{butyl[4-(4-oxopiperidin-1-yl)phenyl]sulfamoyl}acetic acid benzyl ester | 373360-07-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: {butyl[4-(4-oxopiperidin-1-yl)phenyl]sulfamoyl}acetic acid benzyl ester
• 英文别名: Benzyl 2-[butyl-[4-(4-oxopiperidin-1-yl)phenyl]sulfamoyl]acetate；benzyl 2-[butyl-[4-(4-oxopiperidin-1-yl)phenyl]sulfamoyl]acetate
• CAS: 373360-07-7
• 化学式: C₂₄H₃₀N₂O₅S
• 分子量: 458.579
• InChiKey: YATMXWKSYRZIJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[5-((1R)-2-amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide 、 {butyl[4-(4-oxopiperidin-1-yl)phenyl]sulfamoyl}acetic acid benzyl ester 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以35%的产率得到benzyl [(butyl-4-{4-[((2R)-2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidinyl}anilino)sulfonyl]acetate
  参考文献：
  名称：

  Novel (4-Piperidin-1-yl)-phenyl Sulfonamides as Potent and Selective Human β3 Agonists

  摘要：

  A series of novel (4-piperidin-1-yl)-phenyl sulfonamides was prepared and evaluated for their biological activity on the human beta (3)-adrenergic receptor (AR). Replacement of the 3,4-dihydroxyl group of the catechol moiety with 4-hydroxyl-3-methyl sulfonamide on the left-hand side of the compounds resulted in a number of potent full agonists at the beta (3) receptor. Modification of the right-hand side of the compounds by incorporation of a free carboxylic acid resulted in a few potent human beta (3) agonists with low affinities for beta (1)- and beta (2)-ARs. N-Alkyl substitution on the 4-piperidin-1-yl-phenylamine further increased the beta (3) potency while maintaining the selectivity. For example, sulfonamide 48 is a potent full beta (3) agonist (EC50 = 0.004 muM, IA = 1.0) with > 500-fold selectivity over beta (1)- and beta (2)-ARs. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00114-6
• 作为产物：
  描述：

  8-(4-硝基苯基)-1,4-二氧杂-8-氮杂螺[4.5]癸烷 在 palladium on activated charcoal 盐酸 、 高氯酸 、 氢气 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、206.84 kPa 条件下， 反应 93.0h， 生成 {butyl[4-(4-oxopiperidin-1-yl)phenyl]sulfamoyl}acetic acid benzyl ester
  参考文献：
  名称：

  Novel (4-Piperidin-1-yl)-phenyl Sulfonamides as Potent and Selective Human β3 Agonists

  摘要：

  A series of novel (4-piperidin-1-yl)-phenyl sulfonamides was prepared and evaluated for their biological activity on the human beta (3)-adrenergic receptor (AR). Replacement of the 3,4-dihydroxyl group of the catechol moiety with 4-hydroxyl-3-methyl sulfonamide on the left-hand side of the compounds resulted in a number of potent full agonists at the beta (3) receptor. Modification of the right-hand side of the compounds by incorporation of a free carboxylic acid resulted in a few potent human beta (3) agonists with low affinities for beta (1)- and beta (2)-ARs. N-Alkyl substitution on the 4-piperidin-1-yl-phenylamine further increased the beta (3) potency while maintaining the selectivity. For example, sulfonamide 48 is a potent full beta (3) agonist (EC50 = 0.004 muM, IA = 1.0) with > 500-fold selectivity over beta (1)- and beta (2)-ARs. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00114-6