N-(6-甲氧基-8-喹啉基)对甲苯磺酰胺 | 109628-27-5

• 物质功能分类: 生物化工 - 生化试剂 - 荧光成像
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(6-甲氧基-8-喹啉基)对甲苯磺酰胺
• 中文别名: N-(6-甲氧-8-喹啉基)-P-对甲苯磺酰甲基亚硝酰胺
• 英文名称: N-(6-methoxy-8-quinolinyl)-4-methylbenzenesulfonamide
• 英文别名: N-(6-methoxyquinolin-8-yl)-4-methylbenzenesulfonamide；N-(6-methoxy-8-quinolyl)-p-toluenesulfonamide；6-methoxy-8-(p-toluenesulfonamido)-quinoline；6-methoxy-8-p-toluenesulfonamidoquinoline；6-methoxy-8-tosylsulfonamidoquinoline；6-methoxy-8-p-toluenesulfonamido-quinoline；N-(6-Methoxy-8-quinolyl)-4-toluenesulfonamide
• CAS: 109628-27-5
• 化学式: C₁₇H₁₆N₂O₃S
• mdl: MFCD00467847
• 分子量: 328.392
• InChiKey: HKRNYOZJJMFDBV-UHFFFAOYSA-N

物化性质

• 熔点：
  133–134 ℃
• 溶解度：
  溶于乙醇、甲醇
• 最大波长(λmax)：
  334 nm
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(6-甲氧基-8-喹啉基)对甲苯磺酰胺 在 copper diacetate 、 三溴化硼 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 43.5h， 生成 N-(6-(4-methoxyphenoxy)quinolin-8-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Developing structure–activity relationships from an HTS hit for inhibition of the Cks1–Skp2 protein–protein interaction

  摘要：

  Structure-activity relationships have been developed around 5-bromo-8-toluylsulfonamidoquinoline 1 a hit compound in an assay for the interaction of the E3 ligase Skp2 with Cks1, part of the SCF ligase complex. Disruption of this protein-protein interaction results in higher levels of CDK inhibitor p27, which can act as a tumor suppressor. The results of the SAR developed highlight the relationship between the sulfonamide and quinoline nitrogen, while also suggesting that an aryl substituent at the 5-position of the quinoline ring contributes to the potency in the interaction assay. Compounds showing potency in the interaction assay result in greater levels of p27 and have been shown to inhibit cell growth of two p27 sensitive tumor cell lines. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.067
• 作为产物：
  描述：

  6-甲氧基-8-硝基喹啉 在 甲烷 、 一水合肼 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 N-(6-甲氧基-8-喹啉基)对甲苯磺酰胺
  参考文献：
  名称：

  Visible Light-Promoted Photocatalytic C-5 Carboxylation of 8-Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer Pathway

  摘要：

  An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated ^•CBr₃ radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.

  DOI：

  10.1021/acs.joc.9b00942

文献信息

• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：UNIV OSLO

  公开号：WO2018033719A1

  公开（公告）日：2018-02-22

  The invention provides compounds for use in a method of treating and/or preventing a bacterial infection in a human or non-human mammal, said method comprising administration of said compound in combination with (either simultaneously, separately, or sequentially) a β-lactam antibiotic, wherein said compound has the general formula I: (I) (wherein: Q is a lipophilic, zinc chelating moiety which is selective for Zn2+ ions and which comprises at least one, preferably two or more (e.g 2, 3 or 4), optionally substituted, unsaturated heterocyclic rings, e.g. 5 or 6-membered heterocyclic rings (such rings preferably include at least one heteroatom selected from N, S and O, preferably N); wherein any optional substituents may be selected from C1-6 alkyl, C1-6 alkoxy, halogen, nitro, cyano, amine, and substituted amine; each L, which may be the same or different, is a covalent bond or a linker; each W, which may be the same or different, is a non-peptidic hydrophilic group which comprises one or more hydroxy groups; and x is an integer from 1 to 3) or a stereoisomer, pharmaceutically acceptable salt or prodrug thereof.

  该发明提供了一种化合物，用于治疗和/或预防人类或非人哺乳动物体内的细菌感染，所述方法包括将该化合物与β-内酰胺类抗生素（可以同时、分开或顺序地）结合给药，其中所述化合物具有一般式I：（I）（其中：Q是一个亲脂性、选择性结合Zn2+离子的基团，包括至少一个，最好是两个或更多（例如2、3或4个），可选择地取代的不饱和杂环环，例如5或6元杂环环（这些环最好包括至少一个从N、S和O中选择的杂原子，最好是N）；其中任何可选择的取代基可以选择自C1-6烷基、C1-6烷氧基、卤素、硝基、氰基、胺和取代胺；每个L，可以相同也可以不同，是一个共价键或一个连接基；每个W，可以相同也可以不同，是一个非肽性亲水基团，包括一个或多个羟基；x是1到3之间的整数）或其立体异构体、药学上可接受的盐或前药。
• Copper‐Catalyzed C‐4 Carboxylation of 1‐Naphthylamide Derivatives with CBr ₄ /MeOH
  作者：Tapan Sahoo、Chiranjit Sen、Harshvardhan Singh、E. Suresh、Subhash Chandra Ghosh

