5-[[[5-(Dimethylamino)-1-naphthalenyl]sulfonyl]amino]-3-methyl-4-isoxazolecarboxylic acid, ethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-[[[5-(Dimethylamino)-1-naphthalenyl]sulfonyl]amino]-3-methyl-4-isoxazolecarboxylic acid, ethyl ester
• 英文别名: 5-[[[5-(Dimethylamino)-1-naphthalenyl]sulfonyl]amino]-3-methyl-4-isoxazolecarboxylic acid,ethyl ester；5-(5-Dimethylamino-naphthalene-1-sulfonylamino)-3-methyl-isoxazole-4-carboxylic acid ethyl ester；ethyl 5-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]-3-methyl-1,2-oxazole-4-carboxylate
• 化学式: C₁₉H₂₁N₃O₅S
• 分子量: 403.459
• InChiKey: IENNCXYZSDIKGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  乙醛肟 、 丹酰胺 、 3-溴丙酸乙酯 在 sodium hypochlorite 、 caesium carbonate 作用下， 生成 5-[[[5-(Dimethylamino)-1-naphthalenyl]sulfonyl]amino]-3-methyl-4-isoxazolecarboxylic acid, ethyl ester
  参考文献：
  名称：

  Discovery and Structure-Activity Relationships of Sulfonamide ETA-Selective Antagonists

  摘要：

  Random screening of compounds in an ETA receptor binding assay led to the discovery of a class of benzenesulfonamide ligands. Optimization led to the development of 5-amino-N-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulfonamides which were functional antagonists. Structural features which were important to activity included a 1,5-substitution pattern on the naphthalene ring; a sulfonamide NH with a pK value < 7; an amine, preferably with alkyl substituents, at the 5-position; and methyl groups on both the 3- and 4-positions of the isoxazole.

  DOI：

  10.1021/jm00008a013

文献信息

• Discovery and Structure-Activity Relationships of Sulfonamide ETA-Selective Antagonists
  作者：Philip D. Stein、David M. Floyd、Sharon Bisaha、Joyce Dickey、Ravindar N. Girotra、Jack Z. Gougoutas、Michael Kozlowski、Ving G. Lee、Eddie C.-K. Liu

  DOI：10.1021/jm00008a013

  日期：1995.4

  Random screening of compounds in an ETA receptor binding assay led to the discovery of a class of benzenesulfonamide ligands. Optimization led to the development of 5-amino-N-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulfonamides which were functional antagonists. Structural features which were important to activity included a 1,5-substitution pattern on the naphthalene ring; a sulfonamide NH with a pK value < 7; an amine, preferably with alkyl substituents, at the 5-position; and methyl groups on both the 3- and 4-positions of the isoxazole.