Trt-βAla-OSu | 58995-27-0

• 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: Trt-βAla-OSu
• 英文别名: Trt-β-Ala-OSu；2,5-Pyrrolidinedione, 1-[1-oxo-3-[(triphenylmethyl)amino]propoxy]-；(2,5-dioxopyrrolidin-1-yl) 3-(tritylamino)propanoate
• CAS: 58995-27-0
• 化学式: C₂₆H₂₄N₂O₄
• 分子量: 428.488
• InChiKey: HGGVNPIXXIFYOO-UHFFFAOYSA-N

物化性质

• 沸点：
  568.3±52.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Trt-βAla-OSu 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 N1-tritylspermidine
  参考文献：
  名称：

  Synthesis and antioxidative/anti-inflammatory activity of novel fullerene–polyamine conjugates

  摘要：

  （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.

  DOI：

  10.1016/j.tet.2012.06.066
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 N-trityl-β-alanine 在 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 20.0h， 生成 Trt-βAla-OSu
  参考文献：
  名称：

  Martelli, S., Farmaco, Edizione Scientifica, 1986, vol. 41, # 11, p. 881 - 891

  摘要：

  DOI：

文献信息

• 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 fragment syntheses of all four isomers of the spermine alkaloid kukoamine
  作者：George Karigiannis、Petros Mamos、George Balayiannis、Ioannis Katsoulis、Dionissios Papaioannou

  DOI：10.1016/s0040-4039(98)00940-x

  日期：1998.7

  All four isomers of the spermine alkaloid kukoamine were unambiguously prepared through diacylation with O,O′-dibenzylcaffeyl chloride of suitably protected (benzyl and/or trityl groups) spermine derivatives, assembled on solid and/or in liquid phase using β-alanine and γ-aminobutyric acid, followed by simultaneous N- and O- deprotection and double bond reduction using catalytic hydrogenation.

  通过与适当保护的（苄基和/或三苯甲基）精胺的O， O'-二苄基咖啡酰氯二酰化，明确制备精胺生物碱古柯胺的所有四个异构体，并使用β-丙氨酸和γ将其固相和/或液相组装-氨基丁酸，然后同时进行N-和O-脱保护和使用催化氢化的双键还原。
• 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 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.
• 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.