4-(5-氧代-4-苯基-2H-呋喃-3-基)苯磺酰胺 | 639785-67-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 4-(5-氧代-4-苯基-2H-呋喃-3-基)苯磺酰胺
• 英文名称: 3-phenyl-4-(4-sulfonamidophenyl)-2(5H)-furanone
• 英文别名: 3-phenyl-4-(4-sulfonamidophenyl)-2(5H)furanone；Benzenesulfonamide, 4-(2,5-dihydro-5-oxo-4-phenyl-3-furanyl)-；4-(5-oxo-4-phenyl-2H-furan-3-yl)benzenesulfonamide
• CAS: 639785-67-4
• 化学式: C₁₆H₁₃NO₄S
• 分子量: 315.35
• InChiKey: KKUOWOQXXDOGDC-UHFFFAOYSA-N

物化性质

• 熔点：
  248-250 °C
• 沸点：
  588.4±60.0 °C(Predicted)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  94.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(5-Oxo-4-phenyl-2,5-dihydro-furan-3-yl)-benzenesulfonyl chloride 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以0.42 g的产率得到4-(5-氧代-4-苯基-2H-呋喃-3-基)苯磺酰胺
  参考文献：
  名称：

  设计和合成新型rofecoxib类似物作为潜在的环氧合酶（COX-2）抑制剂：用磺酰叠氮生物甾体替代甲基磺酰药效团

  摘要：

  A组罗非昔布类似物，具有sulfonylazide（SO 2 Ñ 3）取代基取代的磺酰（SO 2 CH 3）药效团在间位-位即3-（4-甲基，4-甲氧基或4-乙氧基苯基） -4-（3-磺酰基叠氮苯基）-2（5 H）呋喃酮（7a-c）和对位3-苯基-4-（4-磺酰基叠氮苯基）-2（5 H）呋喃酮（7d），3-（C–4苯环的4-氟或4-氯苯基）-4-（4-磺酰基叠氮苯基）-2（5 H）呋喃酮（7e-f）和4-（1-氧化-4-吡啶基）- 3-苯基-2（5 H设计并合成了呋喃酮（12）作为选择性环氧合酶2（COX-2）抑制剂进行评估。体外COX-1 / COX-2酶抑制研究表明3-苯基-4-（4-磺酰基叠氮苯基）-2（5 H）呋喃酮（7d）选择性抑制COX-1（COX-1 IC 50 = 0.6659μM; COX-2 IC 50 > 100μM）和3-（4-氟苯基）-4-（4-磺酰基叠氮苯基）-2（5

  DOI：

  10.1002/jhet.5570400518

文献信息

• Design and synthesis of novel rofecoxib analogs as potential cyclooxygenase (COX-2) inhibitors: Replacement of the methylsulfonyl pharmacophore by a sulfonylazide bioisostere
  作者：Md. Jashim Uddin、P. N. Praveen Rao、Edward E. Knaus

  DOI：10.1002/jhet.5570400518

  日期：2003.9

  phenyl ring, and 4-(1-oxido-4-pyridyl)-3-phenyl-2(5H)furanone (12) were designed and synthesized for evaluation as selective cyclooxygenase-2 (COX-2) inhibitors. In vitro COX-1/COX-2 enzyme inhibition studies showed that 3-phenyl-4-(4-sulfonylazidophenyl)-2(5H)furanone (7d) inhibited COX-1 selectively (COX-1 IC50 = 0.6659 μM; COX-2 IC50 > 100 μM) and 3-(4-fluorophenyl)-4-(4-sulfonylazidophenyl)-2(5H)furanone

  A组罗非昔布类似物，具有sulfonylazide（SO 2 Ñ 3）取代基取代的磺酰（SO 2 CH 3）药效团在间位-位即3-（4-甲基，4-甲氧基或4-乙氧基苯基） -4-（3-磺酰基叠氮苯基）-2（5 H）呋喃酮（7a-c）和对位3-苯基-4-（4-磺酰基叠氮苯基）-2（5 H）呋喃酮（7d），3-（C–4苯环的4-氟或4-氯苯基）-4-（4-磺酰基叠氮苯基）-2（5 H）呋喃酮（7e-f）和4-（1-氧化-4-吡啶基）- 3-苯基-2（5 H设计并合成了呋喃酮（12）作为选择性环氧合酶2（COX-2）抑制剂进行评估。体外COX-1 / COX-2酶抑制研究表明3-苯基-4-（4-磺酰基叠氮苯基）-2（5 H）呋喃酮（7d）选择性抑制COX-1（COX-1 IC 50 = 0.6659μM; COX-2 IC 50 > 100μM）和3-（4-氟苯基）-4-（4-磺酰基叠氮苯基）-2（5
• Compositions of a cyclooxygenase-2 selective inhibitor administered under hypothermic conditions for the treatment of ischemic mediated central nervous system disorders or injury
  申请人：Stephenson T. Diane

  公开号：US20070149591A1

  公开（公告）日：2007-06-28

  Methods and compositions for the treatment of reduced blood flow to the central nervous system are provided. The method comprises administering to a subject a composition having a cyclooxygenase-2 selective inhibitor in combination with applying hypothermic conditions to the subject to provide improved neurological function in subjects with ischemic mediated central nervous system damage including stroke, traumatic brain and spinal cord injury.
• Use of COX-2 Inhibitors for the Treatment of Schizophrenia, Delusional Disorders, Affective Disorders, Autism or Tic Disorders
  申请人：Müller Norbert

  公开号：US20110130390A1

  公开（公告）日：2011-06-02

  The invention concerns the use of a COX-2 inhibitor for the treatment of psychiatric disorders such as schizophrenia, delusional disorders, affective disorders, autism or tic disorders, in particular chronic schizophrenic psychoses and schizoaffective psychoses, temporary acute psychotic disorders, depressive episodes, recurring depressive episodes, manic episodes and bipolar affective disorders. Moreover, the invention is concerned with the use of a COX-2 inhibitor, in particular celecoxib, in combination with a neuroleptic drug, in particular risperidone, or an antidepressant, for the treatment of psychiatric disorders such as schizophrenia, delusional disorders, affective disorders, autism or tic disorders.
• DASH INHIBITORS, AND USES RELATED THERETO
  申请人：Trustees of Tufts College

  公开号：US20190209525A1

  公开（公告）日：2019-07-11

  Disclosed are potent immuno-DASH inhibitors, and their use in the treatment of cell proliferative diseases.
• COMBINATION THERAPIES USING CASPASE-1 DEPENDENT ANTICANCER AGENTS AND PGE2 ANTAGONISTS
  申请人：Trustees of Tufts College

  公开号：US20200054655A1

  公开（公告）日：2020-02-20

  Disclosed are combination therapies including administration of Caspase-1 dependent anticancer agents and PGE2 antagonists, and the use of such therapies in the treatment of cell proliferative diseases.