N-(4-(trifluoromethyl)phenyl)-3,5-dichlorobenzenesulfonamide

• 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-(4-(trifluoromethyl)phenyl)-3,5-dichlorobenzenesulfonamide
• 英文别名: 3,5-dichloro-N-(4-trifluoromethylphenyl)benzenesulfonamide；N-[4-(Trifluoromethyl)phenyl]-3,5-dichlorobenzenesulfonamide；3,5-dichloro-N-[4-(trifluoromethyl)phenyl]benzenesulfonamide
• 化学式: C₁₃H₈Cl₂F₃NO₂S
• 分子量: 370.179
• InChiKey: KGDSXEMDPHAXEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-(trifluoromethyl)phenyl)-3,5-dichlorobenzenesulfonamide 、 3-溴丙炔 在 sodium chloride 作用下， 以 N-甲基乙酰胺 、 水 、 苯 为溶剂， 以85.4%的产率得到N-propargyl-3,5-dichloro-N-(4-trifluoromethylphenyl)benzenesulfonamide
  参考文献：
  名称：

  EP778267

  摘要：

  公开号：
• 作为产物：
  描述：

  3,5-dichlorophenyl benzenesulfonyl chloride 、 对三氟甲基苯胺 在 吡啶 、 盐酸 、 sodium chloride 、 碳酸氢钠 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 以85.8%的产率得到N-(4-(trifluoromethyl)phenyl)-3,5-dichlorobenzenesulfonamide
  参考文献：
  名称：

  EP778267

  摘要：

  公开号：

文献信息

• SULFONAMIDE DERIVATIVES AND INSECTICIDE, MITICIDE AND NEMATICIDE CONTAINING THE SAME
  申请人：OTSUKA KAGAKU KABUSHIKI KAISHA

  公开号：EP0778267A1

  公开（公告）日：1997-06-11

  An object of the present invention is to provide a sulfonamide derivative which is useful as insecticidal, miticidal and nematocidal agents. The sulfonamide derivative of the invention is represented by the formula wherein R1 and R2 are the same or different and each represents a hydrogen atom, a lower haloalkyl group or a halogen atom, R3 is an ethynyl group, a cyano group, a lower alkoxy group, or a lower alkoxycarbonyl group, X and Y are the same or different and each represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a phenoxy group optionally having a substituent(s), a phenyl group optionally having a substituent(s), a pyridyloxy group optionally having a substituent(s), a cyano group, a nitro group, a lower alkylthio group or a lower alkyl sulfonyl group, and m and n are each an integer of 1 to 3.

  本发明的目的是提供一种可用作杀虫剂、杀螨剂和杀线虫剂的磺酰胺衍生物。本发明的磺酰胺衍生物由式表示 其中 R1 和 R2 相同或不同，各自代表氢原子、低级卤代烷基或卤素原子；R3 是乙炔基、氰基、低级烷氧基或低级烷氧羰基；X 和 Y 相同或不同，各自代表氢原子、卤素原子、低级烷基、低级烷氧基低级卤代烷基、低级卤代烷氧基、任选具有取代基的苯氧基、任选具有取代基的苯基、任选具有取代基的吡啶氧基、氰基、硝基、低级烷硫基或低级烷基磺酰基，且 m 和 n 均为 1 至 3 的整数。
• 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.
• Cu(OAc)₂-Catalyzed<i>N</i>-Arylation of Sulfonamides with Arylboronic Acids or Trimethoxy(phenyl)silane
  作者：Changduo Pan、Jiang Cheng、Huayue Wu、Jinchang Ding、Miaochang Liu

  DOI：10.1080/00397910802638495

  日期：2009.5.22

  Cu(OAc)2-catalyzed C-N bond-formation reaction of sulfonamides with organoboronic acids or trimethoxy(phenyl)silane was achieved in the presence of 20mol% of Cu(OAc)2, providing N-arylation products with yields ranging from moderate to good.
• EP778267
  申请人：——

  公开号：——

  公开（公告）日：——