4-[(4-oxocyclohexa-2,5-dien-1-ylidene)methylamino]benzenesulfonamide | 66667-58-1

• 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-oxocyclohexa-2,5-dien-1-ylidene)methylamino]benzenesulfonamide
• 英文别名: N⁴-(4-hydroxybenzylidene) sulfanilamide；N-(4-hydroxy-benzylidene)-sulfanilic acid amide；N-(4-Hydroxy-benzyliden)-sulfanilsaeure-amid
• CAS: 66667-58-1
• 化学式: C₁₃H₁₂N₂O₃S
• 分子量: 276.316
• InChiKey: QEZYWFVOEUVTBF-OQLLNIDSSA-N

物化性质

• 沸点：
  532.4±60.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.75
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-[(4-oxocyclohexa-2,5-dien-1-ylidene)methylamino]benzenesulfonamide 在 1,4-二氧六环 、 镍 作用下， 生成 N-(4-hydroxy-benzyl)-sulfanilic acid amide
  参考文献：
  名称：

  Preparation of p-(benzylamino) benzenesulphonamides

  摘要：

  公开号：

  US02111768A1
• 作为产物：
  描述：

  对羟基苯甲醛 、 磺胺 反应 0.08h， 以40%的产率得到4-[(4-oxocyclohexa-2,5-dien-1-ylidene)methylamino]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

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

  DOI：——

  日期：——
• 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.
• CHAUHAN, NATUBHAI A., J. INST. CHEM. (INDIA), 62,(1990) N, C. 71-72
  作者：CHAUHAN, NATUBHAI A.

  DOI：——

  日期：——
• KAMDAR, G. C.;CHAVDA, A. C.;PARIKH, A. R., J. INDIAN CHEM. SOC., 64,(1987) N 5, 298-301
  作者：KAMDAR, G. C.、CHAVDA, A. C.、PARIKH, A. R.

  DOI：——

  日期：——