3'-chloro-4-nitrobenzenesulfonanilide | 16937-05-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3'-chloro-4-nitrobenzenesulfonanilide
• 英文别名: 4-Nitro-benzolsulfon-N-(3-chlor-phenyl)-amid；N-(3-chlorophenyl)-4-nitrobenzenesulfonamide
• CAS: 16937-05-6
• 化学式: C₁₂H₉ClN₂O₄S
• mdl: MFCD00705164
• 分子量: 312.733
• InChiKey: REAXFDPZKNULSH-UHFFFAOYSA-N

物化性质

• 熔点：
  146-147 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  482.7±55.0 °C(Predicted)
• 密度：
  1.545±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3'-chloro-4-nitrobenzenesulfonanilide 在 盐酸 、 tin 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以93%的产率得到4-氨基-N-(3-氯苯基)-苯磺酰胺
  参考文献：
  名称：

  Analgesic agents without gastric damage: Design and synthesis of structurally simple benzenesulfonanilide-type cyclooxygenase-1-selective inhibitors

  摘要：

  In order to create novel analgesic agents without gastric disturbance, structurally simple cyclooxygenase-1 (COX-1) inhibitors with a benzenesulfonanilide skeleton were designed and synthesized. As a result, compounds 11f and 15a, which possess a p-amino group on the benzenesulfonyl moiety and p-chloro group on the anilino moiety, showed COX-1-selective inhibition. Moreover compound 11f, which is the most potent compound in this study showed more potent analgesic activity than that of aspirin at 30 mg/kg by po. The anti-inflammatory activity and gastric damage, however, were very weak or not detectably different from aspirin. Since the structure of our COX-1 inhibitors are very simple, they may be useful as lead compounds for superior COX-1 inhibitors as analgesic agents without gastric disturbance. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2006.10.029
• 作为产物：
  描述：

  p-Nitrobenzolsulfonylbromid 、 3-氯苯胺 在 吡啶 作用下， 以 硝基苯 为溶剂， 生成 3'-chloro-4-nitrobenzenesulfonanilide
  参考文献：
  名称：

  Litvinenko, L. M.; Shatskaya, V. A.; Savelova, V. A., Doklady Chemistry, 1982, vol. 265, p. 199 - 204

  摘要：

  DOI：

文献信息

• Base‐Promoted Michael Addition/Smiles Rearrangement/ <i>N</i> ‐Arylation Cascade: One‐Step Synthesis of 1,2,3‐Trisubstituted 4‐Quinolones from Ynones and Sulfonamides
  作者：Jing Liu、Dan Ba、Weiwei Lv、Yanhui Chen、Zemin Zhao、Guolin Cheng

  DOI：10.1002/adsc.201900960

  日期：2020.1.7

  synthesize 1,2,3‐trisubstituted 4‐quinolones from readily available ynones and sulfonamides was developed. The construction of one C−C bond and two C−N bonds via cleavage of one N−S, one C−S, and one C−X (X=F, Cl, Br, O) bond is achieved under transition‐metal‐free conditions in one step. This transformation generates 1 equiv. of sulfur dioxide and 1 equiv. of hydrogen halide as the byproducts. The broad substrate

  已开发了一种通用，实用且环保的方案，可以从容易获得的炔酮和磺酰胺中合成1,2,3-三取代的4-喹诺酮。在过渡金属的作用下，通过裂解一个N-S，一个C-S和一个C-X（X = F，Cl，Br，O）键，可以构建一个C-C键和两个C-N键。一步就能达到无条件。此变换生成1个当量。二氧化硫和1当量 卤化氢作为副产物。1,2,3-三取代的4-喹诺酮类化合物的52个实例证明了广泛的底物范围和官能团耐受性。初步的机理研究支持顺序的迈克尔加成/微笑重排/ N芳基化反应途径。
• [EN] SELECTIVE INHIBITORS OF 12(S)-LIPOXYGENASE (12-LOX) AND METHODS FOR USE OF THE SAME<br/>[FR] INHIBITEURS SÉLECTIFS DE 12(S)-LIPOXYGÉNASE (12-LOX) ET PROCÉDÉS D'UTILISATION CORRESPONDANTS
  申请人：UNIV MICHIGAN REGENTS

  公开号：WO2019204375A1

  公开（公告）日：2019-10-24

  Disclosed herein are small molecule inhibitors of 12(S)-Lipoxygenase (12-LOX), and methods of using the small molecules to inhibit 12-LOX activation and to treat diseases, such as platelet hemostasis and thrombosis. In particular, disclosed herein are compounds of Formula (I) and pharmaceutically acceptable salts thereof: wherein the substituents are as described.

  本文揭示了12（S）-脂氧合酶（12-LOX）的小分子抑制剂，以及使用这些小分子抑制12-LOX激活和治疗疾病（如血小板止血和血栓形成）的方法。特别地，本文揭示了式（I）的化合物及其药物可接受的盐：其中取代基如所述。
• [EN] PLASMA KALLIKREIN INHIBITORS<br/>[FR] INHIBITEURS DE LA KALLICRÉINE PLASMATIQUE
  申请人：SHIRE HUMAN GENETIC THERAPIES

  公开号：WO2022197756A1

  公开（公告）日：2022-09-22

  The present invention provides compounds and compositions thereof which are useful as inhibitors of plasma kallikrein and which exhibit desirable characteristics for the same.

  本发明提供了一些化合物及其组合物，这些化合物可用作血浆卡利肌酶的抑制剂，并且具有相应的理想特性。
• Traceless N‐Polyfluoroalkylation of Weakly Nucleophilic Nitrogen Containing Compounds
  作者：Laura Santos、Florian Audet、Morgan Donnard、Armen Panossian、Jean-Pierre Vors、David Bernier、Sergii Pazenok、Frederic R. Leroux

  DOI：10.1002/chem.202300792

  日期：——

  the high cost, toxicity or environmental impact of commonly used polyfluoroalkylation reagents. We report the sulfuryl fluoride (SO2F2)-mediated N-polyfluoroalkylation of weakly nucleophilic nitrogen compounds from readily available fluorinated alcohols. This method opens access to a variety of N-polyfluoroalkylated building blocks that are highly valuable for life science applications.

  由于常用多氟烷基化试剂的高成本、毒性或环境影响， N-多氟烷基化反应具有挑战性。我们报告了硫酰氟 (SO 2 F 2 ) 介导的弱亲核氮化合物的N -多氟烷基化，这些化合物来自现成的氟化醇。该方法开启了对各种N-多氟烷基化构建块的访问，这些构建块对生命科学应用具有很高的价值。
• Selective inhibitors of 12(S)-lipoxygenase (12-LOX) and methods for use of the same
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US11236044B2

  公开（公告）日：2022-02-01

  Disclosed herein are small molecule inhibitors of 12(S)-Lipoxygenase (12-LOX), and methods of using the small molecules to inhibit 12-LOX activation and to treat diseases, such as platelet hemostasis and thrombosis. In particular, disclosed herein are compounds of Formula (I) and pharmaceutically acceptable salts thereof: wherein the substituents are as described.

  本文公开了12(S)-脂氧合酶（12-LOX）的小分子抑制剂，以及使用这些小分子抑制12-LOX活化和治疗疾病（如血小板止血和血栓形成）的方法。特别地，本文公开了式(I)化合物及其药学上可接受的盐：其中取代基如所述。