4-氯-2,7-二甲基-1,8-二氮杂萘 | 84670-41-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 4-氯-2,7-二甲基-1,8-二氮杂萘
• 英文名称: 4-chloro-2,7-dimethyl-1,8-naphthyridine
• 英文别名: 4-Chloro-2,7-dimethyl-[1,8]naphthyridine
• CAS: 84670-41-7
• 化学式: C₁₀H₉ClN₂
• 分子量: 192.648
• InChiKey: LFUQUCOYQGAFFE-UHFFFAOYSA-N

物化性质

• 熔点：
  83 °C(Solv: ligroine (8032-32-4))
• 沸点：
  283.7±35.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氯-2,7-二甲基-1,8-二氮杂萘 在 4-二甲氨基吡啶 、 selenium(IV) oxide 、 palladium 10% on activated carbon 、 甲酸铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.0h， 生成 N,N'-di(quinolin-3-yl)-1,8-naphthyridine-2,7-dicarboxamide
  参考文献：
  名称：

  Selective G-quadruplex DNA Stabilizing Agents Based on Bisquinolinium and Bispyridinium Derivatives of 1,8-Naphthyridine

  摘要：

  Various biologically relevant G-quadruplex DNA structures offer a platform for therapeutic intervention for altering the gene expression or by halting the function of proteins associated with telomeres. One of the prominent strategies to explore the therapeutic potential of quadruplex DNA structures is by stabilizing them with small molecule ligands. Here we report the synthesis of bisquinolinium and bispyridinium derivatives of 1,8-naphthyridine and their interaction with human telomeric DNA and promoter G-quadruplex forming DNAs. The interactions of ligands with quadruplex forming DNAs were studied by various biophysical, biochemical, and computational methods. Results indicated that bisquinolinium ligands bind tightly and selectively to quadruplex DNAs at low ligand concentration (similar to 0.2-0.4 mu M). Furthermore, thermal melting studies revealed that ligands imparted higher stabilization for quadruplex DNA (an increase in the T-m of up to 21 degrees C for human telomeric G-quadruplex DNA and >25 degrees C for promoter G-quadruplex DNAs) than duplex DNA (Delta T-m < 1.6 degrees C). Molecular dynamics simulations revealed that the end-stacking binding mode was favored for ligands with low binding free energy. Taken together, the results indicate that the naphthyridine-based ligands with quinolinium and pyridinium side chains form a promising class of quadruplex DNA stabilizing agents having high selectivity for quadruplex DNA structures over duplex DNA structures.

  DOI：

  10.1021/jo201816g
• 作为产物：
  描述：

  2-氯甲基-6-甲基-4h-吡啶并[1,2-a]嘧啶-4-酮 在 三氯氧磷 作用下， 以 二苯醚 为溶剂， 反应 6.0h， 生成 4-氯-2,7-二甲基-1,8-二氮杂萘
  参考文献：
  名称：

  某些取代的吡啶并[1,2 - a ]嘧啶-4-酮和1,8-萘啶的合成

  摘要：

  通过将取代的2-氨基吡啶与δ-酮羧酸酯在PPA中缩合，得到取代的4 H-吡啶并[1，2 - a ]嘧啶-4-酮（I）。一些衍生物I被转化为相应的1、8-萘啶II和III。

  DOI：

  10.1002/jhet.5570200442

文献信息

• Simple and Efficient Synthesis of 2,7-Difunctionalized-1,8-Naphthyridines
  作者：S. Goswami、R. Mukherjee、R. Mukherjee、S. Jana、A. Maity、A. Adak

  DOI：10.3390/10080929

  日期：——

  The syntheses in good yields of some new difunctionalized 1,8-naphthyridines 4, 6, 8 and 9 and a novel triethylene glycol ether-linked dinaphthyridine, 10a, along with the mononaphthyridine-linked ether alcohol 10b are described. An improved and milder method for the synthesis of 2,7-diamino-1,8-naphthyridine (14) is also reported.

  描述了一些新的双官能化 1,8-萘啶 4、6、8 和 9 和新型三甘醇醚连接的二萘啶 10a 以及单萘啶连接的醚醇 10b 的高产率合成。还报道了一种用于合成 2,7-二氨基-1,8-萘啶 (14) 的改进和更温和的方法。
• Design and Synthesis of Multidentate Dinucleating Ligands Based on 1,8-Naphthyridine
  作者：Chuan He、Stephen J Lippard

  DOI：10.1016/s0040-4020(00)00748-1

  日期：2000.10

  Several novel multidentate dinucleating ligands based on 1,8-naphthyridine have been synthesized in which the 1,8-naphthyridine moiety serves as a bridging unit. These ligands can link two metal ions like the syn, syn coordination mode of bridging carboxylate groups encountered in a variety of dimetallic centers in biology. Stable dimetallic complexes with variable metal–metal separations and geometries

  已经合成了几种基于1，8-萘啶的新颖的多齿二核配体，其中1，8-萘啶部分用作桥连单元。这些配体可以连接两个金属离子，例如架桥在各种生物学上的双金属中心所遇到的羧酸根基团的syn，syn配位模式。使用这些配体可以轻松形成具有可变的金属-金属间距和几何形状的稳定双金属配合物。
• Practical Synthesis of 1,8-Naphthyridine-2,7-dialdehydes Syntone
  作者：I.I. Levina、A.A. Gridnev

  DOI：10.14233/ajchem.2019.22229

  日期：2019.10.12

  Several synthetic approaches for synthesizing 1,8-naphthyridines were tested. Reliable protocols for synthesis of some new 1,8-naphthyridine-2,7-dialdehydes were developed starting from 2-amino-6-methylpyridine and acetoacetate. The dialdehyde were found to react with pyrrole to form either a polymer or a macrocycle depending on conditions.

  测试了几种用于合成1,8-萘啶的合成方法。从2-氨基-6-甲基吡啶和乙酰乙酸酯开始，开发了一些新的1,8-萘啶-2,7-二醛的可靠合成方案。发现这些二醛与吡咯反应，根据条件可形成聚合物或大环化合物。
• Synthesis of bis(2-chloroethyl)amino-1,8-naphthyridines for evaluation as anticancer agents
  作者：Pier Luigi Ferrarini、Claudio Mori、Giuliana Biagi、Oreste Livi、Imperio Tonetti

  DOI：10.1002/jhet.5570210229

  日期：1984.3

  Some 1,8-naphthyridine nitrogen mustards have been synthesized for studies of their antitumor potentialities. All the tested intermediate and target compounds are devoid of antitumor properties.

  已经合成了一些1,8-萘啶氮芥，用于研究其抗肿瘤潜力。所有测试的中间体和目标化合物都没有抗肿瘤特性。
• Heteroaryl Substituted Quinolin-4-Ylamine Analogues
  申请人：Caldwell M. Timothy

  公开号：US20080085901A1

  公开（公告）日：2008-04-10

  Heteroaryl substituted quinolin-4-ylamine analogues of Formula I are provided. Such compounds are ligands that may be used to modulate specific receptor activity in vivo or in vitro, and are particularly useful in the treatment of conditions associated with pathological receptor activation in humans, domesticated companion animals and livestock animals. Pharmaceutical compositions and methods for using such compounds to treat such disorders are provided, as are methods for using such ligands for receptor localization studies.

  提供了公式I的杂环取代的喹啉-4-胺类似物。这些化合物是配体，可用于体内或体外调节特定受体活性，并且在治疗与人类、家养伴侣动物和家畜动物的病理性受体激活相关的疾病方面特别有用。提供了用于治疗此类疾病的制药组合物和方法，以及用于受体定位研究的配体使用方法。