2-氨基-1-(4-苄基-1-哌嗪基)-1-乙酮盐酸盐 | 1220018-02-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-氨基-1-(4-苄基-1-哌嗪基)-1-乙酮盐酸盐
• 英文名称: 2-amino-1-(4-benzylpiperazin-1-yl)ethanone dihydrochloride
• 英文别名: 2-Amino-1-(4-benzyl-1-piperazinyl)-1-ethanone hydrochloride；2-amino-1-(4-benzylpiperazin-1-yl)ethanone;hydrochloride
• CAS: 1220018-02-9
• 化学式: C₁₃H₁₉N₃O*2ClH
• 分子量: 306.235
• InChiKey: DQEGNXONLSFMLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  2-氨基-1-(4-苄基-1-哌嗪基)-1-乙酮盐酸盐 在 2,6-二氟吡啶 、 三氟甲磺酸酐 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 45.0h， 生成 3-(4-benzylpiperazin-1-yl)-7-phenylimidazo[1,2-a]pyrimidine
  参考文献：
  名称：

  三氟甲磺酸酐区域选择性合成3-氨基咪唑并[1,2-a]嘧啶

  摘要：

  摘要 据报道，通过三氟甲磺酸酐介导的酰胺活化和分子内环化的3-氨基咪唑并[1,2- a ]嘧啶的区域选择性合成。添加的吡啶碱的性质允许从简单的普通前体获得两种区域异构体。该方法容许一定范围的官能团，并提供对新型杂环支架的访问。 据报道，通过三氟甲磺酸酐介导的酰胺活化和分子内环化的3-氨基咪唑并[1,2- a ]嘧啶的区域选择性合成。添加的吡啶碱的性质允许从简单的普通前体获得两种区域异构体。该方法容许一定范围的官能团，并提供对新型杂环支架的访问。

  DOI：

  10.1055/s-0036-1588425
• 作为产物：
  描述：

  4-苄基-1-(Boc-氨基乙酰基)-哌嗪 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 2-氨基-1-(4-苄基-1-哌嗪基)-1-乙酮盐酸盐
  参考文献：
  名称：

  1,3-Dialkyl-substituted tetrahydropyrimido[1,2-f]purine-2,4-diones as multiple target drugs for the potential treatment of neurodegenerative diseases

  摘要：

  Adenosine receptors and monoamine oxidases are drug targets for neurodegenerative diseases such as Parkinson's and Alzheimer's disease. In the present study we prepared a library of 55 mostly novel tetrahydropyrimido[2,1-f]purinediones with various substituents in the 1- and 3-position (1,3-dimethyl, 1,3-diethyl, 1,3-dipropyl, 1-methyl-3-propargyl) and broad variation in the 9-position. A synthetic strategy to obtain 3-propargyl-substituted tetrahydropyrimido[2,1-f]purinedione derivatives was developed. The new compounds were evaluated for their interaction with all four adenosine receptor subtypes and for their ability to inhibit monoamine oxidases (MAO). Introduction of mono-or di-chloro-substituted phenyl, benzyl or phenethyl residues at N9 of the 1,3-dimethyl series led to the discovery of a novel class of potent MAO-B inhibitors, the most potent compound being 9-(3,4-dichlorobenzyl)-1,3-dimethyl-6,7,8,9-tetrahydropyrimido[1,2-f]purine-2,4(1H,3H)-dione (21g, IC50 human MAO-B: 0.0629 mu M), which displayed high selectivity versus the other investigated targets. Potent dually active A(1)/A(2A) adenosine receptor antagonists were identified, for example, 9-benzyl-1-methyl-3-propargyl-6,7,8,9-tetrahydropyrimido[1,2-f]purine-2,4(1H,3H)dione (19f, K-i, human receptors, A(1): 0.249 mu M, A(2A): 0.253 mu M). Several compounds showed triple-target inhibition, the best compound being 9-(2-methoxybenzyl)-1-methyl-3-(prop-2-ynyl)-6,7,8,9-tetrahydro pyrimido [1,2-f]purine-2,4(1H,3H)-dione (19g, K-i A(1): 0.605 mu M, K-i A(2A): 0.417 mu M, IC50 MAO-B: 1.80 mu M). Compounds inhibiting several different targets involved in neurodegeneration may exhibit additive or even synergistic effects in vivo. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.044

