5-methyl-3-[4-(3-phenylallyl)-piperazin-1-ylmethyl]-3,3a,4,5-tetrahydroisoxazolo[4,3-c]quinoline | 1042685-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-methyl-3-[4-(3-phenylallyl)-piperazin-1-ylmethyl]-3,3a,4,5-tetrahydroisoxazolo[4,3-c]quinoline
• 英文别名: 5-methyl-3-[[4-(3-phenylprop-2-enyl)piperazin-1-yl]methyl]-3a,4-dihydro-3H-[1,2]oxazolo[4,3-c]quinoline
• CAS: 1042685-40-4
• 化学式: C₂₅H₃₀N₄O
• 分子量: 402.539
• InChiKey: GHPKBFZQNLPFFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  31.31
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 3-((4-(3-phenylallyl)piperazin-1-yl)methyl)-3,3a,4,5-tetrahydroisoxazolo[4,3-c]quinoline 在 sodium cyanoborohydride 、 zinc dibromide 作用下， 以 甲醇 为溶剂， 以40%的产率得到5-methyl-3-[4-(3-phenylallyl)-piperazin-1-ylmethyl]-3,3a,4,5-tetrahydroisoxazolo[4,3-c]quinoline
  参考文献：
  名称：

  Synthesis and in vivo evaluation of [11C]MPTQ: A potential PET tracer for alpha2A-adrenergic receptors

  摘要：

  Radiosynthesis and in vivo evaluation of [N-methyl-C-11] 5-methyl-3-[4-(3-phenylallyl)-piperazin-1-ylmethyl]-3,3a,4,5-tetrahydroisoxazolo[4,3-c] quinoline (1), a potential PET tracer for alpha2-adrenergic receptors is described. Syntheses of nonradioactive standard 1 and corresponding desmethyl precursor 2 were achieved from 2-aminobenzaldehyde in 40% and 65% yields, respectively. Methylation using [C-11]CH3I in presence of aqueous potassium hydroxide in DMSO afforded [C-11]1 in 25% yield (EOS) with > 99% chemical and radiochemical purities with a specific activity ranged from 3-4 Ci/mu mol (n = 6). The total synthesis time was 30 min from EOB. PET studies in anesthetized baboon show that [C-11]1 penetrates BBB and accumulates in alpha2A-AR enriched brain areas. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.099

文献信息

• Synthesis and in vivo evaluation of [11C]MPTQ: A potential PET tracer for alpha2A-adrenergic receptors
  作者：Jaya Prabhakaran、Vattoly J. Majo、Matthew S. Milak、Pratap Mali、Lyudmila Savenkova、J. John Mann、Ramin V. Parsey、J.S. Dileep Kumar

  DOI：10.1016/j.bmcl.2010.04.099

  日期：2010.6

  Radiosynthesis and in vivo evaluation of [N-methyl-C-11] 5-methyl-3-[4-(3-phenylallyl)-piperazin-1-ylmethyl]-3,3a,4,5-tetrahydroisoxazolo[4,3-c] quinoline (1), a potential PET tracer for alpha2-adrenergic receptors is described. Syntheses of nonradioactive standard 1 and corresponding desmethyl precursor 2 were achieved from 2-aminobenzaldehyde in 40% and 65% yields, respectively. Methylation using [C-11]CH3I in presence of aqueous potassium hydroxide in DMSO afforded [C-11]1 in 25% yield (EOS) with > 99% chemical and radiochemical purities with a specific activity ranged from 3-4 Ci/mu mol (n = 6). The total synthesis time was 30 min from EOB. PET studies in anesthetized baboon show that [C-11]1 penetrates BBB and accumulates in alpha2A-AR enriched brain areas. (C) 2010 Elsevier Ltd. All rights reserved.