8-(5'-dimethylamino-1'-naphthalene)sulfonamidoquinoline | 34532-50-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-(5'-dimethylamino-1'-naphthalene)sulfonamidoquinoline
• 英文别名: 5-(dimethylamino)-N-(quinolin-8-yl)naphthalene-1-sulfonamide；dansyl-8-aminoquinoline；8-(5-Dimethylaminonaphthalin-1-sulfonamiedo)chinolin；8-(5'-N,N-dimethylamino-1'-naphthalene)sulfonamidoquinoline；5-dimethylamino-naphthalene-1-sulfonic acid quinolin-8-ylamide；5-(dimethylamino)-N-(8-quinolinyl)-1-naphthalenesulfonamide；DANQUIN；Ds-HAQ；5-(dimethylamino)-N-quinolin-8-ylnaphthalene-1-sulfonamide
• CAS: 34532-50-8
• 化学式: C₂₁H₁₉N₃O₂S
• 分子量: 377.467
• InChiKey: JUKJASVEFRKWEH-UHFFFAOYSA-N

物化性质

• 熔点：
  147-151 °C
• 沸点：
  581.8±53.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  70.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  copper(II) acetate monohydrate 、 8-(5'-dimethylamino-1'-naphthalene)sulfonamidoquinoline 在 KOH 作用下， 以 丙酮 为溶剂， 以90%的产率得到bis(5-(dimethylamino)-N-(8-quinolinyl)-1-naphthalenesulfonamidato)copper(II) monohydrate
  参考文献：
  名称：

  Structural and fluorescent study of zinc complexes of dansyl aminoquinoline

  摘要：

  We have shown previously that 8-(5'-N,N-dimethylamino-1'-naphthalene)-sulfonamidoquinoline (DANQUIN) demonstrated a remarkable selectivity and sensitivity for the Zn(II) ion. In this work, the crystal structures of DANQUIN, Cu(DANQUIN)(2) and Cu(DANPY)(2) (DANPY, N-2-picolyl-(5'-NN-dimethylamino-1'-naphthalene)-sulfonamide) are reported and compared with the simulated structure of Zn(DANQUIN)(2), which is important for the understanding of the factors that govern the fluorescence of DANQUIN. Free DANQUIN mainly displays the fluorescence of the dansyl group at 547 nn while the Zn(II)-DANQUIN complex mainly shows the enhanced fluorescence of aminoquinoline at 469 nm, while the emission of the dansyl group shifted to 517 nm with an almost constant intensity. This result demonstrates the advantage of this hybrid fluorescent chemosensor for Zn(H), and also makes it a potential candidate for ratiometric Zn(II) detection. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2006.07.055
• 作为产物：
  描述：

  8-氨基喹啉 、 丹酰氯 生成 8-(5'-dimethylamino-1'-naphthalene)sulfonamidoquinoline
  参考文献：
  名称：

  Novel zinc fluorescent probe bearing dansyl and aminoquinoline groupsElectronic supplementary information (ESI) available: NMR spectra and assignment, UV titration details, crystal structure and competitive fluorescent experiments of L. See http://www.rsc.org/suppdata/cc/b2/b202976f/

  摘要：

  一种新型荧光化学传感器（L）对锌(II)离子表现出显著的选择性和灵敏性，这一点从溶液特性表征和使用Hela细胞系的体外实验中得到了证明。

  DOI：

  10.1039/b202976f

文献信息

• From Sensors to Silencers: Quinoline- and Benzimidazole-Sulfonamides as Inhibitors for Zinc Proteases
  作者：Matthieu Rouffet、César Augusto F. de Oliveira、Yael Udi、Arpita Agrawal、Irit Sagi、J. Andrew McCammon、Seth M. Cohen

  DOI：10.1021/ja101088j

  日期：2010.6.23

  sensors, chelating fragment libraries of quinoline- and benzimidazole-sulfonamides have been prepared and screened against several different zinc(II)-dependent matrix metalloproteinases (MMPs). The fragments show impressive inhibition of these metalloenzymes and preferences for different MMPs based on the nature of the chelating group. The findings show that focused chelator libraries are a powerful strategy

  源自小分子锌 (II) 离子传感器领域的广泛工作，已经制备了喹啉和苯并咪唑磺酰胺的螯合片段库，并针对几种不同的锌 (II) 依赖性基质金属蛋白酶 (MMP) 进行了筛选。基于螯合基团的性质，这些片段显示出对这些金属酶的显着抑制和对不同 MMP 的偏好。研究结果表明，聚焦螯合剂文库是发现用于金属蛋白抑制的先导片段的有力策略。
• Quinolinyl sulfonamides and sulphonyl esters exhibit inhibitory efficacy against New Delhi metallo-β-lactamase-1 (NDM-1)
  作者：Jia-Zhu Chigan、Zhenxin Hu、Lu Liu、Yin-Sui Xu、Huan-Huan Ding、Ke-Wu Yang

