Cox-2-IN-1 | 787623-47-6

• 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: Cox-2-IN-1
• 英文别名: 4-[3-(7-chloro-1H-indol-3-yl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide
• CAS: 787623-47-6；787623-48-7；787623-50-1
• 化学式: C₁₈H₁₄ClF₃N₄O₂S
• 分子量: 442.849
• InChiKey: NDGPUMDPTVGJCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  99.9
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Cox-2-IN-1 生成 4-[5-(7-chloro-1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide 、 4-[5-(7-chloro-1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of 1-(4-sulfamylphenyl)-3-trifluoromethyl-5-indolyl pyrazolines as cyclooxygenase-2 (COX-2) and lipoxygenase (LOX) inhibitors

  摘要：

  A series of 20 novel 1-(4-sulfamylphenyl)-3-trifluoromethyl-5-indolyl pyrazolines were designed, synthesized, and screened in vitro for anti-inflammatory activity. These compounds were designed for evaluation as dual inhibitors of cyclooxygenases (COX-1 and COX-2) and lipoxygenases (LOX-5, LOX-12, and LOX-15) that are responsible for inflammation and pain. All pyrazoline molecules prepared are optically active and compounds that are more potent in COX-2 inhibitory activity (5a and 5f) were resolved by chiral column and each enantiomer was tested for cyclooxygenase inhibitory activity. Molecular modeling and comparison of molecular models of 5a enantiomers with that of celecoxib model shows that 5a (enantiomer-1) and 5a (enantiomer-2) have more hydrogen bonding interactions in the catalytic domain of COX-2 enzyme than celecoxib. Compounds 5a, 5e, and 5f showed moderate to good LOX-5 and LOX-15 inhibitory activity and this is comparable to that of celecoxib and more potent than rofecoxib. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.01.047
• 作为产物：
  描述：

  1,1,1-trifluoro-4-(7-chloro-1H-indol-3-yl)-but-3-en-2-one 、 4-磺酰胺基苯肼盐酸盐 以 乙醇 为溶剂， 以55%的产率得到Cox-2-IN-1
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of 1-(4-sulfamylphenyl)-3-trifluoromethyl-5-indolyl pyrazolines as cyclooxygenase-2 (COX-2) and lipoxygenase (LOX) inhibitors

  摘要：

  A series of 20 novel 1-(4-sulfamylphenyl)-3-trifluoromethyl-5-indolyl pyrazolines were designed, synthesized, and screened in vitro for anti-inflammatory activity. These compounds were designed for evaluation as dual inhibitors of cyclooxygenases (COX-1 and COX-2) and lipoxygenases (LOX-5, LOX-12, and LOX-15) that are responsible for inflammation and pain. All pyrazoline molecules prepared are optically active and compounds that are more potent in COX-2 inhibitory activity (5a and 5f) were resolved by chiral column and each enantiomer was tested for cyclooxygenase inhibitory activity. Molecular modeling and comparison of molecular models of 5a enantiomers with that of celecoxib model shows that 5a (enantiomer-1) and 5a (enantiomer-2) have more hydrogen bonding interactions in the catalytic domain of COX-2 enzyme than celecoxib. Compounds 5a, 5e, and 5f showed moderate to good LOX-5 and LOX-15 inhibitory activity and this is comparable to that of celecoxib and more potent than rofecoxib. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.01.047

文献信息

• [EN] (-)1-(4-SULFAMYLARYL)-3-SUBSTITUTED-5-HETEROARYL-2 PYRAZOLINES AS INHIBITORS OF CYCLOOXYGENASE-2<br/>[FR] (-)1-(4-SULFAMYRYL)-3-SUBSTITUE-5-HETEROARYL-2 PYRAZOLINES UTILISEES COMME INHIBITEURS DE LA CYCLOOXYGENASE-2
  申请人：UNIV TEMPLE

  公开号：WO2004093829A2

  公开（公告）日：2004-11-04

  The (-)-enantiomers of the optically active compounds of the formula (I) wherein X, Z and R5 are as defined herein, and pharmaceutically acceptable salts thereof, are inhibitors of cyclooxygenase-2 activity. The compounds are useful for treating cyclooxygenase-mediated disorders, including, for example, inflammation, neoplastic disorders and angiogenesis-mediated disorders.
• Design, synthesis, and biological evaluation of 1-(4-sulfamylphenyl)-3-trifluoromethyl-5-indolyl pyrazolines as cyclooxygenase-2 (COX-2) and lipoxygenase (LOX) inhibitors
  作者：M.V. Ramana Reddy、Vinay K. Billa、Venkat R. Pallela、Muralidhar R. Mallireddigari、Rengasamy Boominathan、Jerome L. Gabriel、E. Premkumar Reddy

  DOI：10.1016/j.bmc.2008.01.047

  日期：2008.4.1

  A series of 20 novel 1-(4-sulfamylphenyl)-3-trifluoromethyl-5-indolyl pyrazolines were designed, synthesized, and screened in vitro for anti-inflammatory activity. These compounds were designed for evaluation as dual inhibitors of cyclooxygenases (COX-1 and COX-2) and lipoxygenases (LOX-5, LOX-12, and LOX-15) that are responsible for inflammation and pain. All pyrazoline molecules prepared are optically active and compounds that are more potent in COX-2 inhibitory activity (5a and 5f) were resolved by chiral column and each enantiomer was tested for cyclooxygenase inhibitory activity. Molecular modeling and comparison of molecular models of 5a enantiomers with that of celecoxib model shows that 5a (enantiomer-1) and 5a (enantiomer-2) have more hydrogen bonding interactions in the catalytic domain of COX-2 enzyme than celecoxib. Compounds 5a, 5e, and 5f showed moderate to good LOX-5 and LOX-15 inhibitory activity and this is comparable to that of celecoxib and more potent than rofecoxib. (c) 2008 Elsevier Ltd. All rights reserved.