4-[(4-nitrophenyl)methylideneamino]benzenesulfonamide | 66667-60-5

• 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: 4-[(4-nitrophenyl)methylideneamino]benzenesulfonamide
• 英文别名: N⁴-(4-nitrobenzylidene) sulfanilamide；N-(4-nitro-benzylidene)-sulfanilic acid amide；N-(4-Nitro-benzyliden)-sulfanilsaeure-amid
• CAS: 66667-60-5
• 化学式: C₁₃H₁₁N₃O₄S
• 分子量: 305.314
• InChiKey: IJEQJCKQAKELNC-OQLLNIDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115.66
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  对硝基苯甲醛 、 磺胺 反应 0.08h， 以30%的产率得到4-[(4-nitrophenyl)methylideneamino]benzenesulfonamide
  参考文献：
  名称：

  Selective COX-2 inhibitors. Part 2: Synthesis and biological evaluation of 4-benzylideneamino- and 4-phenyliminomethyl-benzenesulfonamides

  摘要：

  Two series of 4-benzylideneamino- and 4-phenyliminomethyl-benzenesulfonamide derivatives were designed and synthesized for the evaluation as selective cyclooxygenase-2 (COX-2) inhibitors in a cellular assay using human whole blood (HWB). Extensive structure-activity relationships (SAR) were studied within these series. Several compounds were found to be novel and selective COX-2 inhibitors. Among them, the most potent and selective was 4-(3-carboxy-4-hydroxy-benzylideneamino)benzenesulfonamide (20, LA2135), (IC50'S for COX- 1: 85.13 mu M; COX-2: 0.74 mu M; SI: 114.5), being more active COX-2 selective than celecoxib. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.033

文献信息

• Sulfanilamide Compounds. IV. N⁴-Aryl- and N⁴-Arylidine-N¹-substituted Sulfanilamides
  作者：H. G. Kolloff、James H. Hunter

  DOI：10.1021/ja01864a004

  日期：1940.7
• Carbonic anhydrase inhibitors. Part 35. Synthesis of Schiff bases derived from sulfanilamide and aromatic aldehydes: the first inhibitors with equally high affinity towards cytosolic and membrane-bound isozymes
  作者：CT Supuran、A Nicolae、A Popescu

  DOI：10.1016/0223-5234(96)85163-4

  日期：1996.1

  A series of Schiff bases was prepared by reaction of sulfanilamide with substituted benzene- and heterocyclic aldehydes. The compounds were characterized by standard procedures, and were assayed as inhibitors of the zinc enzyme carbonic anhydrase (CA). The new compounds act as inhibitors towards isozymes CA I and II (cytosolic) and CA IV (membrane-bound), and possess an equally high affinity for the last two, in contrast to classical inhibitors which are 17-33 times less effective against CA IV. This is the first evidence of high-affinity CA IV inhibitors, and might lead to the development of low molecular weight CA IV isozyme-specific derivatives.
• METHODS AND COMPOSITIONS OF TRAIL-DEATH RECEPTOR AGONISTS/ACTIVATORS
  申请人：Srivastava Rakesh K.

  公开号：US20080214547A1

  公开（公告）日：2008-09-04

  This invention describes a series of methods and compositions for prevention and treatment of diseases such as cancer. One aspect of the invention describes small molecule-based drugs that can be used to bind to death receptors TRAIL-R1/DR4 and/or TRAIL-R2/DR5 and induce apoptosis in cancer cells, while sparing normal cells. The invention also describes TRAIL Death Receptor Agonists/Activators (DRAs) and their uses, such as the induction of apoptosis through caspase-8 and caspase-3 activation. The present invention also describes the methods of treating cancers, such as breast, prostate, colon, pancreatic, ovarian, lung, and brain cancers, leukemia, lymphoma, multiple myeloma, and mesothelioma, using DRAs either as single-agent treatments, or in combination with other therapies.
• US7915245B2
  申请人：——

  公开号：US7915245B2

  公开（公告）日：2011-03-29
• Selective COX-2 inhibitors. Part 2: Synthesis and biological evaluation of 4-benzylideneamino- and 4-phenyliminomethyl-benzenesulfonamides
  作者：Shwu-Jiuan Lin、Wei-Jern Tsai、Wen-Fei Chiou、Tsang-Hsiung Yang、Li-Ming Yang

  DOI：10.1016/j.bmc.2007.11.033

  日期：2008.3

  Two series of 4-benzylideneamino- and 4-phenyliminomethyl-benzenesulfonamide derivatives were designed and synthesized for the evaluation as selective cyclooxygenase-2 (COX-2) inhibitors in a cellular assay using human whole blood (HWB). Extensive structure-activity relationships (SAR) were studied within these series. Several compounds were found to be novel and selective COX-2 inhibitors. Among them, the most potent and selective was 4-(3-carboxy-4-hydroxy-benzylideneamino)benzenesulfonamide (20, LA2135), (IC50'S for COX- 1: 85.13 mu M; COX-2: 0.74 mu M; SI: 114.5), being more active COX-2 selective than celecoxib. (C) 2007 Elsevier Ltd. All rights reserved.