  DOI：10.1002/adsc.201900482

  日期：2019.9.3

  A simple and practical copper catalyzed C‐4 carboxylation reaction of 1‐naphthylamide derivatives using carbon tetra bromide and methanol is reported here. Picolinamide and its derivatives are used as a bidentate directing group for the distal C4‐H functionalization. Various substituted naphthylamide derivatives, and anilides are employed for the carboxylation and proceeds in good yields under mild

  本文报道了使用四溴化碳和甲醇进行简单而实用的铜催化的1-萘酰胺衍生物的C-4羧化反应。Picolinamide及其衍生物用作远端C4-H功能化的双齿引导基团。各种取代的萘酰胺衍生物和苯甲酸酯被用于羧化反应，并在温和的条件下以高收率进行。从实验结果可以看出，1-萘甲酰胺的C4-H羧化反应可能通过单电子转移（SET）途径进行。
• [EN] INHIBITORS OF METALLO-BETA-LACTAMASE (MBL) COMPRISING A ZINC CHELATING MOIETY<br/>[FR] INHIBITEURS DE MÉTALLO-BÊTA-LACTAMASE (MBL) COMPRENANT UNE FRACTION DE CHÉLATION DU ZINC
  申请人：UNI I OSLO

  公开号：WO2015049546A1

  公开（公告）日：2015-04-09

  The invention provides compounds according to formula I: A - L - B wherein A represents a lipophilic chelating moiety which is selective for Zn2+ ions; L is a covalent bond or a linker; and B is a vector which is either a moiety capable of interacting with one or more biological structures found in a bacterium (preferably in a bacterial cell wall), for example a penicillin-binding protein such as a metallo-β- lactamase or DD-transferase, or a moiety capable of enhancing transport of the compound across a bacterial cell membrane. Such compounds find use in a method of treating and/or preventing a bacterial infection in a human or non-human mammal. In such a method, the compound of formula I may be administered in combination with (either simultaneously, separately, or sequentially) a β-lactam antibiotic.

  该发明提供了符合以下公式I的化合物：A - L - B，其中A代表选择性对Zn2+离子的亲脂螯合基团；L是共价键或连接物；B是矢量，可以是能与细菌中的一个或多个生物结构相互作用的基团（最好是在细菌细胞壁中找到的），例如金黄色葡萄球菌结合蛋白（例如金属β-内酰胺酶或DD-转移酶），或者是能增强化合物穿过细菌细胞膜的基团。这种化合物可用于治疗和/或预防人类或非人哺乳动物的细菌感染的方法。在这种方法中，公式I的化合物可以与（同时、分开或顺序地）β-内酰胺类抗生素一起给予。
• NEUROPROTECTIVE QUINOLINE SULFONAMIDES
  申请人：Dahl Russell

  公开号：US20200188706A1

  公开（公告）日：2020-06-18

  Disclosed herein are methods and compositions comprising compounds capable of activating and increasing protein SUMOylation. Disclosed herein are methods and compositions comprising compounds capable of showing neuroprotective and cytoprotective effects when administered to injured cells. Also disclosed are methods comprising these compounds for treating neuronal or neurological disorders, including Alzheimer's disease, Parkinson's disease, Huntington's disease, fronto-temporal dementia, chronic traumatic encepholopathy, traumatic brain injury, or stroke.

  本文揭示了一种包括能够激活和增加蛋白质SUMO化的化合物的方法和组合物。本文还揭示了一种包括具有神经保护和细胞保护作用的化合物的方法和组合物，当这些化合物被施用于受伤细胞时。还揭示了一种包括这些化合物的方法，用于治疗神经元或神经系统疾病，包括阿尔茨海默病、帕金森病、亨廷顿病、额颞型痴呆、慢性创伤性脑病、创伤性脑损伤或中风。
• ZINC INDICATORS FOR CELLULAR IMAGING
  申请人：The Board of Regents of the University of Texas System

  公开号：US20200131160A1

  公开（公告）日：2020-04-30

  The present disclosure provides compounds of the formula: wherein the variables are defined herein. The present disclosure also provides methods of imaging Zn 2+ within granules in cells, such as pancreatic α-, β-, and δ-cells. The present disclosure also provides methods of sorting cells comprising the use of the compounds of the present disclosure.

  本公开提供了以下式的化合物： 其中变量在此处定义。本公开还提供了在细胞内成团成分Zn2+的成像方法，例如胰腺α-、β-和δ-细胞。本公开还提供了利用本公开的化合物对细胞进行排序的方法。