4-cyano-N-(quinolin-8-yl)benzenesulfonamide | 1177645-79-2

• 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: 4-cyano-N-(quinolin-8-yl)benzenesulfonamide
• 英文别名: 4-cyano-N-quinolin-8-ylbenzenesulfonamide
• CAS: 1177645-79-2
• 化学式: C₁₆H₁₁N₃O₂S
• 分子量: 309.348
• InChiKey: PMMQESBFNMBBAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-cyano-N-(quinolin-8-yl)benzenesulfonamide 在 碘 、 sodium acetate 、 nickel(II) acetate tetrahydrate 作用下， 以 1,2-二氯乙烷 为溶剂， 以74 %的产率得到4-cyano-N-(5-iodoquinolin-8-yl)benzenesulfonamide
  参考文献：
  名称：

  Ni 催化的区域选择性 C-5 卤化 8-氨基喹啉和共催化螯合辅助芳香磺胺的 C−H 碘化与分子碘

  摘要：

  首次报道了使用廉价且温和的分子碘 (I 2 ) 作为碘化试剂的区域选择性 Ni(II )- 和 Co(II)- 催化的磺胺类药物顺序碘化。

  DOI：

  10.1002/asia.202200874
• 作为产物：
  描述：

  2-硝基苯胺 在 甲烷 、 一水合肼 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.25h， 生成 4-cyano-N-(quinolin-8-yl)benzenesulfonamide
  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

• 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。
• Sodium chlorate as a viable substoichiometric oxidant for cobalt-catalyzed oxidative annulation of aryl sulfonamides with alkynes
  作者：You Ran、Yudong Yang、Luoqiang Zhang

  DOI：10.1016/j.tetlet.2016.06.059

  日期：2016.7

  for the first time as an efficient and versatile oxidant in the catalytic C–H activation reaction. By using sodium chlorate as the oxidant, a highly regioselective cobalt-catalyzed oxidative annulation of aryl sulfonamides with alkynes has been developed and can be extended to the annulation of benzamide.

  在这项工作中，NaClO 3首次被证明是催化C–H活化反应中的一种高效通用氧化剂。通过使用氯酸钠作为氧化剂，已经开发出具有区域选择性的钴催化的芳基磺酰胺与炔烃的氧化环合反应，并且可以扩展到苯甲酰胺的环合反应中。
• Rhodium(<scp>i</scp>)-catalyzed mono-selective C–H alkylation of benzenesulfonamides with terminal alkenes
  作者：Supriya Rej、Naoto Chatani

  DOI：10.1039/c9cc05219d

  日期：——

  The Rh(I)-catalyzed ortho-alkylation of benzenesulfonamides with alkenes with the aid of an 8-aminoquinoline directing group is reported. The reaction is applicable to a variety of benzenesulfonamide derivatives and various alkenes. Curiously, unactivated 1-alkenes were more reactive than activated alkenes. Deuterium labeling experiments indicate that an unusual 1,2-H shift mechanism to generate a

  报道了借助于8-氨基喹啉引导基团的Rh（I）催化的苯磺酰胺与烯烃的邻烷基化。该反应适用于各种苯磺酰胺衍生物和各种烯烃。奇怪的是，未活化的1-烯烃比活化的烯烃更具反应性。氘标记实验表明，涉及一种不寻常的1,2-H移位机理，可生成卡宾铑中间体。
• Metal-Binding Pharmacophore Library Yields the Discovery of a Glyoxalase 1 Inhibitor
  作者：Christian Perez、Amanda M. Barkley-Levenson、Benjamin L. Dick、Peter F. Glatt、Yadira Martinez、Dionicio Siegel、Jeremiah D. Momper、Abraham A. Palmer、Seth M. Cohen

  DOI：10.1021/acs.jmedchem.8b01868

  日期：2019.2.14

  8-(methylsulfonylamino)quinoline (8-MSQ) was identified as a hit. Through computational modeling and synthetic elaboration, a potent GLO1 inhibitor was developed with a novel sulfonamide core pharmacophore. A lead compound was demonstrated to penetrate the blood-brain barrier, elevate levels of methylglyoxal in the brain, and reduce depression-like behavior in mice. These findings provide the basis

  焦虑和抑郁是常见的高度共病的精神疾病，占全世界医学残疾的很大比例。乙二醛酶1（GLO1）已被确定为治疗焦虑症和抑郁症的可能靶标。GLO1是一种Zn2 +依赖性酶，可将由谷胱甘肽和甲基乙二醛形成的半硫缩醛异构化为乳酸硫酯。为了开发GLO1的活性抑制剂，基于片段的药物发现被用于鉴定可用作铅开发核心支架的片段。在筛选了聚焦于金属结合药效基团的文库后，鉴定出了8-（甲基磺酰基氨基）喹啉（8-MSQ）。通过计算建模和合成，开发了一种具有新型磺酰胺核心药效基团的有效GLO1抑制剂。铅化合物被证明可以穿透血脑屏障，提高大脑中甲基乙二醛的水平，并减少小鼠的抑郁样行为。这些发现为GLO1抑制剂治疗抑郁症和相关的精神疾病提供了依据。
• 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.