N1-Triphenylmethyl-1,4-diaminobutane | 189341-61-5

• 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-Triphenylmethyl-1,4-diaminobutane
• 英文别名: N'-tritylbutane-1,4-diamine
• CAS: 189341-61-5
• 化学式: C₂₃H₂₆N₂
• 分子量: 330.473
• InChiKey: HQKDFYFSZCDXNN-UHFFFAOYSA-N

物化性质

• 沸点：
  466.2±33.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2923900090

反应信息

• 作为反应物：
  描述：

  N1-Triphenylmethyl-1,4-diaminobutane 在 sodium hydroxide 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 6,10-Bis(mesitylenesulfonyl)-1-triphenylmethyl-1,6,10-triazatridecane
  参考文献：
  名称：

  A Comparison of Structure−Activity Relationships between Spermidine and Spermine Analogue Antineoplastics

  摘要：

  A systematic investigation of the impact of spermidine analogues both in vitro and in vivo is described. The study characterizes the effects of these analogues on L1210 cell growth, polyamine pools, ornithine decarboxylase, S-adenosyl-L-methionine decarboxylase, spermidine/spermine N-1-acetyltransferase, the maintenance of cellular charge, i.e., cationic equivalence associated with the polyamines and their analogues, and compares their ability to compete with spermidine for transport. The findings clearly demonstrate that the activity of-the linear polyamine analogues is highly dependent on the length of the triamines and the size of the N-alpha,N-omega-substituents. It appears that there is an optimum chain length for various activities and that the larger the N-alpha,N-omega-alkyls, the less active the compound. Metabolic transformation including N-dealkylation of these compounds is also evaluated. While there is no monotonic relationship between chain length and the ability of the analogue to be metabolized, the dipropyl triamines are clearly more actively catabolized than the corresponding methyl and ethyl systems. A comparison of the triamines with the corresponding tetraamines is made throughout the text regarding both in vitro activity against L1210 cells and in vivo toxicity measurements, suggesting that several triamine analogues may offer therapeutic advantages over the corresponding tetraamines.

  DOI：

  10.1021/jm960849j
• 作为产物：
  描述：

  在 哌啶 作用下， 以 甲醇 为溶剂， 以240 mg的产率得到N1-Triphenylmethyl-1,4-diaminobutane
  参考文献：
  名称：

  Triphenylbutanamines: Kinesin Spindle Protein Inhibitors with in Vivo Antitumor Activity

  摘要：

  The human mitotic kinesin Eg5 represents a novel mitotic spindle target for cancer chemotherapy. We previously identified S-trityl-L-cysteine (STLC) and related analogues as selective potent inhibitors of Eg5. We herein report on the development of a series of 4,4,4-triphenylbutan-1-amine inhibitors derived from the STLC scaffold. This new generation systematically improves on potency: the most potent C-trityl analogues exhibit K-i(aPP) <= 10 nM and GI(50) approximate to 50 nM, comparable to results from the phase II clinical benchmark ispinesib. Crystallographic studies reveal that they adopt the same overall binding configuration as S-trityl analogues at an allosteric site formed by loop L5 of Eg5. Evaluation of their druglike properties reveals favorable profiles for future development and, in the clinical candidate ispinesib, moderate hERG and CYP inhibition. One triphenylbutanamine analogue and ispinesib possess very good bioavailability (51% and 45%, respectively), with the former showing in vivo antitumor growth activity in nude mice xenograft studies.

  DOI：

  10.1021/jm201195m

文献信息

• FLUOROPHORE CHELATED LANTHANIDE LUMINESCENT PROBES WITH IMPROVED QUANTUM EFFICIENCY
  申请人：Mustaev Arkady

  公开号：US20130202536A1

  公开（公告）日：2013-08-08

  The invention relates to novel luminescent compositions of matter containing a fluorophore, synthetic methods for making the compositions, macromolecular conjugates of the compositions, and the use of the compositions in various methods of detection. The invention also provides kits containing the compositions and their conjugates for use in the methods of detection.

  这项发明涉及含有荧光物质的新型发光组合物，制备这些组合物的合成方法，这些组合物的高分子共轭物，以及在各种检测方法中使用这些组合物的用途。该发明还提供了包含这些组合物及其共轭物的试剂盒，用于上述检测方法。
• Azulene derivatives
  申请人：Boehringer Mannheim GmbH

  公开号：US06121322A1

  公开（公告）日：2000-09-19

  The invention provides novel azulene derivatives of general formula I ##STR1## wherein R.sub.1 to R.sub.6 have the significance given in the description, as well as their tautomers, enantiomers, diastereomers, racemates and physiologically compatible salts or esters and substances which are hydrolyzed or metabolized in vivo to compounds of formula I. The invention is also concerned with a process and intermediates for the manufacture of the above compounds, pharmaceutical compositions which contain such compounds as well as the use of these compounds in the treatment of inflammatory conditions.

