N-{4-[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)phenylsulfamoyl]phenyl}acetamide | 373359-52-5

• 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: N-{4-[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)phenylsulfamoyl]phenyl}acetamide
• 英文别名: N-{4-[4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-phenylsulfamoyl]-phenyl}-acetamide；N-[4-[[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)phenyl]sulfamoyl]phenyl]acetamide
• CAS: 373359-52-5
• 化学式: C₂₁H₂₅N₃O₅S
• 分子量: 431.513
• InChiKey: PBNXEQNIEKFBSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-{4-[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)phenylsulfamoyl]phenyl}acetamide 在 盐酸 作用下， 以61%的产率得到N-{4-[4-(4-oxopiperidin-1-yl)phenylsulfamoyl]phenyl}acetamide
  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 氢气 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、206.84 kPa 条件下， 反应 19.0h， 生成 N-{4-[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)phenylsulfamoyl]phenyl}acetamide
  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

文献信息

• Cyclic amine phenyl beta-3 adrenergic receptor agonists
  申请人：——

  公开号：US20020028835A1

  公开（公告）日：2002-03-07

  This invention provides compounds of Formula I having the structure 1 wherein, R 1 , R 2 , R 3 , R 4 , R 5 , T, T 1 , T 2 , and X are as defined hereinbefore, or a pharmaceutically acceptable salt thereof, which are useful in treating or inhibiting metabolic disorders related to insulin resistance or hyperglycemia (typically associated with obesity or glucose intolerance), atherosclerosis, gastrointestinal disorders, neurogenetic inflammation, glaucoma, ocular hypertension and frequent urination; and are particularly useful in the treatment or inhibition of type II diabetes.

  本发明提供了具有结构1的化合物，其中R1、R2、R3、R4、R5、T、T1、T2和X如前所定义，或其药学上可接受的盐，其在治疗或抑制与胰岛素抵抗或高血糖有关的代谢紊乱（通常与肥胖或葡萄糖不耐症有关）、动脉粥样硬化、胃肠道疾病、神经遗传性炎症、青光眼、眼压增高和频繁排尿方面非常有用；尤其适用于治疗或抑制2型糖尿病。
• CYCLIC AMINE PHENYL BETA-3 ADRENERGIC RECEPTOR AGONISTS
  申请人：Wyeth

  公开号：EP1301482A1

  公开（公告）日：2003-04-16
• US6525202B2
  申请人：——

  公开号：US6525202B2

  公开（公告）日：2003-02-25
• US7022716B2
  申请人：——

  公开号：US7022716B2

  公开（公告）日：2006-04-04
• [EN] CYCLIC AMINE PHENYL BETA-3 ADRENERGIC RECEPTOR AGONISTS<br/>[FR] AGONISTES DU RECEPTEUR BETA-3 ADRENERGIQUE D'AMINEPHENYLE CYCLIQUE
  申请人：AMERICAN HOME PROD

  公开号：WO2002006232A1

  公开（公告）日：2002-01-24

  This invention provides compounds of Formula (I) wherein: R?1, R2, R3, R4, R5, T, T1, T2¿, and X are as defined hereinbefore, or a pharmaceutically acceptable salt thereof, which are useful in treating or inhibiting metabolic disorders related to insulin resistance or hyperglycemia (typically associated with obesity or glucose intolerance), atherosclerosis, gastrointestinal disorders, neurogenetic inflammation, glaucoma, ocular hypertension and frequent urination; and are particularly useful in the treatment or inhibition of type II diabetes.