4-(Dibenzylsulfamoyl)benzoyl chloride | 263242-02-0

• 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-(Dibenzylsulfamoyl)benzoyl chloride
• CAS: 263242-02-0
• 化学式: C₂₁H₁₈ClNO₃S
• 分子量: 399.898
• InChiKey: GNDKFEOAJGULAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(Dibenzylsulfamoyl)benzoyl chloride 在 magnesium 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.5h， 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 、 氯化亚砜 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 8.5h， 生成 4-(Dibenzylsulfamoyl)benzoyl chloride
  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

• 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。
• 2-PHENYLPYRAN-4-ONE DERIVATIVES
  申请人：Almirall Prodesfarma, S.A.

  公开号：EP1115716A1

  公开（公告）日：2001-07-18
• US6518303B2
  申请人：——

  公开号：US6518303B2

  公开（公告）日：2003-02-11
• [EN] 2-PHENYLPYRAN-4-ONE DERIVATIVES<br/>[FR] DERIVES DE 2-PHENYLPYRAN-4-ONE
  申请人：ALMIRALL PRODESFARMA SA

  公开号：WO2000018753A1

  公开（公告）日：2000-04-06

  2-Phenylpyran-4-one derivatives of formula (I), wherein R1 represents an alkyl or -NR4R5 group, wherein R?4 and R5¿ each independently represents a hydrogen atom or an alkyl group; R2 represents an alkyl, C¿3?-C7 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, methylthio, amino, mono- or dialkylamino, hydroxyalkyl or hydroxycarbonyl groups; R?3¿ represents a methyl, hydroxymethyl, alkoxymethyl, C¿3?-C7 cycloalkoxymethyl, benzyloxymethyl, hydroxycarbonyl, nitrile, trifluoromethyl or difluoromethyl group or a CH2-R?6¿ group wherein R6 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.
• Synthesis and Biological Evaluation of 2-Phenylpyran-4-ones:  A New Class of Orally Active Cyclooxygenase-2 Inhibitors
  作者：Francisco Caturla、Juan-Miguel Jiménez、Núria Godessart、Mercè Amat、Alvaro Cárdenas、Lídia Soca、Jordi Beleta、Hamish Ryder、María I. Crespo

  DOI：10.1021/jm049882t

  日期：2004.7.1

  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.