1-(4-pentyn-1-yl)pyrrolidine | 14044-58-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-(4-pentyn-1-yl)pyrrolidine
• 英文别名: 1-(pent-4-yn-1-yl)pyrrolidine；N-Pent-4-inyl-pyrrolidin；N-pent-4-ynylpyrrolidine；1-pent-4-ynylpyrrolidine
• CAS: 14044-58-7
• 化学式: C₉H₁₅N
• 分子量: 137.225
• InChiKey: SCSMBLBDVCTRLK-UHFFFAOYSA-N

物化性质

• 沸点：
  45 °C
• 密度：
  0.910±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-pentyn-1-yl)pyrrolidine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Gold-catalyzed efficient synthesis of azepan-4-ones via a two-step [5 + 2] annulation

  摘要：

  通过两步[5â+â2]环化反应合成氮杂环庚-4-酮的效率令人惊讶。该反应涉及一个关键的金催化反应，并显示出普遍较高的区域选择性和良好甚至极佳的非对映选择性。

  DOI：

  10.1039/c001314e
• 作为产物：
  描述：

  四氢吡咯 、 戊-4-炔基对甲苯磺酸酯 在 potassium carbonate 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以88%的产率得到1-(4-pentyn-1-yl)pyrrolidine
  参考文献：
  名称：

  Gold-catalyzed efficient synthesis of azepan-4-ones via a two-step [5 + 2] annulation

  摘要：

  通过两步[5â+â2]环化反应合成氮杂环庚-4-酮的效率令人惊讶。该反应涉及一个关键的金催化反应，并显示出普遍较高的区域选择性和良好甚至极佳的非对映选择性。

  DOI：

  10.1039/c001314e

文献信息

• 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。
• [EN] TRIARYLPYRIDINE COMPOUNDS AND USE THEREOF FOR TREATING CANCER<br/>[FR] COMPOSÉS DE TRIARYLPYRIDINE ET LEUR UTILISATION DANS LE CADRE DU TRAITEMENT DU CANCER
  申请人：INST NAT SANTE RECH MED

  公开号：WO2021239976A1

  公开（公告）日：2021-12-02

  The invention relates to new bis-triazole 2,4,6-triarylpyridines compounds and their use in the field of oncology, in particular in the prevention and/or treatment of cancer disease. The inventors have observed that the new bis-triazole 2,4,6-triarylpyridines were able to induce cancer cells death either as a standalone or, synergistically, in combination with a lysosomotropic agent, such as chloroquine. The compounds were active against a variety of cancer cells such as HeLa (cervical cancer cell), A549 (lung carcinoma), and PDX-2 or PDX-3 (lung adenocarcinoma). The invention also relates to compositions and methods for prevention and/or treatment of cancer diseases using the new bis-triazole 2,4,6-triarylpyridines compounds.

  该发明涉及新的双三唑基2,4,6-三芳基吡啶化合物及其在肿瘤学领域的应用，特别是在预防和/或治疗癌症疾病方面。发明人发现，新的双三唑基2,4,6-三芳基吡啶能够单独或与溶酶体靶向药物（如氯喹）联合，协同诱导癌细胞死亡。这些化合物对多种癌细胞具有活性，如HeLa（宫颈癌细胞）、A549（肺癌）和PDX-2或PDX-3（肺腺癌）。该发明还涉及使用新的双三唑基2,4,6-三芳基吡啶化合物预防和/或治疗癌症疾病的组合物和方法。
• NOVEL COMPOUNDS
  申请人：GlaxoSmithKline LLC

  公开号：US20140056928A1

  公开（公告）日：2014-02-27

  Compounds of formula (I) and salts thereof: wherein R 1 is n-C 1-6 alkyl or C 1-2 alkoxyC 1-2 alkyl-, R 2 is halo, OH or C 1-3 alkyl, m is an integer having a value of 4, 5, 6 or 7, n is an integer having a value of 0, 1, 2 or 3, and p is an integer having a value of 0, 1 or 2, are inducers of human interferon. Compounds which induce human interferon may be useful in the treatment of various disorders, for example the treatment of allergic diseases and other inflammatory conditions, for example allergic rhinitis and asthma, infectious diseases and cancer, and may also be useful as vaccine adjuvants.

  式（I）的化合物及其盐：其中R1是n-C1-6烷基或C1-2烷氧基C1-2烷基，R2是卤素、羟基或C1-3烷基，m是取值为4、5、6或7的整数，n是取值为0、1、2或3的整数，p是取值为0、1或2的整数，是人类干扰素的诱导剂。诱导人类干扰素的化合物可能在治疗各种疾病方面有用，例如治疗过敏性疾病和其他炎症性疾病，例如过敏性鼻炎和哮喘、传染病和癌症，也可能作为疫苗佐剂有用。
• 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。
• PYRAZOLOPYRIMIDINE COMPOUNDS
  申请人：GlaxoSmithKline LLC

  公开号：US20150225403A1

  公开（公告）日：2015-08-13

  Compounds of formula (I) and salts thereof: wherein R 1 is n-C 1-6 alkyl or C 1-2 alkoxyC 1-2 alkyl-, R 2 is halo, OH or C 1-3 alkyl, m is an integer having a value of 4, 5, 6 or 7, n is an integer having a value of 0, 1, 2 or 3, and p is an integer having a value of 0, 1 or 2, are inducers of human interferon. Compounds which induce human interferon may be useful in the treatment of various disorders, for example the treatment of allergic diseases and other inflammatory conditions, for example allergic rhinitis and asthma, infectious diseases and cancer, and may also be useful as vaccine adjuvants.

  化学式为（I）的化合物及其盐：其中R1为n-C1-6烷基或C1-2烷氧基C1-2烷基，R2为卤素、羟基或C1-3烷基，m为4、5、6或7的整数，n为0、1、2或3的整数，p为0、1或2的整数，是人干扰素的诱导剂。诱导人干扰素的化合物可能在治疗各种疾病方面有用，例如治疗过敏性疾病和其他炎症性疾病，例如过敏性鼻炎和哮喘，感染性疾病和癌症，并且可能还有用作疫苗佐剂。