文献信息

• Regioselective Synthesis of 3-Aminoimidazo[1,2-a]pyrimidines with Triflic Anhydride
  作者：Eric Talbot、Robert Law、Sabri Ukuser、Daniel Tape

  DOI：10.1055/s-0036-1588425

  日期：2017.8

  regioselective synthesis of 3-aminoimidazo[1,2-a]pyrimidines via triflic anhydride mediated amide activation and intramolecular cyclisation is reported. The nature of the added pyridine base allows access to both regioisomers from a simple common precursor. The method tolerates a range of functional groups and provides access to novel heterocyclic scaffolds. The regioselective synthesis of 3-aminoimidazo[1

  摘要 据报道，通过三氟甲磺酸酐介导的酰胺活化和分子内环化的3-氨基咪唑并[1,2- a ]嘧啶的区域选择性合成。添加的吡啶碱的性质允许从简单的普通前体获得两种区域异构体。该方法容许一定范围的官能团，并提供对新型杂环支架的访问。 据报道，通过三氟甲磺酸酐介导的酰胺活化和分子内环化的3-氨基咪唑并[1,2- a ]嘧啶的区域选择性合成。添加的吡啶碱的性质允许从简单的普通前体获得两种区域异构体。该方法容许一定范围的官能团，并提供对新型杂环支架的访问。
• 1,3-Dialkyl-substituted tetrahydropyrimido[1,2-f]purine-2,4-diones as multiple target drugs for the potential treatment of neurodegenerative diseases
  作者：Pierre Koch、Rhalid Akkari、Andreas Brunschweiger、Thomas Borrmann、Miriam Schlenk、Petra Küppers、Meryem Köse、Hamid Radjainia、Jörg Hockemeyer、Anna Drabczyńska、Katarzyna Kieć-Kononowicz、Christa E. Müller

  DOI：10.1016/j.bmc.2013.09.044

  日期：2013.12

  Adenosine receptors and monoamine oxidases are drug targets for neurodegenerative diseases such as Parkinson's and Alzheimer's disease. In the present study we prepared a library of 55 mostly novel tetrahydropyrimido[2,1-f]purinediones with various substituents in the 1- and 3-position (1,3-dimethyl, 1,3-diethyl, 1,3-dipropyl, 1-methyl-3-propargyl) and broad variation in the 9-position. A synthetic strategy to obtain 3-propargyl-substituted tetrahydropyrimido[2,1-f]purinedione derivatives was developed. The new compounds were evaluated for their interaction with all four adenosine receptor subtypes and for their ability to inhibit monoamine oxidases (MAO). Introduction of mono-or di-chloro-substituted phenyl, benzyl or phenethyl residues at N9 of the 1,3-dimethyl series led to the discovery of a novel class of potent MAO-B inhibitors, the most potent compound being 9-(3,4-dichlorobenzyl)-1,3-dimethyl-6,7,8,9-tetrahydropyrimido[1,2-f]purine-2,4(1H,3H)-dione (21g, IC50 human MAO-B: 0.0629 mu M), which displayed high selectivity versus the other investigated targets. Potent dually active A(1)/A(2A) adenosine receptor antagonists were identified, for example, 9-benzyl-1-methyl-3-propargyl-6,7,8,9-tetrahydropyrimido[1,2-f]purine-2,4(1H,3H)dione (19f, K-i, human receptors, A(1): 0.249 mu M, A(2A): 0.253 mu M). Several compounds showed triple-target inhibition, the best compound being 9-(2-methoxybenzyl)-1-methyl-3-(prop-2-ynyl)-6,7,8,9-tetrahydro pyrimido [1,2-f]purine-2,4(1H,3H)-dione (19g, K-i A(1): 0.605 mu M, K-i A(2A): 0.417 mu M, IC50 MAO-B: 1.80 mu M). Compounds inhibiting several different targets involved in neurodegeneration may exhibit additive or even synergistic effects in vivo. (C) 2013 Elsevier Ltd. All rights reserved.