2-(3-nitrophenyl)ethanesulfonic acid amide | 402508-79-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3-nitrophenyl)ethanesulfonic acid amide
• 英文别名: 2-(3-nitrophenyl)ethanesulfonamide
• CAS: 402508-79-6
• 化学式: C₈H₁₀N₂O₄S
• 分子量: 230.244
• InChiKey: OFRUFASAYQBJAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3-nitrophenyl)ethanesulfonic acid amide 在 10percent Pd/C 盐酸 、 氢气 、 sodium cyanoborohydride 、 溶剂黄146 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 98.0h， 生成 2-{3-[((2R)-2-{[(2R)-2-hydroxy-2-(3-chlorophenyl)ethyl]amino}propyl)amino]phenyl}-N-(phenylsulfonyl)ethanesulfonamide
  参考文献：
  名称：

  Synthesis and Evaluation of Potent and Selective β₃ Adrenergic Receptor Agonists Containing Acylsulfonamide, Sulfonylsulfonamide, and Sulfonylurea Carboxylic Acid Isosteres

  摘要：

  Starting from phenethanolamine aniline leads 3a and 3b, we have identified a series of functionally potent and selective beta(3) adrenergic receptor (AR) agonists containing acylsulfonamide, sulfonylsulfonamide, or sulfonylurea groups within the aniline phenethanolamine series. In beta(3) beta(2), and beta(1) AR cAMP functional assays, 3a and other right-hand side (RHS) carboxylate analogues were found to be full agonists that were modestly selective against beta(1) or beta(2) ARs, while analogues lacking RHS acid functionality were active at beta(3) AR but not selective. Replacement of the carboxylate with acylthiazole and acylmethylsulfone gave potent, but only modestly selective, compounds. Increasing the size of the RHS sulfonamide substituent with phenyl or p-toluene afforded compounds with good potency and functional selectivity (beta(3) AR pEC(50) greater than 8; beta(1) and beta(2) AR selectivity greater than 40- and 500-fold, respectively). Our SAR studies suggest that the potency and selectivity profile of the best analogues reported here is a result of both the steric bulk and acidity of the RHS sulfonamide NH group. Although all of the analogues had a pharmacokinetic half-life of less than 2 h, acylsulfonamides 43 and 44 did show moderately low clearance in dogs. These two compounds were further evaluated by thermographic imaging in mice and were found to produce a robust thermogenic response via oral administration.

  DOI：

  10.1021/jm0101500
• 作为产物：
  描述：

  2-(3-nitrophenyl)ethanesulfonic acid 在 氯化亚砜 、 氨 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 2-(3-nitrophenyl)ethanesulfonic acid amide
  参考文献：
  名称：

  Synthesis and Evaluation of Potent and Selective β₃ Adrenergic Receptor Agonists Containing Acylsulfonamide, Sulfonylsulfonamide, and Sulfonylurea Carboxylic Acid Isosteres

  摘要：

  Starting from phenethanolamine aniline leads 3a and 3b, we have identified a series of functionally potent and selective beta(3) adrenergic receptor (AR) agonists containing acylsulfonamide, sulfonylsulfonamide, or sulfonylurea groups within the aniline phenethanolamine series. In beta(3) beta(2), and beta(1) AR cAMP functional assays, 3a and other right-hand side (RHS) carboxylate analogues were found to be full agonists that were modestly selective against beta(1) or beta(2) ARs, while analogues lacking RHS acid functionality were active at beta(3) AR but not selective. Replacement of the carboxylate with acylthiazole and acylmethylsulfone gave potent, but only modestly selective, compounds. Increasing the size of the RHS sulfonamide substituent with phenyl or p-toluene afforded compounds with good potency and functional selectivity (beta(3) AR pEC(50) greater than 8; beta(1) and beta(2) AR selectivity greater than 40- and 500-fold, respectively). Our SAR studies suggest that the potency and selectivity profile of the best analogues reported here is a result of both the steric bulk and acidity of the RHS sulfonamide NH group. Although all of the analogues had a pharmacokinetic half-life of less than 2 h, acylsulfonamides 43 and 44 did show moderately low clearance in dogs. These two compounds were further evaluated by thermographic imaging in mice and were found to produce a robust thermogenic response via oral administration.

  DOI：

  10.1021/jm0101500

文献信息

• [EN] THIAZOLE AND OXAZOLE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASE À BASE DE THIAZOLE ET D'OXAZOLE
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2009076140A1

  公开（公告）日：2009-06-18

  The present invention provides thiazole and oxazole compounds, compositions containing the same, as well as processes for the preparation and methods for their use as pharmaceutical agents.