  DOI：10.1016/j.bioorg.2022.105654

  日期：2022.3

  effective MβL inhibitors to restore existing antibiotic efficacy is an ideal alternative. Although the serine-β-lactamase inhibitors have been used in clinical settings, MβL inhibitors are not available to date. In this work, thirty-one quinolinyl sulfonamides 1a-p and sulphonyl esters 2a-o were synthesized and assayed against MβL NDM-1. The obtained molecules specifically inhibited NDM-1, 1a-p and 2a-o

  由金属-β-内酰胺酶 (MβLs) 引起的“超级细菌”感染已发展成为新出现的健康威胁，开发有效的 MβL 抑制剂以恢复现有抗生素功效是一种理想的替代方案。尽管丝氨酸-β-内酰胺酶抑制剂已用于临床环境，但迄今为止还没有 MβL 抑制剂。在这项工作中，合成了 31 种喹啉基磺酰胺1a-p和磺酰酯2a-o，并针对 MβL NDM-1 进行了测定。所得分子特异性抑制NDM- 1、1a-p和2a-o的IC 50值分别为0.02-1.4和8.3-24.8 μM，1e和1f被发现是最有效的抑制剂，使用美罗培南 (MER) 作为底物时，IC 50为 0.02 μM。 构效关系表明取代苯基和带卤原子的苯基更显着地提高了喹啉衍生物对NDM-1的抑制作用。1a-p使用 NDM-1、EC01 和 EC08恢复了 MER 对大肠杆菌的抗菌作用，导致 MIC 值降低 2-64 倍。最重要的是，1e在单次腹膜内给药后，协同
• Fluorescent Nitric Oxide Detection by Copper Complexes Bearing Anthracenyl and Dansyl Fluorophore Ligands
  作者：Mi Hee Lim、Stephen J. Lippard

  DOI：10.1021/ic0609913

  日期：2006.10.30

  Anthrancenyl and dansyl fluorophore ligands [AnCH(2)pipCS(2)K (1), Ds-Hen (2), Ds-HAMP (3), Ds-HAQ (4), and Ds-HAPP (5)] were prepared for coordination to Cu-II. Five Cu complexes, [Cu(AnCH(2)pipCS(2))(2)] (6), [Cu(Ds-en)(2)] (7), [Cu(Ds-AMP)(2)] (8), [Cu(Ds-AQ)(2)] (9), and [Cu(Ds-APP)(OTf)] (10), were synthesized as candidates for detecting nitric oxide (NO) by fluorescence and characterized by X-ray crystallography. A decrease in fluorescence compared to that of the free ligands (1-5) was measured following the formation of the corresponding five Cu-II complexes 6-10. Fluorescence was restored in the presence of NO in CH3OH/CH2Cl2 solutions of the compounds. Complexes 7, 8, and 10 exhibited a fluorescence response to NO in pH 7.0 or 9.0 buffered aqueous solutions. Spectroscopic studies revealed that NO-induced fluorescence enhancement in these Cu-II complexes occurs by reduction to Cu-I. The present studies demonstrate that Cu-II complexes are effective as fluorescent probes for detecting NO in both organic and aqueous environments.
• Dansyl-8-aminoquinoline as a sensitive pH fluorescent probe with dual-responsive ranges in aqueous solutions
  作者：Min Zhang、Shuyu Zheng、Liguo Ma、Meili Zhao、Lengfang Deng、Liting Yang、Li-Jun Ma

  DOI：10.1016/j.saa.2013.12.062

  日期：2014.4

  A sensitive pH fluorescent probe based on dansyl group, dansy1-8-aminoquinoline (DAQ), has been synthesized. The probe showed dual-responsive ranges to pH changes, one range from 2.00 to 7.95 and another one from 7.95 to 10.87 in aqueous solution, as it showed pK(a) values of 5.73 and 8.56 under acid and basic conditions, respectively. Furthermore, the pH response mechanism of the probe was explored successfully by using NMR spectra. The results indicated that the responses of DAQ to pH changes should attribute to the protonation of the nitrogen atom in the dimethylamino group and deprotonation of sulfonamide group. (c) 2014 Published by Elsevier B.V.
• COMPOSITION AND METHODS FOR THE DESIGN AND DEVELOPMENT OF METALLO-ENZYME INHIBITORS
  申请人：Pellecchia Maurizio

  公开号：US20100041653A1

  公开（公告）日：2010-02-18

  The present disclosure provides compounds having the general structure A or pharmaceutically acceptable salts thereof: R—X  (A) wherein R is an alkyl or aryl moiety comprising heterocyclic structures; and X is a metal-chelatin group selected from: This disclosure further provides a focused library of compounds for use in the discovery and design of metallo-enzyme inhibitors. This fragment-based approach provides an assembly of a library of low molecular weight compounds (MW<300 Da) containing a variety of potential metal-chelating groups. The identification of the inhibitory scaffolds among these compounds provides the initial hit fragments that may be optimized for affinity against a particular target using common medicinal chemistry, structure-based or NMR-based approaches.