N⁸,N⁸-dibenzyl-N¹-tritylspermidine | 334513-28-9

• 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: N⁸,N⁸-dibenzyl-N¹-tritylspermidine
• 英文别名: N',N'-dibenzyl-N-[3-(tritylamino)propyl]butane-1,4-diamine
• CAS: 334513-28-9
• 化学式: C₄₀H₄₅N₃
• 分子量: 567.817
• InChiKey: VGMJBJPTTLDBDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  43
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  27.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N⁸,N⁸-dibenzyl-N¹-tritylspermidine 在 palladium on activated charcoal 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 、 乙酸乙酯 为溶剂， 反应 31.25h， 生成 N1,N10-bis(dihydrocaffeoyl)spermidine
  参考文献：
  名称：

  N-烷基化亚精胺片段和精胺生物碱苦瓜胺A类似物的简单合成

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(00)02308-x
• 作为产物：
  描述：

  Trt-β-Ala-γ-Aba-OSu 在 lithium aluminium tetrahydride 、 氨 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 N⁸,N⁸-dibenzyl-N¹-tritylspermidine
  参考文献：
  名称：

  N-烷基化亚精胺片段和精胺生物碱苦瓜胺A类似物的简单合成

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(00)02308-x

文献信息

• Synthesis and antimicrobial activity of chloramphenicol–polyamine conjugates
  作者：George E. Magoulas、Ourania N. Kostopoulou、Thomas Garnelis、Constantinos M. Athanassopoulos、Georgia G. Kournoutou、Michael Leotsinidis、George P. Dinos、Dionissios Papaioannou、Dimitrios L. Kalpaxis

  DOI：10.1016/j.bmc.2015.04.069

  日期：2015.7

  A series of chloramphenicol (CAM) amides with polyamines (PAs), suitable for structure-activity relationship studies, were synthesized either by direct attachment of the PA chain on the 2-aminopropane- 1,3-diol backbone of CAM, previously oxidized selectively at its primary hydroxyl group, or from chloramphenicol base (CLB) through acylation with succinic or phthalic anhydride and finally coupling with a PA. Conjugates 4 and 5, in which the CLB moiety was attached on N4 and N1 positions, respectively, of the N-8,N-8-dibenzylated spermidine through the succinate linker, were the most potent antibacterial agents. Both conjugates were internalized into Escherichia coli cells by using the spermidine-preferential uptake system and caused decrease in protein and polyamine content of the cells. Noteworthy, conjugate 4 displayed comparable activity to CAM in MRSA or wild-type strains of Staphylococcus aureus and Escherichia coli, but superior activity in E. coli strains possessing ribosomal mutations or expressing the CAM acetyltransferase (cat) gene. Lead compounds, and in particular conjugate 4, have been therefore discovered during the course of the present work with clinical potential. (C) 2015 Elsevier Ltd. All rights reserved.
• Simple syntheses of the polyamine alkaloid tenuilobine and analogues using selectively N-tritylated polyamines and dicarboxylic acids as bridging elements
  作者：Stratos Vassis、Ioannis Govaris、Katerina Voyagi、Petros Mamos、Dionissios Papaioannou

  DOI：10.1016/s0040-4039(02)00338-6

  日期：2002.4

  Selectively N-tritylated spermidine and spermine derivatives and the monophenacyl ester of 1,16-hexadecanedioic acid (Hda) were used to obtain the polyamine alkaloid tenuilobine and its fully reduced analogue. Other symmetric or side-chain-shortened tenuilobine analogues were readily obtained by using Hda or its dichloride or succinic anhydride to bridge the polyamine moieties. (C) 2002 Elsevier Science 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。