7-[4-(2,4-dichlorophenyl)aminosulphonyl]-6-hydroxy-4-methoxybenzofuran-5-carboxylic acid | 1248345-45-0

• 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: 7-[4-(2,4-dichlorophenyl)aminosulphonyl]-6-hydroxy-4-methoxybenzofuran-5-carboxylic acid
• 英文别名: 7-[(2,4-Dichlorophenyl)sulfamoyl]-6-hydroxy-4-methoxy-1-benzofuran-5-carboxylic acid
• CAS: 1248345-45-0
• 化学式: C₁₆H₁₁Cl₂NO₇S
• 分子量: 432.238
• InChiKey: DTNLKCKCWGLGOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  7-(chlorosulphonyl)-6-hydroxy-4-methoxybenzofuran-5-carboxylic acid 、 2,4-二氯苯胺 在 吡啶 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以65%的产率得到7-[4-(2,4-dichlorophenyl)aminosulphonyl]-6-hydroxy-4-methoxybenzofuran-5-carboxylic acid
  参考文献：
  名称：

  Design, synthesis and anti-ulcerogenic effect of some of furo-salicylic acid derivatives on acetic acid-induced ulcerative colitis

  摘要：

  Ulcerative colitis is a chronically recurrent inflammatory bowel disease of unknown origin. The present work describes design and synthesis of 3-aminofurosalicylic acid 4, azo-conjugates with aniline 2a, 4-ASA 2b or sulphapyridine 2c as well as N-arylsulphonamido 5, chlorosulphonyl 6, aminosulphonyl 7 and N-arylaminosulphonyl derivatives 8 (positional isosters of 5). All the synthesized compounds were evaluated for their anti-ulcerogenic effect on acetic acid-induced ulcerative colitis in rats. It was noticed that oral treatment with sulphasalazine (a reference drug) and the tested compounds 2a, 2c, 4 and 5c in equimolar doses significantly reduced the intensity of lesion score, ulcer area, ulcer index and wet weight/length ratio compared to the control group. On the other hand, compounds 2b, 5a, 5b and 7 had a lower anti-ulcerogenic efficacy. Also, the antimicrobial activity of the synthesized compounds was screened in vitro using the agar diffusion assay technique. In addition, docking of the tested compounds into cycloxygenase II using molecular operating environment (MOE) was performed in order to rationalize the obtained biological results and their mechanism of action. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.071

文献信息

• Design, synthesis and anti-ulcerogenic effect of some of furo-salicylic acid derivatives on acetic acid-induced ulcerative colitis
  作者：Ghaneya S. Hassan、Gamal A. Soliman

  DOI：10.1016/j.ejmech.2010.05.071

  日期：2010.9

  Ulcerative colitis is a chronically recurrent inflammatory bowel disease of unknown origin. The present work describes design and synthesis of 3-aminofurosalicylic acid 4, azo-conjugates with aniline 2a, 4-ASA 2b or sulphapyridine 2c as well as N-arylsulphonamido 5, chlorosulphonyl 6, aminosulphonyl 7 and N-arylaminosulphonyl derivatives 8 (positional isosters of 5). All the synthesized compounds were evaluated for their anti-ulcerogenic effect on acetic acid-induced ulcerative colitis in rats. It was noticed that oral treatment with sulphasalazine (a reference drug) and the tested compounds 2a, 2c, 4 and 5c in equimolar doses significantly reduced the intensity of lesion score, ulcer area, ulcer index and wet weight/length ratio compared to the control group. On the other hand, compounds 2b, 5a, 5b and 7 had a lower anti-ulcerogenic efficacy. Also, the antimicrobial activity of the synthesized compounds was screened in vitro using the agar diffusion assay technique. In addition, docking of the tested compounds into cycloxygenase II using molecular operating environment (MOE) was performed in order to rationalize the obtained biological results and their mechanism of action. (C) 2010 Elsevier Masson SAS. All rights reserved.