N-[3,5-bis(trifluoromethyl)phenyl]-4-nitrobenzenesulfonamide | 587-57-5

• 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: N-[3,5-bis(trifluoromethyl)phenyl]-4-nitrobenzenesulfonamide
• 英文别名: 4-nitro-benzenesulfonic acid-(3,5-bis-trifluoromethyl-anilide)；4-Nitro-benzolsulfonsaeure-(3,5-bis-trifluormethyl-anilid)
• CAS: 587-57-5
• 化学式: C₁₄H₈F₆N₂O₄S
• 分子量: 414.285
• InChiKey: RLKYXKSPNGXWJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-[3,5-bis(trifluoromethyl)phenyl]-4-nitrobenzenesulfonamide 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 生成 N-[3,5-bis(trifluoromethyl)phenyl]-4-(methanesulfonamido)benzenesulfonamide
  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：

  间二(三氟甲基)苯胺 、 对硝基苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以25%的产率得到N-[3,5-bis(trifluoromethyl)phenyl]-4-nitrobenzenesulfonamide
  参考文献：
  名称：

  针对主要社区相关耐甲氧西林金黄色葡萄球菌菌株USA300的吸电子取代苯磺酰胺

  摘要：

  摘要合成了由磺酰胺组成的小型聚焦化学文库。这些化合物被设计为缺乏通常在磺酰胺抗生素中发现的对氨基苯部分。使用磁盘扩散和微量稀释试验研究了这些合成化合物对全球主要耐甲氧西林金黄色葡萄球菌（MRSA）菌株USA300（SF8300）和金黄色葡萄球菌（S. aureus）对照菌株ATCC 25923和ATCC 29213的抗菌活性。根据药敏结果，可检测到强力的金黄色葡萄球菌和MRSA USA300生长抑制剂，例如N发现具有最低抑制浓度（MIC）低至5.6μg/ cm 3的-[3,5-双（三氟甲基）苯基] -4-溴苯磺酰胺以及其他有效的磺酰胺。结构与活性的关系表明，这些脱氨基苯磺酰胺需要吸电子取代基才能有效抑制细菌病原体的生长。另外，即使当细菌叶酸合成中间体p时，它们仍具有抑制金黄色葡萄球菌菌株生长的能力。-氨基苯甲酸（PABA）被补充，而PABA补充则完全削弱了已知的磺胺药，磺胺甲恶唑的抗菌活性

  DOI：

  10.1007/s00706-013-0937-3

文献信息

• [EN] BISARYLSULFONAMIDE COMPOUNDS AND THEIR USE IN CANCER THERAPY<br/>[FR] COMPOSES DE BISARYLSULFONAMIDE ET LEUR UTILISATION DANS LE TRAITEMENT DU CANCER
  申请人：CYCLACEL LTD

  公开号：WO2004005278A1

  公开（公告）日：2004-01-15

  The present invention relates to the use of bisarylsulfonamide compounds of formula (I) wherein W is a CI-5 branched or unbranched alkyl group or a C2-5 alkenyl group; nis0or1; R1 is H, a C, 1-8 branched or unbranched alkyl group, a C2-8 alkenyl group, or an aryl or aralkyl group; Ar1 is a substituted thienyl, furyl, pyrrolyl, imidazothiazolyl, thiazolyl, pyridyl or phenyl group; and Ar2 is a substituted phenyl, indolyl or benzoimidazolyl group; in the preparation of a medicament for treating proliferative disorders. Further aspects of the invention relate to compounds of formula (I), pharmaceutical compositions thereof, and an assay for determining binding to HDM2.

