4-(N,N-dibenzylsulfamoyl)benzoic acid | 102479-27-6

• 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: 4-(N,N-dibenzylsulfamoyl)benzoic acid
• 英文别名: 4-(dibenzylsulfamoyl)benzoic acid；4-dibenzylsulfamoyl-benzoic acid；4-Dibenzylsulfamoyl-benzoesaeure
• CAS: 102479-27-6
• 化学式: C₂₁H₁₉NO₄S
• 分子量: 381.452
• InChiKey: AYAKDXHPTOEADO-UHFFFAOYSA-N

物化性质

• 溶解度：
  19.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.095
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(N,N-dibenzylsulfamoyl)benzoic acid 在 氯化亚砜 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 N,N-dibenzyl-4-[2-(4-fluorophenyl)acetyl]benzenesulfonamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2-Phenylpyran-4-ones:  A New Class of Orally Active Cyclooxygenase-2 Inhibitors

  摘要：

  A series of 2-phenylpyran-4-ones were prepared and evaluated for their ability to inhibit cyclooxygenase-2 (COX-2). Extensive structure-activity relationship work was carried out within this series, and a number of potent and selective COX-2 inhibitors were identified. Compounds having a p-methylsulfone group at the 2-phenyl ring showed the best COX-2 inhibitory activity. The introduction of a substituted phenoxy ring at position 3 enhanced both the in vitro and in vivo activity within the series. A selected group of 3-phenoxypyran-4-ones exhibited excellent activity in an experimental model of pyresis. The in vivo antiinflammatory activity of these compounds was confirmed with the evaluation of their antiarthritic and analgesic effectiveness. Moreover, their pharmacokinetic profile in rats is compatible with a once a day administration by oral route in humans. Within this novel series, compounds 21, 31, 34, and 35 have been selected for further preclinical. and clinical evaluation.

  DOI：

  10.1021/jm049882t
• 作为产物：
  描述：

  对羧基苯磺酰胺 在 盐酸 、 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 6.0h， 生成 4-(N,N-dibenzylsulfamoyl)benzoic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2-Phenylpyran-4-ones:  A New Class of Orally Active Cyclooxygenase-2 Inhibitors

  摘要：

  A series of 2-phenylpyran-4-ones were prepared and evaluated for their ability to inhibit cyclooxygenase-2 (COX-2). Extensive structure-activity relationship work was carried out within this series, and a number of potent and selective COX-2 inhibitors were identified. Compounds having a p-methylsulfone group at the 2-phenyl ring showed the best COX-2 inhibitory activity. The introduction of a substituted phenoxy ring at position 3 enhanced both the in vitro and in vivo activity within the series. A selected group of 3-phenoxypyran-4-ones exhibited excellent activity in an experimental model of pyresis. The in vivo antiinflammatory activity of these compounds was confirmed with the evaluation of their antiarthritic and analgesic effectiveness. Moreover, their pharmacokinetic profile in rats is compatible with a once a day administration by oral route in humans. Within this novel series, compounds 21, 31, 34, and 35 have been selected for further preclinical. and clinical evaluation.

  DOI：

  10.1021/jm049882t

文献信息

• Identification of human T2R receptors that respond to bitter compounds that elicit the bitter taste in compositions, and the use thereof in assays to identify compounds that inhibit (block) bitter taste in composition and use thereof
  申请人：Li Xiaodong

  公开号：US20090274632A1

  公开（公告）日：2009-11-05

  The present invention relates to the discovery that specific human taste receptors in the T2R taste receptor family respond to particular bitter compounds present in, e.g., coffee. Also, the invention relates to the discovery of specific compounds and compositions containing that function as bitter taste blockers and the use thereof as bitter taste blockers or flavor modulators in, e.g., coffee and coffee flavored foods, beverages and medicaments. Also, the present invention relates to the discovery of a compound that antagonizes numerous different human T2Rs and the use thereof in assays and as a bitter taste blocker in compositions for ingestion by humans and animals.

  本发明涉及发现T2R味觉受体家族中特定人类味觉受体对咖啡等中特定苦味化合物的反应。此外，本发明涉及发现特定化合物和含有该化合物的组合物作为苦味阻断剂的功能，以及将其用作苦味阻断剂或调味剂，例如在咖啡和咖啡味食品、饮料和药品中。此外，本发明涉及发现一种对抗多种不同人类T2R的化合物，并将其用于检测中以及作为人类和动物摄入的组合物中的苦味阻断剂。
• 2-phenylpyran-4-one derivatives
  申请人：——

  公开号：US20020045644A1

  公开（公告）日：2002-04-18

  2-Phenylpyran-4-one derivatives of formula (I): 1 wherein: R 1 represents an alkyl or —NR 4 R 5 group, wherein R 4 and R 5 each independently represents a hydrogen atom or an alkyl group; R 2 represents an alkyl, C 3 -C 7 cycloalkyl, pyridyl, thienyl, naphthyl, tetrahydronaphthyl or indanyl group, or a phenyl group which may be unsubstituted or substituted by one or more halogen atoms or alkyl, trifluoromethyl, hydroxy, alkoxy, methylthic, amino, mono- or dialkylamino, hydroxalkyl or hydroxycarbonyl groups; R 3 represents a methyl, hydroxymethyl, alkoxymethyl, C 3 -C 7 cycloalkoxymethyl, benzyloxymethyl, hydroxycarbonyl, nitrile, trifluoromethyl or difluoromethyl group or a CH 2 —R 6 group wherein R 6 represents an alkyl group; and X represents a single bond, an oxygen atom, a sulfur atom or a methylene group; or pharmaceutically acceptable salts thereof, processes for their production and synthetic intermediates used in said processes, pharmaceutical compositions containing them and their use in medical treatment.

