3-(4-methylphenyl)-4-(4-sulfonamidophenyl)-2(5H)-furanone | 1349022-41-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-(4-methylphenyl)-4-(4-sulfonamidophenyl)-2(5H)-furanone
• 英文别名: 4-[4-(4-methylphenyl)-5-oxo-2H-furan-3-yl]benzenesulfonamide
• CAS: 1349022-41-8
• 化学式: C₁₇H₁₅NO₄S
• 分子量: 329.376
• InChiKey: DXIFWWUDOXUTQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  94.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-oxo-2-(4-sulfamoylphenyl)ethyl 2-(p-tolyl)acetate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 0.25h， 生成 3-(4-methylphenyl)-4-(4-sulfonamidophenyl)-2(5H)-furanone
  参考文献：
  名称：

  Structure–activity relationship of celecoxib and rofecoxib for the membrane permeabilizing activity

  摘要：

  Non-steroidal anti-inflammatory drugs (NSAIDs) achieve their anti-inflammatory effect by inhibiting cyclooxygenase activity. We previously suggested that in addition to cyclooxygenase-inhibition at the gastric mucosa, NSAID-induced gastric mucosal cell death is required for the formation of NSAID-induced gastric lesions in vivo. We showed that celecoxib exhibited the most potent membrane permeabilizing activity among the NSAIDs tested. In contrast, we have found that the NSAID rofecoxib has very weak membrane permeabilizing activity. To understand the membrane permeabilizing activity of coxibs in terms of their structure-activity relationship, we separated the structures of celecoxib and rofecoxib into three parts, synthesized hybrid compounds by substitution of each of the parts, and examined the membrane permeabilizing activities of these hybrids. The results suggest that the sulfonamidophenyl subgroup of celecoxib or the methanesulfonylphenyl subgroup of rofecoxib is important for their potent or weak membrane permeabilizing activity, respectively. These findings provide important information for design and synthesis of new coxibs with lower membrane permeabilizing activity. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.02.032

文献信息

• Structure–activity relationship of celecoxib and rofecoxib for the membrane permeabilizing activity
  作者：Naoki Yamakawa、Koichiro Suzuki、Yasunobu Yamashita、Takashi Katsu、Kengo Hanaya、Mitsuru Shoji、Takeshi Sugai、Tohru Mizushima

  DOI：10.1016/j.bmc.2014.02.032

  日期：2014.4

  Non-steroidal anti-inflammatory drugs (NSAIDs) achieve their anti-inflammatory effect by inhibiting cyclooxygenase activity. We previously suggested that in addition to cyclooxygenase-inhibition at the gastric mucosa, NSAID-induced gastric mucosal cell death is required for the formation of NSAID-induced gastric lesions in vivo. We showed that celecoxib exhibited the most potent membrane permeabilizing activity among the NSAIDs tested. In contrast, we have found that the NSAID rofecoxib has very weak membrane permeabilizing activity. To understand the membrane permeabilizing activity of coxibs in terms of their structure-activity relationship, we separated the structures of celecoxib and rofecoxib into three parts, synthesized hybrid compounds by substitution of each of the parts, and examined the membrane permeabilizing activities of these hybrids. The results suggest that the sulfonamidophenyl subgroup of celecoxib or the methanesulfonylphenyl subgroup of rofecoxib is important for their potent or weak membrane permeabilizing activity, respectively. These findings provide important information for design and synthesis of new coxibs with lower membrane permeabilizing activity. (C) 2014 Published by Elsevier Ltd.