  本发明涉及使用公式（I）中的双芳基磺酰胺化合物，其中W是CI-5支链或直链烷基或C2-5烯基基团；n为0或1；R1为H，C1-8支链或直链烷基，C2-8烯基基团，或芳基或芳基烷基团；Ar1为取代噻吩基，呋喃基，吡咯基，咪唑硫唑基，噻唑基，吡啶基或苯基；Ar2为取代苯基，吲哚基或苯并咪唑基团，在制备用于治疗增殖性疾病的药物方面。本发明的其他方面涉及公式（I）的化合物，其制药组合物以及用于确定与HDM2结合的测定方法。
• Bisarylsulfonamide compounds and their use in cancer therapy
  申请人：Wang Shudong

  公开号：US20050215548A1

  公开（公告）日：2005-09-29

  The present invention relates to the use of bisarylsulfonamide compounds of formula I wherein W is a C 1-5 branched or unbranched alkyl group or a C 2-5 alkenyl group; n is 0 or 1; R 1 is H, a C 1-8 branched or unbranched alkyl group, a C 2-8 alkenyl group, or an aryl or aralkyl group; Ar 1 is a substituted thienyl, furyl, pyrrolyl, imidazothiazolyl, thiazolyl, pyridyl or phenyl group; and Ar 2 is a substituted phenyl, indolyl or benzoimidazolyl group; in the preparation of a medicament for treating proliferative disorders. Further aspects of the invention relate to compounds of formula I, pharmaceutical compositions thereof, and an assay for determining binding to HDM2.

  本发明涉及式 I 双芳磺酰胺化合物的用途 其中 W 是 C 1-5 支链或未支链烷基或 C 2-5 烯基；n 为 0 或 1； R 1 是 H、C 1-8 支链或未支链烷基、C 2-8 烯基、芳基或芳烷基； Ar 1 是取代的噻吩基、呋喃基、吡咯基、咪唑噻唑基、噻唑基、吡啶基或苯基；以及 Ar 2 是取代的苯基、吲哚基或苯并咪唑基；用于制备治疗增生性疾病的药物。本发明的其他方面涉及式 I 的化合物、其药物组合物以及确定与 HDM2 结合的检测方法。
• Design and synthesis of benzenesulfonanilides active against methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus
  作者：Kensuke Namba、Xiaoxia Zheng、Kazunori Motoshima、Hidetomo Kobayashi、Akihiro Tai、Eizo Takahashi、Kenji Sasaki、Keinosuke Okamoto、Hiroki Kakuta

  DOI：10.1016/j.bmc.2008.04.040

  日期：2008.6

  Vancomycin is mainly used as an antibacterial agent of last resort, but recently vancomycin-resistant bacterial strains have been emerging. Although new antimicrobials have been developed in order to overcome drug-resistant bacteria, many are structurally complex beta-lactams or quinolones. In this study, we aimed to create new anti-drug-resistance antibacterials which can be synthesized in a few steps from inexpensive starting materials. Since sulfa drugs function as p-aminobenzoic acid mimics and inhibit dihydropteroate synthase (DHPS) in the folate pathway, we hypothesized that sulfa derivatives would act as folate metabolite-mimics and inhibit bacterial folate metabolism. Screening of our sulfonanilide libraries, including benzenesulfonanilide-type cyclooxygenase-1-selective inhibitors, led us to discover benzenesulfonanilides with potent anti-methicillin-resistant Staphylococcus aureus (MRSA)/vancomycin-resistant Enterococcus (VRE) activity, that is, N-3,5-bis(trifluoromethyl) phenyl-3,5-dichlorobenzenesulfonanilide (16b) [MIC = 0.5 mu g/mL (MRSA), 1.0 mu g/mL (VRE)], and 3,5-bis(trifluoromethyl)-N-(3,5-dichlorophenyl) benzenesulfonanilide (16c) [MIC = 0.5 mu g/mL (MRSA), 1.0 mu g/mL (VRE)]. These compounds are more active than vancomycin [MIC = 2.0 mu g/mL (MRSA), 125 mu g/mL (VRE)], but do not possess an amino group, which is essential for DHPS inhibition by sulfa drugs. These results suggested that the mechanism of antibacterial action of compounds 16b and 16c is different from that of sulfa drugs. We also confirmed the activity of these compounds against clinical isolates of Gram-positive bacteria. (C) 2008 Elsevier Ltd. All rights reserved.
• Behnisch, Chemische Berichte, 1948, vol. 81, p. 297,302
  作者：Behnisch

  DOI：——

  日期：——
• BISARYLSULFONAMIDE COMPOUNDS AND THEIR USE IN CANCER THERAPY
  申请人：Cyclacel Limited

  公开号：EP1519932A1

  公开（公告）日：2005-04-06