  本发明提供了噻唑和恶唑化合物、含有该化合物的组合物，以及它们的制备方法和作为药物的应用方法。
• [EN] PHARMACEUTICALLY ACTIVE DISUBSTITUTED TRIAZINE DERIVATIVES<br/>[FR] DÉRIVÉS DE TRIAZINE DISUBSTITUÉS PHARMACEUTIQUEMENT ACTIFS
  申请人：LEAD DISCOVERY CENTER GMBH

  公开号：WO2011116951A1

  公开（公告）日：2011-09-29

  The present invention relates to disubstituted triazine derivatives and/or pharmaceutically acceptable salts thereof, the use of these derivatives as pharmaceutically active agents, especially for the prophylaxis and/or treatment of infectious diseases, including opportunistic diseases, immunological diseases, autoimmune diseases, cardiovascular diseases, cell proliferative diseases, inflammation, erectile dysfunction and stroke, and pharmaceutical compositions containing at least one of said disubstituted triazine derivatives and/or pharmaceutically acceptable salts thereof. Furthermore, the present invention relates to the use of said disubstituted triazine derivatives as inhibitors for a protein kinase. formula (I) wherein R1 is formula (II), formula (III) or formula (IV).

  本发明涉及二取代三嗪衍生物和/或其药用盐，这些衍生物作为药用活性剂的用途，特别是用于预防和/或治疗传染性疾病，包括机会性疾病、免疫性疾病、自身免疫疾病、心血管疾病、细胞增殖性疾病、炎症、勃起功能障碍和中风，以及含有至少一个该二取代三嗪衍生物和/或其药用盐的药物组合物。此外，本发明涉及所述二取代三嗪衍生物作为蛋白激酶抑制剂的用途。其中，R1为公式(II)、公式(III)或公式(IV)。
• [EN] PHARMACEUTICALLY ACTIVE DISUBSTITUTED PYRIDINE DERIVATIVES<br/>[FR] DÉRIVÉS DE PYRIDINE DISUBSTITUÉS PHARMACEUTIQUEMENT ACTIFS
  申请人：LEAD DISCOVERY CENTER GMBH

  公开号：WO2012117059A1

  公开（公告）日：2012-09-07

  The present invention relates to disubstituted pyridine derivatives and/or pharmaceutically acceptable salts thereof, the use of these derivatives as pharmaceutically active agents, especially for the prophylaxis and/or treatment of infectious diseases, including opportunistic diseases, immunological diseases, autoimmune diseases, cardiovascular diseases, cell proliferative diseases, inflammation, erectile dysfunction and stroke, and pharmaceutical compositions containing at least one of said disubstituted pyridine derivatives and/or pharmaceutically acceptable salts thereof. Furthermore, the present invention relates to the use of said disubstituted pyridine derivatives as inhibitors for a protein kinase.

  本发明涉及二取代吡啶衍生物和/或其药学上可接受的盐，这些衍生物作为药理活性剂的使用，特别是用于预防和/或治疗传染病，包括机会性疾病、免疫疾病、自身免疫疾病、心血管疾病、细胞增殖性疾病、炎症、勃起功能障碍和中风，以及含有至少一种所述二取代吡啶衍生物和/或其药学上可接受的盐的制药组合物。此外，本发明还涉及使用所述二取代吡啶衍生物作为蛋白激酶抑制剂。
• Thiazole And Oxazole Kinase Inhibitors
  申请人：Adjabeng George

  公开号：US20110098296A1

  公开（公告）日：2011-04-28

  The present invention provides thiazole and oxazole compounds, compositions containing the same, as well as processes for the preparation and methods for their use as pharmaceutical agents.

  本发明提供了噻唑和异噁唑化合物，包含它们的组合物，以及制备它们的方法和用作药物的方法。
• PHARMACEUTICALLY ACTIVE DISUBSTITUTED TRIAZINE DERIVATIVES
  申请人：Eickhoff Jan

  公开号：US20130079345A1

  公开（公告）日：2013-03-28

  The present invention relates to disubstituted triazine derivatives and/or pharmaceutically acceptable salts thereof, the use of these derivatives as pharmaceutically active agents, especially for the prophylaxis and/or treatment of infectious diseases, including opportunistic diseases, immunological diseases, autoimmune diseases, cardiovascular diseases, cell proliferative diseases, inflammation, erectile dysfunction and stroke, and pharmaceutical compositions containing at least one of said disubstituted triazine derivatives and/or pharmaceutically acceptable salts thereof. Furthermore, the present invention relates to the use of said disubstituted triazine derivatives as inhibitors for a protein kinase.

  本发明涉及二取代三嗪衍生物和/或其药学上可接受的盐，这些衍生物作为药物活性剂的使用，特别是用于预防和/或治疗传染病，包括机会性疾病、免疫疾病、自身免疫性疾病、心血管疾病、细胞增殖性疾病、炎症、勃起功能障碍和中风，以及至少包含其中一种二取代三嗪衍生物和/或其药学上可接受的盐的制药组合物。此外，本发明涉及使用所述二取代三嗪衍生物作为蛋白激酶抑制剂的用途。