1-(2-(4-methoxyphenyl)cyclopenten-1-yl)4-(methylsulfonyl)benzene | 159429-69-3

• 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: 1-(2-(4-methoxyphenyl)cyclopenten-1-yl)4-(methylsulfonyl)benzene
• 英文别名: 1-Methoxy-4-[2-(4-methylsulfonylphenyl)-1-cyclopentenyl]benzene；1-methoxy-4-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene
• CAS: 159429-69-3
• 化学式: C₁₉H₂₀O₃S
• 分子量: 328.432
• InChiKey: RAUHMMADXJJVRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-(4-methoxyphenyl)cyclopenten-1-yl)4-(methylsulfonyl)benzene 在 三溴化硼 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以73%的产率得到4-[2-(4-(methanesulfonyl)phenyl]cyclopent-1-enyl)phenol
  参考文献：
  名称：

  Synthesis and evaluation in vitro and in vivo of a 11C-labeled cyclooxygenase-2 (COX-2) inhibitor

  摘要：

  The radiosynthesis and radiopharmacological evaluation of 1-[C-11] methoxy-4-(2-(4-(methanesulfonyl)phenyl)cyclopent-1-enyl)-benzene [C-11]5 as novel PET radiotracer for imaging of COX-2 expression is described\. The radiotracer was prepared via O-methylation reaction with [C-11] methyl iodide in 19% decay-corrected radiochemical yield at a specific activity of 20-25 GBq/mu mol at the end-of-synthesis within 35 min. The radiotracer [C-11]5 was evaluated in vitro using various pro-inflammatory and tumor cell lines showing high functional expression of COX-2 at baseline or after induction. In vivo biodistribution of compound [C-11] 5 was characterized in male Wistar rats. Compound [C-11]5 was rapidly metabolized in rat plasma, and more pronounced, in mouse plasma. In vivo kinetics and tumor uptake were demonstrated by dynamic small animal PET studies in a mouse tumor xenograft model. Tumor uptake of radioactivity was clearly visible overtime. However, radioactivity uptake in the tumor could not be blocked by the pre-injection of nonradioactive compound 5. Therefore, it can be concluded that radioactivity uptake in the tumor was not COX-2 mediated. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.016
• 作为产物：
  描述：

  1-(2-溴环戊烯-1-基)-4-(甲硫基)苯 在 Oxone 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 甲苯 为溶剂， 反应 4.0h， 生成 1-(2-(4-methoxyphenyl)cyclopenten-1-yl)4-(methylsulfonyl)benzene
  参考文献：
  名称：

  1,2-二芳基环戊烯作为选择性环加氧酶-2抑制剂和口服活性抗炎药。

  摘要：

  一系列的1,2-二芳基环戊烯甲基砜和磺酰胺已被证明是非常有效的选择性环氧化酶-2（COX-2）抑制剂。甲基砜类似物7具有出色的COX-2活性，IC50范围为0.003（7f，n）至0.87（7o）microM。此外，大多数7的类似物对COX-1酶均无活性（IC50> 100 microM）。用磺酰胺基团取代甲基砜部分产生的效力稍强（通常为2-5倍），但选择性较低的COX-2抑制剂，这主要是由于COX-1活性增加（20-> 100倍）。然而，在许多情况下，通过简单地在苯基的3-位引入取代基，可以提高对磺酰胺8的体外COX-1 / COX-2选择性。此外，体外选择性随取代基的大小和数量而增加，如8k（8000）> 8j（1900）> 8i（500）> 8h（100）的选择性趋势所示。更重要的是，在已建立佐剂诱发的关节炎的大鼠模型中，磺酰胺COX-2抑制剂显示出大大增强的口服活性，在1 mg时的抑制值为79

  DOI：

  10.1021/jm00022a023

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。
• 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。
• Method for the treatment and prevention of pain and inflammation with glucosamine and a cyclooxygenase-2 selective inhibitor and compositions therefor
  申请人：Pharmacia Corporation

  公开号：US20030114418A1

  公开（公告）日：2003-06-19

  A method of treating, preventing, or inhibiting pain, inflammation or inflammation-associated disorder in a subject in need of such treatment or prevention provides for treating the subject with glucosamine and a cyclooxygenase-2 selective inhibitor or prodrug thereof, wherein the amount of glucosamine and the amount of a cyclooxygenase-2 selective inhibitor or prodrug thereof together constitute a pain or inflammation suppressing treatment or prevention effective amount of the composition. Compositions and pharmaceutical compositions that contain glucosamine and a cyclooxygenase-2 selective inhibitor are also disclosed.

  一种治疗、预防或抑制需要此类治疗或预防的受试者的疼痛、炎症或与炎症相关疾病的方法包括使用氨基葡萄糖和环氧合酶-2选择性抑制剂或其前药来治疗受试者，其中氨基葡萄糖的量和环氧合酶-2选择性抑制剂或其前药的量共同构成组合物的疼痛或炎症抑制治疗或预防的有效量。还公开了含有氨基葡萄糖和环氧合酶-2选择性抑制剂的组合物和药物组合物。