5-amino-7-(piperidin-1-yl)-2H-[1,2,4]oxadiazolo[2,3-c]pyrimidin-2-one | 122185-20-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-amino-7-(piperidin-1-yl)-2H-[1,2,4]oxadiazolo[2,3-c]pyrimidin-2-one
• 英文别名: 5-Amino-7-piperidin-1-yl-[1,2,4]oxadiazolo[2,3-c]pyrimidin-2-one
• CAS: 122185-20-0
• 化学式: C₁₀H₁₃N₅O₂
• 分子量: 235.246
• InChiKey: DTHRTNXFSCFNOM-UHFFFAOYSA-N

物化性质

• 熔点：
  225-227 °C (decomp)(Solvent: Acetonitrile)
• 沸点：
  367.7±45.0 °C(predicted)
• 密度：
  1.68±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-amino-7-(piperidin-1-yl)-2H-[1,2,4]oxadiazolo[2,3-c]pyrimidin-2-one 在 苯甲醚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-amino-6-(3-(4-((3-aminopropyl)amino) butyl)ureido)-4-(piperidin-1-yl)pyrimidine 1-oxide trifluoroacetate salt
  参考文献：
  名称：

  Synthesis and evaluation of the antioxidative potential of minoxidil–polyamine conjugates

  摘要：

  A series of conjugates (MNX-CO-PA) of minoxidil (MNX) with the polyamines (PAs) putrescine (PUT), spermidine (SPD) and spermine (SPM) as well as dopamine were produced through activation of MNX with N,N'-carbonyldiimidazole, followed by reaction with dopamine or selectively protected PAs and acid-mediated deprotection. These conjugates together with conjugates of the general type MNX-PA or PA-MNX-PA, readily produced using literature protocols, were tested as antioxidants. The most potent inhibitors of lipid peroxidation were the conjugates MNX SPM (2, 94%), SPM-MNX-SPM (4, 94%) and MNX-N-4-SPD (7, 91%) and MNX (91%). The most powerful lipoxygenase (LOX) inhibitors were MNX (IC50 = 20 mu M) and the conjugates MNX N-8-SPD (9, IC50 = 22.1 mu M), MNX-CO dopamine (11, IC50 = 28 mu M) and MNX-N-1-SPD (8, IC50 = 30 mu M). The most interesting conjugates 2, MNX-CO-PUT (5), 8 and 11 as well as MNX were generally found to exhibit weaker (22-36.5%) or no (conjugate 8) anti-inflammatory activity than indomethacin (47%) with the exception of MNX which showed almost equal potency (49%) to indomethacin. The cytocompatibility of conjugates and MNX at the highest concentration of 100 mu M showed a survival percentage of 87-107%, with the exception of conjugates with SPM (compound 2) and MNX-CO-SPM (6), which showed considerable cytotoxicity (survival percentage 8-14%). Molecular docking studies were carried on conjugate 9 and the parent compound MNX and were found to be in accordance with our experimental biological results. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biochi.2013.03.009
• 作为产物：
  描述：

  N,N'-羰基二咪唑 、 米诺地尔 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以60%的产率得到5-amino-7-(piperidin-1-yl)-2H-[1,2,4]oxadiazolo[2,3-c]pyrimidin-2-one
  参考文献：
  名称：

  Synthesis of minoxidil conjugates and their evaluation as HL-60 differentiation agents

  摘要：

  Activation of minoxidil (MNX) with N,N'-carbonyldiimidazole and coupling with natural polyamines (PAs) and commercially available aliphatic or aromatic amines provided a series of new conjugates which were evaluated for their ability to induce differentiation to HL-60 acute myeloid leukemia cancer cells, using a modified NBTZ reduction test. Although neither MNX nor 4,4'-methylenedianiline (MDA) or 2,7-diaminofluorene (DAF), alone or in combination, had any effect, the MNX-spermine (SPM) conjugate (11) and the conjugates 7 and 8 of MNX with MDA and DAF exhibited a differentiation-inducing effect at a concentration of 10 mu M without being toxic on proliferating human peripheral blood mononuclear cells. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.01.048

文献信息

• Synthesis of novel 6-piperidin-1-ylpyrimidine-2,4-diamine 3-oxide substituted calix[4]arene as a highly selective and sensitive fluorescent sensor for Cu2+ in aqueous samples
  作者：Ali Akbarzadeh、Reza Zadmard、Mohammad Reza Jalali

  DOI：10.1016/j.tetlet.2020.151658

  日期：2020.3

  In this study, we designed and synthesized a novel sensitive fluorescent sensor for Cu2+ cation by attaching two minoxidil molecules at the lower-rim of calix[4]arene annulus via the formation of two urea linkages. This chemosensor can selectively recognize Cu2+ in EtOH containing 5% H2O through a significant decline in fluorescence emission. The structure of the target molecule was determined by HRMS

  在这项研究中，我们通过形成两个脲键，将两个米诺地尔分子连接在杯[4]芳烃环的下边缘，从而设计并合成了一种新颖的Cu 2+阳离子灵敏荧光传感器。该化学传感器可以通过荧光发射的显着下降来选择性地识别含有5％H 2 O的EtOH中的Cu 2+。通过HRMS，1 H NMR，13 C NMR和FT-IR确定靶分子的结构。
• Synthetic studies toward the development of novel minoxidil analogs and conjugates with polyamines
  作者：George E. Magoulas、Stavros E. Bariamis、Constantinos M. Athanassopoulos、Dionissios Papaioannou

  DOI：10.1016/j.tetlet.2010.02.037

  日期：2010.4

  Syntheses of novel polyamine-modified minoxidil analogs (PMMs) and minoxidil-polyamine conjugates (MPCs) are described in an effort to improve the biological activity and selectivity of minoxidil and its poor solubility in water. (C) 2010 Elsevier Ltd. All rights reserved.