3-chloro-4-methoxy-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide | 189297-37-8

• 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: 3-chloro-4-methoxy-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide
• 英文别名: 3-chloro-4-methoxy-N'-(4-methylsulfonylphenyl)benzenecarboximidamide
• CAS: 189297-37-8
• 化学式: C₁₅H₁₅ClN₂O₃S
• 分子量: 338.815
• InChiKey: FGMVMFICYVSNMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-chloro-4-methoxy-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide 在 三乙基硼 、 正丁基氯化镁 、 碳酸氢钠 、 对甲苯磺酸 、 hydroxylamine-O-sulfonic acid 作用下， 以 异丙醇 、 甲苯 为溶剂， 反应 92.0h， 生成 4-[2-(3-chloro-4-methoxyphenyl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide
  参考文献：
  名称：

  1,2-Diarylimidazoles as Potent, Cyclooxygenase-2 Selective, and Orally Active Antiinflammatory Agents

  摘要：

  Series of 1,2-diarylimidazoles has been synthesized and found to contain highly potent and selective inhibitors of the human COX-2 enzyme. The paper describes a short synthesis of the target 1,2-diarylimidazoles starting with aryl nitriles. Different portions of the diarylimidazole (I) were modified to establish SAR. Systematic variations of the substituents in the aryl ring B have yielded very potent (IC50 = 10-100 nm) and selective (1000-12500) inhibitors of the COX-2 enzyme. The study on the influence of substituents in the imidazole ring established that a CF3 group at position 4 gives the optimum oral activity. A number of the diarylimidazoles showed excellent inhibition in the adjuvant induced arthritis model (e.g., ED50 = 0.02 mph for 22 and 34). The diarylimidazoles are also potent inhibitors of carrageenan-induced edema (ED50 = 9-30 mph) sind hyperalgesia (ED50 = 11-40 mpk). Several orally active diarylimidazoles show no GI toxicity in the rat and mouse up to 200 mpk.

  DOI：

  10.1021/jm9700225
• 作为产物：
  描述：

  3-氯-4-氟苯腈 在 三甲基铝 、 sodium methylate 作用下， 反应 40.5h， 生成 3-chloro-4-methoxy-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide
  参考文献：
  名称：

  1,2-Diarylimidazoles as Potent, Cyclooxygenase-2 Selective, and Orally Active Antiinflammatory Agents

  摘要：

  Series of 1,2-diarylimidazoles has been synthesized and found to contain highly potent and selective inhibitors of the human COX-2 enzyme. The paper describes a short synthesis of the target 1,2-diarylimidazoles starting with aryl nitriles. Different portions of the diarylimidazole (I) were modified to establish SAR. Systematic variations of the substituents in the aryl ring B have yielded very potent (IC50 = 10-100 nm) and selective (1000-12500) inhibitors of the COX-2 enzyme. The study on the influence of substituents in the imidazole ring established that a CF3 group at position 4 gives the optimum oral activity. A number of the diarylimidazoles showed excellent inhibition in the adjuvant induced arthritis model (e.g., ED50 = 0.02 mph for 22 and 34). The diarylimidazoles are also potent inhibitors of carrageenan-induced edema (ED50 = 9-30 mph) sind hyperalgesia (ED50 = 11-40 mpk). Several orally active diarylimidazoles show no GI toxicity in the rat and mouse up to 200 mpk.

  DOI：

  10.1021/jm9700225
• 作为试剂：
  描述：

  4-甲磺酰基苯胺 、 三甲基铝 、 3-氯-4-甲氧基苯甲腈 在 silica gel 、 hexane-diethyl ether 、 3-chloro-4-methoxy-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide 作用下， 以 甲苯 、 氯仿 为溶剂， 反应 22.92h， 生成 3-chloro-4-methoxy-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide
  参考文献：
  名称：

  1,2-aryl and heteroaryl substituted imidazolyl compounds for the

  摘要：

  本文介绍了一类咪唑基化合物，用于治疗炎症及与炎症相关的疾病。特别感兴趣的化合物由公式I定义：##STR1##其中R.sup.1 -R.sup.6 如说明书所述；或其药学上可接受的盐。

  公开号：

  US05616601A1

文献信息

• US5616601A
  申请人：——

  公开号：US5616601A

  公开（公告）日：1997-04-01