N-quinoline-8-yl-4-n-propylbenzenesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-quinoline-8-yl-4-n-propylbenzenesulfonamide
• 英文别名: 4-propyl-N-(quinolin-8-yl)benzenesulfonamide；4-n-Propyl-N-(8-quinolyl)benzenesulfonamide；4-propyl-N-quinolin-8-ylbenzenesulfonamide
• 化学式: C₁₈H₁₈N₂O₂S
• 分子量: 326.419
• InChiKey: RVCAZHUIUDKZEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-quinoline-8-yl-4-n-propylbenzenesulfonamide 、 3-甲基-1,2-丁二烯 在 cobalt(II) acetate 、 manganese(III) triacetate dihydrate 、 特戊酸钠 作用下， 以 2,2,2-三氟乙醇 为溶剂， 以22%的产率得到3-(propan-2-ylidene)-6-propyl-2-(quinolin-8-yl)-3,4-dihydro-2H-benzo[e][1,2]thiazine 1,1-dioxide
  参考文献：
  名称：

  钴催化的芳基CH活化和磺胺类与烯类的高度区域选择性分子间环化。

  摘要：

  在本文中，我们描述了芳基和杂芳基磺酰胺的钴催化CH活化及其与艾伦的分子间杂环化反应，为生物有趣的杂环的合成提供了收敛策略。

  DOI：

  10.1039/c6cc08622e
• 作为产物：
  描述：

  8-氨基喹啉 、 4-正丙基苯磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以82%的产率得到N-quinoline-8-yl-4-n-propylbenzenesulfonamide
  参考文献：
  名称：

  含带吡啶环的芳香族磺​​酰胺的半夹心钌配合物的合成和表征：苯乙酮衍生物转移氢化的催化剂

  摘要：

  N-(喹啉-8-基-芳基)苯磺酰胺1-6是通过8-氨基喹啉和各种苯磺酰氯的反应成功合成的。然后，由 1-6 与 [RuCl2(p-cymene)]2 的反应制备半夹心钌配合物 7-12。合成的化合物通过NMR和FTIR光谱和元素分析进行​​表征，化合物8和9进一步通过X射线衍射进行分析。在 KOH 存在下，以 2-丙醇（作为氢源）在 82°C 条件下，该配合物在苯乙酮衍生物向苯乙醇的转移氢化中作为催化剂的效率进行了筛选，并且它们都表现出良好的活性。复合物 10 和 12 是最活跃的（周转频率值：分别为 703 和 734 h-1）。

  DOI：

  10.1002/ejic.201300266

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。
• Synthesis, in vitro β -glucuronidase inhibitory potential and molecular docking studies of quinolines
  作者：Bilquees Bano、Arshia、Khalid Mohammed Khan、Kanwal、Bibi Fatima、Muhammad Taha、Nor Hadiani Ismail、Abdul Wadood、Mehreen Ghufran、Shahnaz Perveen

  DOI：10.1016/j.ejmech.2017.08.052

  日期：2017.10

  In this study synthesis and β-glucuronidase inhibitory potential of 3/5/8 sulfonamide and 8-sulfonate derivatives of quinoline (1–40) are discussed. Studies reveal that all the synthetic compounds were found to have good inhibitory activity against β-glucuronidase. Nonetheless, compounds 1, 2, 5, 13, and 22–24 having IC50 values in the range of 1.60–8.40 μM showed superior activity than the standard

  在这项研究中合成和β葡萄糖醛酸酶喹啉（的3/5/8磺酰胺和8-磺酸酯衍生物的抑制潜力1-40）进行了讨论。研究表明，所有合成的化合物均对β-葡萄糖醛酸苷酶具有良好的抑制活性。尽管如此，化合物1，2，5，13，和22 - 24个具有IC 50值的1.60-8.40的范围内 μ中号显示出比标准糖酸-1,4-内酯优良的活性（IC 50  = 48.4±1.25  μM）。此外，还对选定化合物进行了分子对接研究，以观察活性化合物与结合位点之间的相互作用。通过1 H NMR，EI-MS和HREI-MS光谱技术确认了所有合成化合物的结构。
• Synthesis and Characterization of Half‐Sandwich Ruthenium Complexes Containing Aromatic Sulfonamides Bearing Pyr­id­inyl Rings: Catalysts for Transfer Hydrogenation of Acetophenone Derivatives
  作者：Serkan Dayan、Nilgun Ozpozan Kalaycioglu、Jean‐Claude Daran、Agnès Labande、Rinaldo Poli