  化合物公式（I）的2-苯基吡喃-4-酮衍生物：1其中：R1代表烷基或-NR4R5基团，其中R4和R5每个独立地代表氢原子或烷基基团；R2代表烷基，C3-C7环烷基，吡啶基，噻吩基，萘基，四氢萘基或茚基，或苯基，该苯基可以是未取代的或取代了一个或多个卤素原子或烷基，三氟甲基，羟基，烷氧基，甲基硫基，氨基，单烷基或二烷基氨基，羟基烷基或羟基羧基基团；R3代表甲基，羟甲基，烷氧甲基，C3-C7环烷氧甲基，苄氧甲基，羟基羧基，腈基，三氟甲基或二氟甲基基团或CH2-R6基团，其中R6代表烷基基团；X代表单键，氧原子，硫原子或亚甲基基团；或其药学上可接受的盐，用于生产的过程以及用于该过程中使用的合成中间体，包含它们的制药组合物以及它们在医学治疗中的使用。
• New Panx-1 Blockers: Synthesis, Biological Evaluation and Molecular Dynamic Studies
  作者：Letizia Crocetti、Gabriella Guerrini、Maria Paola Giovannoni、Fabrizio Melani、Silvia Lamanna、Lorenzo Di Cesare Mannelli、Elena Lucarini、Carla Ghelardini、Junjie Wang、Gerhard Dahl

  DOI：10.3390/ijms23094827

  日期：——

  that gave the best results as in our indole series (sulphonamide functions and one/two carboxylic groups) and in Panx-1 blockers reported in the literature (sulphonic acid). Compounds 4 and 13, the latter being an analogue of the drug Probenecid, are the most potent Panx-1 blockers obtained in this study, with I = 97% and I = 93.7% at 50 µM, respectively. Both compounds, tested in a mouse model of oxaliplatin-induced

  通道蛋白 Panx-1 与一些病理学有关，例如癫痫、缺血性中风、癌症和帕金森病以及神经性疼痛。这些观察结果使 Panx-1 成为一个有趣的生物靶标。我们之前发表了一些有效的吲哚衍生物作为 Panx-1 阻滞剂，作为该领域研究的延续，我们在此报告了对其他化学支架、萘和吡唑的研究，这些支架被适当地替换为那些在我们的吲哚中给出最佳结果的功能系列（磺酰胺官能团和一个/两个羧基）和文献中报道的 Panx-1 阻断剂（磺酸）。化合物 4 和 13（后者是丙磺舒药物的类似物）是本研究中获得的最有效的 Panx-1 阻滞剂，在 50 µM 浓度下，I 分别为 97% 和 93.7%。这两种化合物在奥沙利铂诱导的神经性疼痛小鼠模型中进行了测试，显示出相似的抗过敏特性，并且能够在注射 1 nmol 和 3 nmol 剂量后 45 分钟显着提高小鼠疼痛阈值。最后，分子动力学研究和主成分分析使得识别能够将活性化合
• Compounds that inhibit (block) bitter taste in composition and use thereof
  申请人：Senomyx, Inc.

  公开号：US08076491B2

  公开（公告）日：2011-12-13

  The present invention relates to the discovery that specific human taste receptors in the T2R taste receptor family respond to particular bitter compounds present in, e.g., coffee. Also, the invention relates to the discovery of specific compounds and compositions containing that function as bitter taste blockers and the use thereof as bitter taste blockers or flavor modulators in, e.g., coffee and coffee flavored foods, beverages and medicaments. Also, the present invention relates to the discovery of a compound that antagonizes numerous different human T2Rs and the use thereof in assays and as a bitter taste blocker in compositions for ingestion by humans and animals.

  本发明涉及到发现特定的人类味觉受体T2R味觉受体家族对于存在于咖啡等物质中的特定苦味化合物作出反应。此外，本发明还涉及到发现特定的化合物和含有这些化合物的组合物，其作为苦味阻滞剂并用于咖啡和咖啡味食品、饮料和药品中作为苦味阻滞剂或味道调节剂的用途。另外，本发明还涉及到发现一种拮抗多种不同人类T2R的化合物，并将其用于测定和作为人类和动物摄入的组合物中的苦味阻滞剂。
• Compounds that inhibit (block) bitter taste in composition and methods of making same
  申请人：LI Xiaodong

  公开号：US20110207937A1

  公开（公告）日：2011-08-25

  The present invention relates to the discovery that specific human taste receptors in the T2R taste receptor family respond to particular bitter compounds present in, e.g., coffee. Also, the invention relates to the discovery of specific compounds and compositions containing that function as bitter taste blockers and the use thereof as bitter taste blockers or flavor modulators in, e.g., coffee and coffee flavored foods, beverages and medicaments. Also, the present invention relates to the discovery of a compound that antagonizes numerous different human T2Rs and the use thereof in assays and as a bitter taste blocker in compositions for ingestion by humans and animals.

  本发明涉及发现T2R味觉受体家族中的特定人类味觉受体对存在于咖啡等物质中的特定苦味化合物做出反应。此外，本发明还涉及发现特定化合物和含有该化合物的组合物，其作为苦味味觉阻滞剂的功能以及在咖啡和咖啡味食品、饮料和药品中作为苦味味觉阻滞剂或风味调节剂的使用。此外，本发明还涉及发现一种拮抗多种不同人类T2R的化合物，以及在人类和动物摄入的组合物中作为苦味味觉阻滞剂的使用和试验。