4-[(4-methoxyphenyl)methylideneamino]benzenesulfonamide | 66667-56-9

• 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-methoxyphenyl)methylideneamino]benzenesulfonamide
• 英文别名: N⁴-(4-methoxybenzylidene) sulfanilamide；N-(4-methoxy-benzylidene)-sulfanilic acid amide；N-(4-Methoxy-benzyliden)-sulfanilsaeure-amid；N-(4-methoxybenzylidene)-4-sulfamoylaniline
• CAS: 66667-56-9
• 化学式: C₁₄H₁₄N₂O₃S
• 分子量: 290.343
• InChiKey: MLUHDVSELBSKPI-MHWRWJLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  81.75
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-[(4-methoxyphenyl)methylideneamino]benzenesulfonamide 在 1,4-二氧六环 、 镍 作用下， 生成 4-[(4-methoxybenzyl)amino]benzenesulfonamide
  参考文献：
  名称：

  Sulfanilamide Compounds. IV. N⁴-Aryl- and N⁴-Arylidine-N¹-substituted Sulfanilamides

  摘要：

  DOI：

  10.1021/ja01864a004
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 磺胺 以95%的产率得到4-[(4-methoxyphenyl)methylideneamino]benzenesulfonamide
  参考文献：
  名称：

  1,2-diphenylpyrrole derivatives, their preparation and their therapeutic

  摘要：

  化合物的化学式(I)和(II)：其中R为氢、卤素或烷基；R.sup.1为烷基、氨基或取代氨基；R.sup.2为可选择取代的苯基；R.sup.3为氢、卤素或可选择取代的烷基；R.sup.4为氢、可选择取代的烷基、环烷基、芳基或芳基烷基！具有宝贵的镇痛、抗炎、退热和抗过敏活性，并具有抑制白三烯产生和抑制骨吸收的能力。它们相对缺乏通常由于使用具有这些活性的化合物而产生的副作用。

  公开号：

  US05908858A1

文献信息

• Kamdar; Chavda; Parikh, Journal of the Indian Chemical Society, 1987, vol. 64, # 5, p. 298 - 301
  作者：Kamdar、Chavda、Parikh

  DOI：——

  日期：——
• Gray; Buttle; Stephenson, Biochemical Journal, 1937, vol. 31, p. 724,727
  作者：Gray、Buttle、Stephenson

  DOI：——

  日期：——
• 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.
• 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.
• 1,2-Diphenylpyrrole derivatives, their preparation and their therapeutic uses
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP0799823B1

  公开（公告）日：2007-10-31