4-[6-(4-fluorophenyl)spiro[2.4]hept-5-en-5-yl]benzenesulfonamide | 168299-83-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-[6-(4-fluorophenyl)spiro[2.4]hept-5-en-5-yl]benzenesulfonamide
• 英文别名: 4-(6-(4-fluorophenyl)spiro[2.4]hept-5-en-5-yl)benzenesulfonamide；4-[5-(4-fluorophenyl)spiro[2.4]hept-5-en-6-yl]benzenesulfonamide
• CAS: 168299-83-0
• 化学式: C₁₉H₁₈FNO₂S
• 分子量: 343.422
• InChiKey: RSVKRWJGUDWYLS-UHFFFAOYSA-N

物化性质

• 沸点：
  511.9±60.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[6-(4-fluorophenyl)spiro[2.4]hept-5-en-5-yl]benzenesulfonamide 在 sodium acetate 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 以118 mg (39%)的产率得到4-[6-(4-fluorophenyl)spiro[2.4]hepta-4,6-dien-5-yl]benzenesulfonamide
  参考文献：
  名称：

  Pyridyl substituted spirodienes for the treatment of inflammation

  摘要：

  描述了一类取代的螺二烯类化合物，用于治疗炎症和炎症相关疾病。 特别感兴趣的化合物由公式I定义：其中A选自其中每个R1至R10都是独立选择的氢基，卤素，烷基，烷氧基，烷硫基，氰基，卤代烷基，卤代烷氧基，羟基烷基；烷氧基烷基，羟基，巯基，烷基磺酰基，卤代烷基磺酰基和磺酰氨基；其中n是选择的数字0,1,2和3；或其药学上可接受的盐。

  公开号：

  US05670510A1
• 作为产物：
  描述：

  1-<2-(4-fluorophenyl)-4,4-dicarbomethoxycyclopenten-1-yl>-4-(methylsulfonyl)benzene 在 吡啶 、 三丁基硼 、 sodium acetate 、 丙基氯化镁 、 二异丁基氢化铝 、 sodium iodide 、 hydroxylamine-O-sulfonic acid 、 锌 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 4-[6-(4-fluorophenyl)spiro[2.4]hept-5-en-5-yl]benzenesulfonamide
  参考文献：
  名称：

  Diarylspiro[2.4]heptenes as Orally Active, Highly Selective Cyclooxygenase-2 Inhibitors:  Synthesis and Structure−Activity Relationships

  摘要：

  A novel series of 5,6-diarylspiro[2.4]hept-5-enes was shown to provide highly potent and selective cyclooxygenase-2 (COX-2) inhibitors. A study of structure-activity relationships in this series suggests that 3,4-disubstituted phenyl analogs are generally more selective than 4-substituted phenyl analogs and that replacement of the methyl sulfone group on the B-phenyl ring with a sulfonamide moiety results in compounds with superior in vivo pharmacological properties, although with lower COX-2 selectivity, Several compounds have been shown to possess promising pharmacological properties in adjuvant-induced arthritis and edema analgesia models. The absence of gastrointestinal (GI) toxicity at 200 mpk of several selected compounds in rats and mice corresponds well with the weak potency for inhibition of COX-1 observed in the enzyme assay. Methyl sulfone 55 and sulfonamide 24 were shown to have superior in vivo pharmacological profiles, low GI toxicity, and good oral bioavailability and duration of action.

  DOI：

  10.1021/jm950664x

文献信息

• Compositions of a cyclooxygenase-2 selective inhibitor and a sodium ion channel blocker for the treatment of pain, inflammation or inflammation mediated disorders
  申请人：Pharmacia Corporation

  公开号：US20040220187A1

  公开（公告）日：2004-11-04

  The present invention provides compositions and methods for the treatment of pain, inflammation or inflammation-mediated disorders in a subject. More particularly, the invention provides a combination therapy for the treatment of pain, inflammation or inflammation mediated disorders comprising the administration to a subject of a sodium ion channel blocker in combination with a cyclooxygenase-2 selective inhibitor.

  本发明提供了用于治疗疼痛、炎症或炎症介导性疾病的组合物和方法。更具体地，本发明提供了一种联合疗法，用于治疗疼痛、炎症或炎症介导性疾病，包括向受试者施用钠离子通道阻滞剂与环氧合酶-2选择性抑制剂的组合。
• Method of preparing sulfmonamides from sulfones
  申请人：G. D. Searle & Co.

  公开号：US05684195A1

  公开（公告）日：1997-11-04

  A one-pot synthesis of sulfonamides from sulfones has been developed. Conversion of sulfones to the corresponding sulfinic acid salts is followed by oxidative-amination to give the sulfonamides.

  已开发出一种从磺酮合成磺胺类化合物的一锅法。将磺酮转化为相应的亚砜酸盐，然后进行氧化胺化反应以得到磺胺类化合物。
• Combination of a Cox-2 inhibitor and a DNA topoisomerase I inhibitor for treatment of neoplasia
  申请人：Masferrer L. Jaime

  公开号：US20050187172A1

  公开（公告）日：2005-08-25

  The present invention provides combinations of a Cox-2 inhibitor and a DNA topoisomerase inhibitor and methods of use thereof for preventing and/or treating neoplasia or or a neoplasia-related disorder in a subject.

  本发明提供了一种COX-2抑制剂和DNA拓扑异构酶抑制剂的组合物，以及它们的使用方法，用于预防和/或治疗受试者中的肿瘤或与肿瘤相关的疾病。
• Method for the treatment or prevention of dermatological disorders with a cyclooxygenase-2 inhibitor alone and in combination with a dermatological treatment agent and compositions therewith
  申请人：Pulaski P. Steven

  公开号：US20050014729A1

  公开（公告）日：2005-01-20

  A method for preventing or treating dermatological disorders and dermatological disorder-related complications in a subject involves a monotherapy with a Cox-2 inhibitor or a combination therapy with a Cox-2 inhibitor and a dermatological treatment agent. Also described are therapeutic compositions comprising a Cox-2 inhibitor and a dermatological treatment agent. Pharmaceutical compositions and kits for implementing the present method are also described.

  一种预防或治疗受试者的皮肤病和与皮肤病相关并发症的方法涉及使用Cox-2抑制剂进行单独治疗或与Cox-2抑制剂和皮肤治疗剂的联合治疗。还描述了包含Cox-2抑制剂和皮肤治疗剂的治疗组合物。还描述了用于实施本方法的药物组合物和工具包。
• [EN] METHOD FOR PREVENTING OR TREATING AN OPTIC NEUROPATHY<br/>[FR] METHODE PERMETTANT DE PREVENIR OU DE TRAITER UNE NEUROPATHIE OPTIQUE
  申请人：PHARMACIA CORP

  公开号：WO2005021004A1

  公开（公告）日：2005-03-10

  The present invention provides methods and compositions for the prevention and/or treatment of an optic neuropathy, comprising a Cox-2 inhibitor and an intraocular pressure reducing agent.

  本发明提供了一种预防和/或治疗视神经病变的方法和组合物，包括Cox-2抑制剂和降低眼压的药剂。