N¹,N⁸-ditritylspermidine | 244033-13-4

• 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,N⁸-ditritylspermidine
• 英文别名: N'-trityl-N-[3-(tritylamino)propyl]butane-1,4-diamine
• CAS: 244033-13-4
• 化学式: C₄₅H₄₇N₃
• 分子量: 629.888
• InChiKey: BXWVXCXWIUCXHR-UHFFFAOYSA-N

物化性质

• 熔点：
  127-130 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  734.5±60.0 °C(Predicted)
• 密度：
  1.087±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  36.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N¹,N⁸-ditritylspermidine 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  带有多胺连接基的青蒿素二聚体的合成及其作为抗癌药的潜力评估

  摘要：

  天然产物青蒿素及其衍生物目前被认为是治疗疟疾的选择药物。同时，大量此类药物也显示出令人感兴趣的抗癌活性。在目前的研究工作中，青蒿素经过结构修饰并固定在天然多胺上，以提供新的青蒿素二聚体共轭物，并对其潜在的抗癌活性进行了评估。测试的所有青蒿素缀合物在减少MCF7乳腺癌细胞数量方面比青蒿素本身更有效。该作用需要结合，而不是由青蒿素类似物或多胺单独或组合引起。为了行动的阐发潜在机制，我们使用了最有效的结合物6，7，9和12，发现它们降低了癌细胞自身血管生成生长因子多效性蛋白的表达和分泌，并抑制了体内血管生成和体外内皮细胞的生长。这些数据表明，新的青蒿素二聚体是开发有效抗癌剂的良好候选者。

  DOI：

  10.1016/j.bmc.2017.05.018
• 作为产物：
  描述：

  N1-Triphenylmethyl-1,4-diaminobutane 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.5h， 生成 N¹,N⁸-ditritylspermidine
  参考文献：
  名称：

  Simple syntheses of the polyamine alkaloid tenuilobine and analogues using selectively N-tritylated polyamines and dicarboxylic acids as bridging elements

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(02)00338-6

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.
• Synthesis and Antiplasmodial Activity of Novel Fosmidomycin Derivatives and Conjugates with Artemisinin and Aminochloroquinoline
  作者：Despina Palla、Antonia I. Antoniou、Michel Baltas、Christophe Menendez、Philippe Grellier、Elisabeth Mouray、Constantinos M. Athanassopoulos

  DOI：10.3390/molecules25204858

  日期：——

  the development of drug resistance by Plasmodium falciparum. The antibiotic fosmidomycin (FSM) is also known for its antimalarial activity by targeting the non-mevalonate isoprenoid synthesis pathway, which is essential for the malaria parasites but is absent in mammalians. In this study, we synthesized and evaluated against the chloroquine-resistant P. falciparum FcB1/Colombia strain, a series of FSM

  尽管作出了许多努力，但疟疾仍然是全世界最成问题的传染病之一，主要是由于恶性疟原虫产生了耐药性。抗生素磷磷霉素（FSM）还具有靶向非甲羟戊酸类异戊二烯合成途径的抗疟疾活性，该途径对疟疾寄生虫至关重要，但在哺乳动物中却不存在。在这项研究中，我们合成并针对抗氯喹的恶性疟原虫FcB1 / Colombia菌株，一系列FSM类似物，衍生物和与其他抗疟疾药物（如青蒿素（ART）和氨基氯喹啉（ACQ））的缀合物进行了合成和评估。生物学评估发现，有四种新化合物具有比FSM更高的抗疟活性：两种FSM-ACQ衍生物和两种FSM-ART结合物，其有效活性是FSM的3.5-5.4和41.5-23.1倍，
• Efficient Syntheses of Polyamines Bearing 1<i>H</i>-Tetrazol-5-yl Units on Their Amino Functions
  作者：Constantinos Athanassopoulos、Thomas Garnelis、George Magoulas、Dionissios Papaioannou

  DOI：10.1055/s-2006-942502

  日期：——

  Linear N-benzyl-N′-trityl-α,ω-diamines and N α, N ω-ditritylpolyamines were efficiently converted into the corresponding N-(1-benzyltetrazol-5-yl)-substituted derivatives upon treatment with benzyl isothiocyanate followed by reaction of the thus-obtained thioureas with azidotrimethylsilane under Mitsunobu reaction conditions.

  用异硫氰酸苄酯处理线性 N-苄基-N′-三苯甲基-δ,Ï-二胺和 Nδ,NÏ-二苯甲基多胺后，在三忍反应条件下，将得到的硫脲类化合物与叠氮三甲基硅烷反应，可有效地转化为相应的 N-（1-苄基四唑-5-基）取代衍生物。
• 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.
• Synthesis of spermidine and norspermidine dimers as high affinity polyamine transport inhibitors
  作者：Laurence Covassin、Michel Desjardins、René Charest-Gaudreault、Marie Audette、Marie-Josée Bonneau、Richard Poulin

  DOI：10.1016/s0960-894x(99)00262-0

  日期：1999.6

  A series of novel spermidine and sym-norspermidine dimers was synthesized by crosslinking the polyamine backbones via alkylation of their secondary amino groups to butyl, trans-2-butenyl, 2-butynyl or p-xylyl bridges. The resulting hexamines behaved as high-affinity antagonists of polyamine uptake, with a relative potency that was dependent on the geometry of the linker structure. (C) 1999 Elsevier Science Ltd. All rights reserved.