N-(4-Methylsulfanyl-phenyl)-pyridine-2-carboxamidine | 812692-63-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-(4-Methylsulfanyl-phenyl)-pyridine-2-carboxamidine
• 英文别名: N'-(4-methylsulfanylphenyl)pyridine-2-carboximidamide
• CAS: 812692-63-0
• 化学式: C₁₃H₁₃N₃S
• 分子量: 243.332
• InChiKey: PPEXBZUTFBAWBU-UHFFFAOYSA-N

物化性质

• 沸点：
  386.6±48.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  76.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-Methylsulfanyl-phenyl)-pyridine-2-carboxamidine 在 碳酸氢钠 、 对甲苯磺酸 作用下， 以 异丙醇 、 甲苯 为溶剂， 反应 8.5h， 生成
  参考文献：
  名称：

  Selective Cyclooxygenase-2 Inhibitors:  Heteroaryl Modified 1,2-Diarylimidazoles Are Potent, Orally Active Antiinflammatory Agents

  摘要：

  A series of heteroaryl modified 1,2-diarylimidazoles has been synthesized and found to be potent and highly selective (1000-9000-fold) inhibitors of the human COX-2. 3-Pyridyl derived COX-2 selective inhibitor (25) exhibited excellent activity in acute (carrageenan induced paw edema, ED50 = 5.4 mg/kg) and chronic (adjuvant induced arthritis, ED50 = 0.25 mg/kg) models of inflammation. The relatively long half-life of 25 in rat and dog prompted investigation of the pyridyl and other heteroaromatic systems containing potential metabolic functionalities. A number of substituted pyridyl and thiazole containing compounds (e.g., 44, 46, 54, 76, and 78) demonstrated excellent oral activity in every efficacy model evaluated. Several orally active diarylimidazoles exhibited desirable pharmacokinetics profiles and showed no CI toxicity in the rat up to 100 mg/kg in both acute and chronic models. The paper describes facile and practical syntheses of the targeted diarylimidazoles. The structure-activity relationships and antiinflammatory properties of a series of diarylimidazoles are discussed.

  DOI：

  10.1021/jm0000719
• 作为产物：
  描述：

  2-氰基吡啶 、 4-氨基茴香硫醚 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 N-(4-Methylsulfanyl-phenyl)-pyridine-2-carboxamidine
  参考文献：
  名称：

  Selective Cyclooxygenase-2 Inhibitors:  Heteroaryl Modified 1,2-Diarylimidazoles Are Potent, Orally Active Antiinflammatory Agents

  摘要：

  A series of heteroaryl modified 1,2-diarylimidazoles has been synthesized and found to be potent and highly selective (1000-9000-fold) inhibitors of the human COX-2. 3-Pyridyl derived COX-2 selective inhibitor (25) exhibited excellent activity in acute (carrageenan induced paw edema, ED50 = 5.4 mg/kg) and chronic (adjuvant induced arthritis, ED50 = 0.25 mg/kg) models of inflammation. The relatively long half-life of 25 in rat and dog prompted investigation of the pyridyl and other heteroaromatic systems containing potential metabolic functionalities. A number of substituted pyridyl and thiazole containing compounds (e.g., 44, 46, 54, 76, and 78) demonstrated excellent oral activity in every efficacy model evaluated. Several orally active diarylimidazoles exhibited desirable pharmacokinetics profiles and showed no CI toxicity in the rat up to 100 mg/kg in both acute and chronic models. The paper describes facile and practical syntheses of the targeted diarylimidazoles. The structure-activity relationships and antiinflammatory properties of a series of diarylimidazoles are discussed.

  DOI：

  10.1021/jm0000719

文献信息

• Novel pyrimidon derivatives
  申请人：Orchid Chemical & Pharmaceuticals Limited

  公开号：US20040259891A1

  公开（公告）日：2004-12-23

  The present invention relates to novel pyrimidones of the general formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their hydrates, their solvates, their pharmaceutically acceptable salts and pharmaceutically acceptable compositions containing them. The present invention more particularly novel pyrimidones of the general formula (I). 1

  本发明涉及一种新的嘧啶酮，其通式为(I)，它们的衍生物、类似物、互变异构体、立体异构体、多晶形态、水合物、溶剂合物、药用盐及含有它们的药用成分。本发明更具体地涉及通式(I)的新嘧啶酮。
• US7365069B2
  申请人：——

  公开号：US7365069B2

  公开（公告）日：2008-04-29
• Selective Cyclooxygenase-2 Inhibitors:  Heteroaryl Modified 1,2-Diarylimidazoles Are Potent, Orally Active Antiinflammatory Agents
  作者：Ish K. Khanna、Yi Yu、Renee M. Huff、Richard M. Weier、Xiangdong Xu、Francis J. Koszyk、Paul W. Collins、J. Nita Cogburn、Peter C. Isakson、Carol M. Koboldt、Jaime L. Masferrer、William E. Perkins、Karen Seibert、Amy W. Veenhuizen、Jinhua Yuan、Dai-Chang Yang、Yan Y. Zhang

  DOI：10.1021/jm0000719

  日期：2000.8.1

  A series of heteroaryl modified 1,2-diarylimidazoles has been synthesized and found to be potent and highly selective (1000-9000-fold) inhibitors of the human COX-2. 3-Pyridyl derived COX-2 selective inhibitor (25) exhibited excellent activity in acute (carrageenan induced paw edema, ED50 = 5.4 mg/kg) and chronic (adjuvant induced arthritis, ED50 = 0.25 mg/kg) models of inflammation. The relatively long half-life of 25 in rat and dog prompted investigation of the pyridyl and other heteroaromatic systems containing potential metabolic functionalities. A number of substituted pyridyl and thiazole containing compounds (e.g., 44, 46, 54, 76, and 78) demonstrated excellent oral activity in every efficacy model evaluated. Several orally active diarylimidazoles exhibited desirable pharmacokinetics profiles and showed no CI toxicity in the rat up to 100 mg/kg in both acute and chronic models. The paper describes facile and practical syntheses of the targeted diarylimidazoles. The structure-activity relationships and antiinflammatory properties of a series of diarylimidazoles are discussed.