N1-tritylspermidine | 334513-03-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N1-tritylspermidine
• 英文别名: N'-[3-(tritylamino)propyl]butane-1,4-diamine
• CAS: 334513-03-0
• 化学式: C₂₆H₃₃N₃
• 分子量: 387.568
• InChiKey: YGMZMQBGEOEZET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  50.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N1-tritylspermidine 在 盐酸 、 水 、 potassium carbonate 、 苯甲醚 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 2-amino-6-(3-(4-((3-aminopropyl)amino) butyl)ureido)-4-(piperidin-1-yl)pyrimidine 1-oxide bis-hydrochloride 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-[4-(trifluoroacetamido)butyl]-N-[3-(trifluoroacetamido)propyl]amine 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 N1-tritylspermidine
  参考文献：
  名称：

  Simple syntheses of cyclic polyamines using selectively N-tritylated polyamines and succinic anhydride

  摘要：

  Treatment of selectively N-tritylated spermidine and spermine derivatives with succinic anhydride, followed by PyBrOP-mediated intramolecular amide bond formation and LiAlH4 reduction, allows for an easy and general entry to cyclic polyamine derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00335-0

文献信息

• Synthesis and antioxidative/anti-inflammatory activity of novel fullerene–polyamine conjugates
  作者：George E. Magoulas、Thomas Garnelis、Constantinos M. Athanassopoulos、Dionissios Papaioannou、George Mattheolabakis、Konstantinos Avgoustakis、Dimitra Hadjipavlou-Litina

  DOI：10.1016/j.tet.2012.06.066

  日期：2012.9

  (E)-4-(Fullerenopyrrolidin-1-yl)-3-methylbut-2-enoic acid and its corresponding succinimidyl ester, readily obtained through Prato-type modification of C-60, were used for the selective N-acylation of polyamines. The thus obtained conjugates were evaluated for their antioxidative and anti-inflammatory activity and their cytotoxicity was determined. Members of this family of compounds showed interesting anti-lipid peroxidation, anti-lipoxygenase and anti-inflammatory activity and comparable cytocompatibility to spermidine. (C) 2012 Elsevier Ltd. All rights reserved.

  （E）-4-（富勒烯吡咯基）-3-甲基丁二烯酸和对应的丙二酸 succeedinimidyl 酯通过普拉托型修饰C-60易得，被广泛应用于富选择性N-酰化反应。由此获得的共轭体被评估为抗氧化及抗炎活性，同时测定它们的细胞毒性。本系列化合物显示出令人感兴趣的抗脂过氧化、抗氧酶活性及抗炎活性，且与苏丹类物质相比具有相近的细胞相容性。（C）2012 Elsevier Ltd. All rights reserved.
• Simple syntheses of N-alkylated spermidine fragments and analogues of the spermine alkaloid kukoamine A
  作者：Stratos Vassis、George Karigiannis、George Balayiannis、Maria Militsopoulou、Petros Mamos、George W Francis、Dionissios Papaioannou

  DOI：10.1016/s0040-4039(00)02308-x

  日期：2001.2

  trimethylsilyl γ-aminobutyrate and of N-trityl-γ-aminobutyric acid with methyl β-alaninate, respectively, followed by LiAlH4 reduction, produced N-monoalkylated spermidine fragments and analogues of the spermine alkaloid kukoamine A. The applicability of this methodology on the solid phase was also demonstrated.

  通过琥珀酰亚胺基N-三苯甲基-β-丙氨酸酯与三甲基甲硅烷基γ-氨基丁酸酯的偶合可容易地将琥珀酰胺化N-三苯甲基-β-丙氨酰基-γ-氨基丁酸酯和N-三苯甲基-γ-氨基丁酰基-β-丙氨酸酰化各种胺用N-三苯甲基-γ-氨基丁酸和β-丙氨酸甲酯分别还原，然后用LiAlH 4还原，生成N-单烷基化亚精胺片段和精胺生物碱kukoamine A的类似物。该方法在固相上的适用性也是演示。
• Simple syntheses of cyclic polyamines using selectively N-tritylated polyamines and succinic anhydride
  作者：Maria Militsopoulou、Nikolaos Tsiakopoulos、Christos Chochos、George Magoulas、Dionissios Papaioannou

  DOI：10.1016/s0040-4039(02)00335-0

  日期：2002.4

  Treatment of selectively N-tritylated spermidine and spermine derivatives with succinic anhydride, followed by PyBrOP-mediated intramolecular amide bond formation and LiAlH4 reduction, allows for an easy and general entry to cyclic polyamine derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis and evaluation of the antioxidative potential of minoxidil–polyamine conjugates
  作者：Dimitra Hadjipavlou-Litina、George E. Magoulas、Stavros E. Bariamis、Zinovia Tsimali、Konstantinos Avgoustakis、Christos A. Kontogiorgis、Constantinos M. Athanassopoulos、Dionissios Papaioannou

  DOI：10.1016/j.biochi.2013.03.009

  日期：2013.7

  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.