  该发明提供了一种通式I的新型蓝紫烯衍生物##STR1##其中R.sub.1至R.sub.6在描述中给出的含义，以及它们的互变异构体、对映异构体、非对映异构体、消旋体和生理兼容性盐或酯，以及在体内水解或代谢为通式I化合物的物质。该发明还涉及制备上述化合物的过程和中间体，含有这些化合物的药物组合物，以及在治疗炎症性疾病中使用这些化合物。
• New Cross-Linking Quinoline and Quinolone Derivatives for Sensitive Fluorescent Labeling
  作者：Shyamala Pillai、Maxim Kozlov、Salvatore A. E. Marras、Lev N. Krasnoperov、Arkady Mustaev

  DOI：10.1007/s10895-012-1039-z

  日期：2012.7

  A variety of contemporary analytical platforms, utilized in technical and biological applications, take advantage of labeling the objects of interest with fluorescent tracers—compounds that can be easily and sensitively detected. Here we describe the synthesis of new fluorescent quinoline and quinolone compounds, whose light emission can be conveniently tuned by simple structural modifications. Some of these compounds can be used as sensitizers for lanthanide emission in design of highly sensitive luminescent probes. In addition, we also describe simple efficient derivatization reactions that allow introduction of amine- or click-reactive cross-linking groups into the fluorophores. The reactivity of synthesized compounds was confirmed in reactions with low molecular weight nucleophiles, or alkynes, as well as with click-reactive DNA-oligonucleotide containing synthetically introduced alkyne groups. These reactive derivatives can be used for covalent attachment of the fluorophores to various biomolecules of interest including nucleic acids, proteins, living cells and small cellular metabolites. Obtained compounds are characterized using NMR, steady-state fluorescence spectroscopy as well as UV absorption spectroscopy.

  多种现代分析平台，在技术和生物应用中，利用了用荧光示踪剂标记感兴趣物体的方法——这些化合物可以被轻松且敏感地检测到。在这里，我们描述了新型荧光喹啉和喹诺酮化合物的合成，其光发射可以通过简单的结构修饰方便地调节。其中一些化合物可用作镧系发射的敏化剂，用于设计高灵敏度发光探针。此外，我们还描述了简单的有效衍生化反应，允许将胺或点击反应性交联基团引入荧光团。合成化合物与低分子量亲核试剂或炔烃以及带有人工引入的炔基的点击反应性DNA-寡核苷酸的反应证实了其反应性。这些反应性衍生物可用于将荧光团共价结合到各种感兴趣的生物分子，包括核酸、蛋白质、活细胞和小细胞代谢物。所得化合物通过NMR、稳态荧光光谱学以及UV吸收光谱学进行表征。
• General Approach for the Liquid-Phase Fragment Synthesis of Orthogonally Protected Naturally Occurring Polyamines and Applications Thereof
  作者：Stefania Kalantzi、Constantinos M. Athanassopoulos、Raili Ruonala、Yrjo Helariutta、Dionissios Papaioannou

  DOI：10.1021/acs.joc.9b02066

  日期：2019.12.6

  Orthogonally protected polyamines (PAs) have been synthesized using α,ω-diamines and ω-aminoalcohols as N-Cx-N and N-Cy synthons, respectively, and the Mitsunobu reaction as the key reaction for the assembly of the PA skeleta. The Trt, Dde, and Phth groups have been employed for protecting the primary amino functions and the Ns group for activating the primary amino functions toward alkylation and

  已经使用 α,ω-二胺和 ω-氨基醇分别作为 N-Cx-N 和 N-Cy 合成子合成了正交保护的多胺 (PA)，并且 Mitsunobu 反应是 PA 骨架组装的关键反应。Trt、Dde 和 Phth 基团已用于保护伯氨基功能，Ns 基团用于激活伯氨基功能以实现烷基化和仲氨基功能保护。该方法很容易扩展以适应蜘蛛毒素 Agel 416 和 HO-416b 的全合成，分别包含 3-4-3-3 和 3-3-3-4 PA 骨架。
• New Analogs of Polyamine Toxins from Spiders and Wasps: Liquid Phase Fragment Synthesis and Evaluation of Antiproliferative Activity
  作者：Christos Vassileiou、Stefania Kalantzi、Eleanna Vachlioti、Constantinos M. Athanassopoulos、Christos Koutsakis、Zoi Piperigkou、Nikos Karamanos、Theodora Stivarou、Peggy Lymberi、Konstantinos Avgoustakis、Dionissios Papaioannou

  DOI：10.3390/molecules27020447

  日期：——

  MDA-MB-231 breast cancer cells, using Agel 416 and HO-416b as reference compounds. All five analogs of PhTX-433 were of very low activity on both cell lines, whereas the two analogs of JSTX-3 were highly active only on the MCF-7 cell line with IC50 values of 2.63–2.81 μΜ. Of the remaining three Agel 416 or HO-416b analogs, only the one with the spermidine chain was highly active on both cells with IC50 values

  多胺毒素 (PAT) 是多胺 (PA) 与亲脂性羧酸的结合物，最近已显示其具有抗增殖活性。合成了 10 种蜘蛛 PATs Agel 416、HO-416b 和 JSTX-3 和黄蜂 PAT PhTX-433 的类似物，改变了亲脂性头基和/或 PA 链，并在 MCF-7 上评估了它们的抗增殖活性和 MDA-MB-231 乳腺癌细胞，使用 Agel 416 和 HO-416b 作为参考化合物。PhTX-433 的所有五种类似物对两种细胞系的活性都非常低，而 JSTX-3 的两种类似物仅对 MCF-7 细胞系具有高活性，IC50 值为 2.63-2.81 μM。在其余三种 Agel 416 或 HO-416b 类似物中，只有一种带有亚精胺链的类似物对两种细胞都具有高活性，IC50 值为 3.15–12.6 μM。该系列中最有效的两种化合物 Agel 416 和 HO-416b 对两种细胞系的 IC50