N-(3-hydroxy-2-naphthyl)-N-isobutyl-5-methylfuran-2-sulfonamide | 916913-54-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(3-hydroxy-2-naphthyl)-N-isobutyl-5-methylfuran-2-sulfonamide
• CAS: 916913-54-7
• 化学式: C₁₉H₂₁NO₄S
• 分子量: 359.446
• InChiKey: LRYYJSAJFZNNBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  70.75
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(3-hydroxy-2-naphthyl)-N-isobutyl-5-methylfuran-2-sulfonamide 在 sodium hydroxide 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 4-[3-[N-isobutyl-N-(5-methyl-2-furylsulfonyl)amino]-2-naphthyloxymethyl]benzoic acid
  参考文献：
  名称：

  Optimization of sulfonamide derivatives as highly selective EP1 receptor antagonists

  摘要：

  A series of 4-[(2-{isobutyl[(5-methyl-2-furyl)sulfonyl]amino}phenoxy)methyl]benzoic acids and 4-({2-[isobutyl(1,3-thiazol-2-ylsulfonyl)amino]phenoxy}methyl)benzoic acids were synthesized and evaluated for their EP receptor affinities and EP1 receptor antagonist activities. Further structural optimization was carried out to reduce inhibitory activity against hepatic cytochrome P450 isozymes, which could represent a harmful potential drug interaction. Selected compounds were also evaluated for their binding affinities to hTP, hDP, mFP, and hIP, and for their hEP1 receptor antagonist activities. The results of structure-activity relationship studies are also presented.

  DOI：

  10.1016/j.bmc.2006.08.001
• 作为产物：
  描述：

  5-甲基呋喃-2-磺酰氯 在 吡啶 、 四丁基氟化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 N-(3-hydroxy-2-naphthyl)-N-isobutyl-5-methylfuran-2-sulfonamide
  参考文献：
  名称：

  Optimization of sulfonamide derivatives as highly selective EP1 receptor antagonists

  摘要：

  A series of 4-[(2-{isobutyl[(5-methyl-2-furyl)sulfonyl]amino}phenoxy)methyl]benzoic acids and 4-({2-[isobutyl(1,3-thiazol-2-ylsulfonyl)amino]phenoxy}methyl)benzoic acids were synthesized and evaluated for their EP receptor affinities and EP1 receptor antagonist activities. Further structural optimization was carried out to reduce inhibitory activity against hepatic cytochrome P450 isozymes, which could represent a harmful potential drug interaction. Selected compounds were also evaluated for their binding affinities to hTP, hDP, mFP, and hIP, and for their hEP1 receptor antagonist activities. The results of structure-activity relationship studies are also presented.

  DOI：

  10.1016/j.bmc.2006.08.001