4-(1-methylpiperazinylacetyl)-4'-(4-methylpiperidinylacetyl)biphenyl | 259143-11-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(1-methylpiperazinylacetyl)-4'-(4-methylpiperidinylacetyl)biphenyl
• 英文别名: 1-[4-[4-[2-(4-Methylpiperazin-1-yl)acetyl]phenyl]phenyl]-2-(4-methylpiperidin-1-yl)ethanone
• CAS: 259143-11-8
• 化学式: C₂₇H₃₅N₃O₂
• 分子量: 433.594
• InChiKey: HKTMPJOXJATEAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(1-methylpiperazinylacetyl)-4'-(4-methylpiperidinylacetyl)biphenyl 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以59%的产率得到pipzA-4
  参考文献：
  名称：

  Synthesis of [18F]FA-4 and [11C]pipzA-4 as radioligands for the high affinity choline uptake system

  摘要：

  We have prepared two radiolabelled analogues of hemicholinium-3 (HC-3) as potential in vivo tracers of the sodium dependent high affinity choline uptake (SDHAChU) system. Thus, 4-[1-hydroxy-2-(4-[F-18] fluoromethylpiperidinyl)ethyl]-4'-[1-hydroxy-2-(4-methylpiperidinyl)ethyl] ([F-18]FA-4) and 4-[1-hydroxy-2-(4-[ C-11] methylpiperazinyl)ethyl]-4'-[1-hydroxy-2-(4-methylpiperidinyl)]biphenyl ([C-11]pipzA-4) have been synthesized. [F-18]FA-4 was prepared by reaction of 4-[F-18] fluoromethylpiperidine with 4-(alpha-bromoacetyl)-4'-(4-methylpiperidinyl acetyl)biphenyl followed by reduction of the keto groups to alcohols with: NaBH4. The total synthesis time was 300 minutes and [18F]FA-4 was Obtained with a specific activity of 5.6 GBq/mu mol (EOS) and an overall decay corrected radiochemical yield of 3.1+/-0.6%. [C-11]pipzA-4 was prepared by reaction of [C-11]methyl triflate with 4-[1 -hydroxy-2-piperazinyl)ethyl]-4'-[1-hydroxy-2-(4-methylpiperidinyl)ethyl]- biphenyl. The total synthesis time was 25 minutes and [C-11]pipzA-4 was obtained with:a specific activity of 13.7 GBq/mu mol (EOS) and an overall decay corrected radiochemical yield of 19.5+/-2.2%.

  DOI：

  10.1002/(sici)1099-1344(19991230)42:13<1289::aid-jlcr287>3.0.co;2-c
• 作为产物：
  描述：

  4,4'-二(2-溴乙酰基)联苯 在 盐酸 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 丙酮 、 甲苯 为溶剂， 反应 28.0h， 生成 4-(1-methylpiperazinylacetyl)-4'-(4-methylpiperidinylacetyl)biphenyl
  参考文献：
  名称：

  Synthesis of [18F]FA-4 and [11C]pipzA-4 as radioligands for the high affinity choline uptake system

  摘要：

  We have prepared two radiolabelled analogues of hemicholinium-3 (HC-3) as potential in vivo tracers of the sodium dependent high affinity choline uptake (SDHAChU) system. Thus, 4-[1-hydroxy-2-(4-[F-18] fluoromethylpiperidinyl)ethyl]-4'-[1-hydroxy-2-(4-methylpiperidinyl)ethyl] ([F-18]FA-4) and 4-[1-hydroxy-2-(4-[ C-11] methylpiperazinyl)ethyl]-4'-[1-hydroxy-2-(4-methylpiperidinyl)]biphenyl ([C-11]pipzA-4) have been synthesized. [F-18]FA-4 was prepared by reaction of 4-[F-18] fluoromethylpiperidine with 4-(alpha-bromoacetyl)-4'-(4-methylpiperidinyl acetyl)biphenyl followed by reduction of the keto groups to alcohols with: NaBH4. The total synthesis time was 300 minutes and [18F]FA-4 was Obtained with a specific activity of 5.6 GBq/mu mol (EOS) and an overall decay corrected radiochemical yield of 3.1+/-0.6%. [C-11]pipzA-4 was prepared by reaction of [C-11]methyl triflate with 4-[1 -hydroxy-2-piperazinyl)ethyl]-4'-[1-hydroxy-2-(4-methylpiperidinyl)ethyl]- biphenyl. The total synthesis time was 25 minutes and [C-11]pipzA-4 was obtained with:a specific activity of 13.7 GBq/mu mol (EOS) and an overall decay corrected radiochemical yield of 19.5+/-2.2%.

  DOI：

  10.1002/(sici)1099-1344(19991230)42:13<1289::aid-jlcr287>3.0.co;2-c

文献信息

• Synthesis of [18F]FA-4 and [11C]pipzA-4 as radioligands for the high affinity choline uptake system
  作者：C. Gilissen、G. Bormans、T. de Groot、A. Verbruggen

  DOI：10.1002/(sici)1099-1344(19991230)42:13<1289::aid-jlcr287>3.0.co;2-c

  日期：1999.12.30

  We have prepared two radiolabelled analogues of hemicholinium-3 (HC-3) as potential in vivo tracers of the sodium dependent high affinity choline uptake (SDHAChU) system. Thus, 4-[1-hydroxy-2-(4-[F-18] fluoromethylpiperidinyl)ethyl]-4'-[1-hydroxy-2-(4-methylpiperidinyl)ethyl] ([F-18]FA-4) and 4-[1-hydroxy-2-(4-[ C-11] methylpiperazinyl)ethyl]-4'-[1-hydroxy-2-(4-methylpiperidinyl)]biphenyl ([C-11]pipzA-4) have been synthesized. [F-18]FA-4 was prepared by reaction of 4-[F-18] fluoromethylpiperidine with 4-(alpha-bromoacetyl)-4'-(4-methylpiperidinyl acetyl)biphenyl followed by reduction of the keto groups to alcohols with: NaBH4. The total synthesis time was 300 minutes and [18F]FA-4 was Obtained with a specific activity of 5.6 GBq/mu mol (EOS) and an overall decay corrected radiochemical yield of 3.1+/-0.6%. [C-11]pipzA-4 was prepared by reaction of [C-11]methyl triflate with 4-[1 -hydroxy-2-piperazinyl)ethyl]-4'-[1-hydroxy-2-(4-methylpiperidinyl)ethyl]- biphenyl. The total synthesis time was 25 minutes and [C-11]pipzA-4 was obtained with:a specific activity of 13.7 GBq/mu mol (EOS) and an overall decay corrected radiochemical yield of 19.5+/-2.2%.