1-methyl-4-(pent-4-yn-1-yl)piperazine | 388121-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-methyl-4-(pent-4-yn-1-yl)piperazine
• 英文别名: 1-Methyl-4-(pent-4-ynyl)piperazine；1-methyl-4-pent-4-ynylpiperazine
• CAS: 388121-84-4
• 化学式: C₁₀H₁₈N₂
• 分子量: 166.266
• InChiKey: IRQWLKGRKSVZDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-4-(pent-4-yn-1-yl)piperazine 、 N-[3-(3-bromo-pyrazolo[1,5-a]pyrimidin-7-yl)-phenyl]-3-trifluoromethyl-benzamide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 3.0h， 以25%的产率得到N-(3-{3-[5-(4-methylpiperazin-1-yl)pent-1-yn-1-yl]pyrazolo[1,5-a]pyrimidin-7-yl}phenyl)-3-(trifluoromethyl)benzamide
  参考文献：
  名称：

  Non-hinge-binding pyrazolo[1,5-a]pyrimidines as potent B-Raf kinase inhibitors

  摘要：

  As part of our research effort to discover B-Raf kinase inhibitors, we prepared a series of C-3 substituted N-(3-(pyrazolo[1,5-a]pyrimidin-7-yl)phenyl)-3-(trifluoromethyl)benzamides. X-ray crystallography studies revealed that one of the more potent inhibitors (10n) bound to B-Raf kinase without forming a hinge-binding hydrogen bond. With basicamine residues appended to C-3 aryl residues, cellular activity and solubility were enhanced over previously described compounds of this class. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.049
• 作为产物：
  描述：

  N-甲基哌嗪 、 pent-4-yn-1-yl methanesulfonate 以 1,2-二氯乙烷 为溶剂， 反应 22.5h， 生成 1-methyl-4-(pent-4-yn-1-yl)piperazine
  参考文献：
  名称：

  ALKYNYL PYRROLOPYRIMIDINES AND RELATED ANALOGS AS HSP90-INHIBITORS

  摘要：

  炔基吡咯并[2,3-d]嘧啶及相关类似物被描述并证明具有作为热休克蛋白90（HSP90）抑制剂的效用，用于治疗和预防各种HSP90介导的疾病。还描述和声明了这类化合物的合成和使用方法。

  公开号：

  US20060223797A1

文献信息

• Pyrroloquinolones as antiviral agents
  申请人：——

  公开号：US20020055636A1

  公开（公告）日：2002-05-09

  The present invention provides a compound of formula I 1 which is useful as antiviral agents, in particular, as agents against viruses of the herpes family.

  本发明提供了一种化合物，其化学式为I，可用作抗病毒剂，特别是用于抗击疱疹病毒家族的药剂。
• Triarylpyridine Compounds and Chloroquine Act in Concert to Trigger Lysosomal Membrane Permeabilization and Cell Death in Cancer Cells
  作者：Jennifer Beauvarlet、Rabindra Nath Das、Karla Alvarez-Valadez、Isabelle Martins、Alexandra Muller、Elodie Darbo、Elodie Richard、Pierre Soubeyran、Guido Kroemer、Jean Guillon、Jean-Louis Mergny、Mojgan Djavaheri-Mergny

  DOI：10.3390/cancers12061621

  日期：——

  Lysosomes play a key role in regulating cell death in response to cancer therapies, yet little is known on the possible role of lysosomes in the therapeutic efficacy of G-quadruplex DNA ligands (G4L) in cancer cells. Here, we investigate the relationship between the modulation of lysosomal membrane damage and the degree to which cancer cells respond to the cytotoxic effects of G-quadruplex ligands belonging to the triarylpyridine family. Our results reveal that the lead compound of this family, 20A promotes the enlargement of the lysosome compartment as well as the induction of lysosome-relevant mRNAs. Interestingly, the combination of 20A and chloroquine (an inhibitor of lysosomal functions) led to a significant induction of lysosomal membrane permeabilization coupled to massive cell death. Similar effects were observed when chloroquine was added to three new triarylpyridine derivatives. Our findings thus uncover the lysosomal effects of triarylpyridines compounds and delineate a rationale for combining these compounds with chloroquine to increase their anticancer effects.