  DOI：10.1002/ejic.201300266

  日期：2013.6.12

  half-sandwich ruthenium complexes 7–12 were prepared from the reactions of 1–6 with [RuCl2(p-cymene)]2. The synthesized compounds were characterized by NMR and FTIR spectroscopy and elemental analysis, and compounds 8 and 9 were further analyzed by X-ray diffraction. The complexes were screened for their efficiency as catalysts in the transfer hydrogenation of acetophenone derivatives to phenylethanols

  N-(喹啉-8-基-芳基)苯磺酰胺1-6是通过8-氨基喹啉和各种苯磺酰氯的反应成功合成的。然后，由 1-6 与 [RuCl2(p-cymene)]2 的反应制备半夹心钌配合物 7-12。合成的化合物通过NMR和FTIR光谱和元素分析进行​​表征，化合物8和9进一步通过X射线衍射进行分析。在 KOH 存在下，以 2-丙醇（作为氢源）在 82°C 条件下，该配合物在苯乙酮衍生物向苯乙醇的转移氢化中作为催化剂的效率进行了筛选，并且它们都表现出良好的活性。复合物 10 和 12 是最活跃的（周转频率值：分别为 703 和 734 h-1）。
• Performance improvement of Ru II complexes pyridinyl backbone on dye-sensitized solar cells (DSSC)
  作者：Serkan Dayan、Nilgün Kalaycıoğlu Özpozan

  DOI：10.1016/j.ica.2018.01.021

  日期：2018.4

  Two new series of Ru-II complexes (6-10 bearing an imine bond and 16-20 bearing a sulfonamidate fragment) based 8-aminoquinoline backbone were prepared and characterized by NMR. FT-IR, elemental analysis, UV-vis, CV etc. and tested as a photoactive dye for dye-sensitized solar cells (DSSC).The performance of the Ru-II-arene containing imine bond complex types (6-10) as a dye on DSSCs produced cells with power conversion efficiencies (PCEs) of around 0.03-0.10%. The [(N-Quinoline-8-yl-benzenesulfonamido)(p-cyrnene)chlororuthenium(II)] (SD-E1311) complex, which we previously produced was tested instead of the complexes bearing the imine bond (6-10) and its PCE for SD-E1311 was found as 0.12%. Herein, the increase of the Voc is quite interesting and, for this reason, the sulfonamidate based complexes were selected for the backbone structure.To enhance immobilization to the titanium oxide layer and solubility and electron injection of the corresponding excited dye on the DSSC process, 2,2'-bipyridine-4,4'-dicarboxylic acid as the anchor group and thiocyanate ligands were selected instead of p-cyrnene and chloro ligands over the sulfonamidate complex. Then, the photoactive dye properties of the new Re complexes (16-20) were investigated and the results showed that the 16-20 dyes bearing sulfonamidate, carboxylic anchoring and thiocyanate fragments benefited the short-circuit current and the open-circuit voltage, and had PCEs of 1.26%, 1.08%, 1.58%, 0.90% and 1.36% under A1141.5G irradiation, respectively. The working devices, results also show that the 16-20 dyes demonstrated average performances with a PCEmax of 1.58% which was occurred with 18 complex. (C) 2018 Elsevier B.V. All rights reserved.
• Synthesis and in vitro evaluation of leishmanicidal and trypanocidal activities of N-quinolin-8-yl-arylsulfonamides
  作者：Luiz Everson da Silva、Antônio Carlos Joussef、Letícia Kramer Pacheco、Daniela Gaspar da Silva、Mário Steindel、Ricardo Andrade Rebelo

  DOI：10.1016/j.bmc.2007.09.007

  日期：2007.12

  In the present paper 12 N-quinolin-8-yl-arylsulfonamides synthesized by coupling 8-aminoquinolines with various arylsulfonylchlorides were assayed in vitro against Leishmania amazonensis, L. chagasi and Trypanosoma cruzi strains. This series of new compounds were found to be selective for Leishmania spp. promastigote and amastigote forms. The most active compound was the N-(8-quinolyl)-3,5-diflu. uoro-benzenesulfonamide 10 with an IC50 against L. amazonensis and L. chagasi of 2.12 and 0.45 mu M, respectively. The less cytotoxic biphenyl derivative 7 was very e. ffective against intracellular L. amazonensis with a reduction of macrophage cell infection of 82.1% at 25 mu M. In addition, a copper complex 17 of an inactive ligand was readily synthesized and showed high leishmanicidal and trypanocidal activity against both extra and intracellular forms. (c) 2007 Elsevier Ltd. All rights reserved.