medulla. At tracer doses 15 min post-injection, [C-11]methyl-candesartan demonstrated higher specific binding proportion for AT(1) receptors, and selectivity for AT(1) over Ang II AT(2), Mas, beta-adrenergic, and alpha(2)-adrenergic receptors in rat kidneys compared to [C-11]TH4. This study indicates that [C-11]methyl-candesartan has potential for in vivo imaging renal AT(1) receptors selectively using positron emission tomography. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.016