  溶酶体在调节细胞对癌症治疗的死亡起着关键作用，然而对溶酶体在G-四链体DNA连接物（G4L）对癌细胞的治疗效果中可能发挥的作用知之甚少。在这里，我们研究了溶酶体膜损伤的调节与癌细胞对属于三芳基吡啶家族的G-四链体配体的细胞毒效应之间的关系。我们的结果显示，该家族的主要化合物20A促进了溶酶体区的扩大以及溶酶体相关mRNA的诱导。有趣的是，20A与氯喹（一种溶酶体功能抑制剂）的组合导致了溶酶体膜通透性的显著诱导，伴随着大规模的细胞死亡。当氯喹添加到三种新的三芳基吡啶衍生物中时，也观察到了类似的效应。因此，我们的发现揭示了三芳基吡啶化合物的溶酶体效应，并勾勒出了将这些化合物与氯喹结合以增强其抗癌效果的合理性。
• Synthesis and Characterization of Bis-Triazolyl-Pyridine Derivatives as Noncanonical DNA-Interacting Compounds
  作者：Anna Di Porzio、Ubaldina Galli、Jussara Amato、Pasquale Zizza、Sara Iachettini、Nunzia Iaccarino、Simona Marzano、Federica Santoro、Diego Brancaccio、Alfonso Carotenuto、Stefano De Tito、Annamaria Biroccio、Bruno Pagano、Gian Cesare Tron、Antonio Randazzo

  DOI：10.3390/ijms222111959

  日期：——

  and/or iM DNAs and to affect the thermal stability of these structures. All the compounds were then clustered through multivariate data analysis, based on such capability. The most promising compounds were subjected to a further biophysical and biological characterization, leading to the identification of two molecules simultaneously able to stabilize G4s and destabilize iMs, both in vitro and in living

  除了众所周知的双螺旋构象外，DNA还能够折叠成各种非规范排列，例如G-四链体（G4s）和i-基序（iMs），它们在基因启动子、复制起点和端粒中的出现突出了DNA的广度他们可能调节的生物过程。特别是，先前的研究报道G4和iM结构可能在控制基因转录中发挥不同的作用。无论如何，仍然需要能够同时稳定/不稳定这些结构的分子工具来阐明生物学水平上发生的情况。在此，将多组分反应和点击化学功能化相结合，生成一组 31 个双三唑基吡啶衍生物，这些衍生物最初通过圆二色性筛选，以确定它们与不同 G4 和/或 iM DNA 相互作用的能力以及影响热稳定性的能力这些结构。然后，基于这种能力，通过多变量数据分析对所有化合物进行聚类。最有前途的化合物经过进一步的生物物理和生物学表征，从而鉴定出两种能够在体外和活细胞中同时稳定 G4 和不稳定 iM 的分子。
• [EN] PYRROLOQUINOLONES AS ANTIVIRAL AGENTS<br/>[FR] PYRROLOQUINOLONES EN TANT QU'AGENTS ANTIVIRAUX
  申请人：UPJOHN CO

  公开号：WO2002002558A1

  公开（公告）日：2002-01-10

  The present invention provides a compound of formula (I) which is useful as antiviral agents, in particular, as agents against viruses of the herpes family.

  本发明提供了一种化合物，其化学式为（I），该化合物可用作抗病毒剂，特别是用于对抗疱疹病毒家族的病毒。
• ALKYNYL PYRROLO[2,3-d]PYRIMIDINES AND RELATED ANALOGS AS HSP90-INHIBITORS
  申请人：Kasibhatla Srinivas Rao

  公开号：US20090318387A1

  公开（公告）日：2009-12-24

  Alkynyl pyrrolo[2,3-d]pyrimidines and related analogs are described and demonstrated to have utility as Heat Shock Protein 90 (HSP90) inhibiting agents used in the treatment and prevention of various HSP90 mediated disorders. Methods of synthesis and use of such compounds are also described and claimed.

  本文描述了炔基吡咯并[2,3-d]嘧啶及其相关类似物，证明其作为热休克蛋白90（HSP90）抑制剂在治疗和预防各种HSP90介导的疾病中具有用途。同时还描述和声明了这些化合物的合成和使用方法。