NSC 56605-K | 404-02-4

• 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: NSC 56605-K
• 英文别名: sulfanilic acid-(3,5-bis-trifluoromethyl-anilide)；Sulfanilsaeure-(3,5-bis-trifluormethyl-anilid)；4-Amino-N-[3,5-bis(trifluoromethyl)phenyl]benzenesulfonamide
• CAS: 404-02-4
• 化学式: C₁₄H₁₀F₆N₂O₂S
• 分子量: 384.302
• InChiKey: QSCNYGSDOCABMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 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：
  80.6
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  NSC 56605-K 、 甲基磺酰氯 在 吡啶 作用下， 以53%的产率得到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 在 sodium hydroxide 、 sodium acetate 、 丙酮 作用下， 生成 NSC 56605-K
  参考文献：
  名称：

  Behnisch, Chemische Berichte, 1948, vol. 81, p. 297,302

  摘要：

  DOI：

文献信息

• 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.
• Synthetic Antimalarials. The Preparation of Certain Derivatives of Sulfanilamide¹
  作者：Nathan L. Drake、Charles M. Eaker、John A. Garman、Kenneth E. Hamlin、Robert A. Hayes、Stuart T. Haywood、Richard M. Peck、Robert K. Preston、John Sterling、John O. van Hook、Edward Walton

  DOI：10.1021/ja01212a070

  日期：1946.8
• Behnisch, Chemische Berichte, 1948, vol. 81, p. 297,302
  作者：Behnisch

  DOI：——

  日期：——
• DE734565
  申请人：——

  公开号：——

  公开（公告）日：——
• Benzene sulphonic acid derivatives and manufacture thereof
  申请人：WINTHROP CHEM CO INC

  公开号：US02248911A1

  公开（公告）日：1941-07-08