1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-(2,2-difluoropropyl)-4-vinyl-1Hpyrazole-3-carboxamide | 1149341-28-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-(2,2-difluoropropyl)-4-vinyl-1Hpyrazole-3-carboxamide
• 英文别名: 1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-(2,2-difluoropropyl)-4-ethenylpyrazole-3-carboxamide
• CAS: 1149341-28-5
• 化学式: C₂₁H₁₇Cl₂F₂N₃O
• 分子量: 436.288
• InChiKey: NAQHMNPTBXHPTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-(2,2-difluoropropyl)-4-vinyl-1Hpyrazole-3-carboxamide 、 9-硼双环[3.3.1]壬烷 以 四氢呋喃 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Discovery of 2-(2-Chlorophenyl)-3-(4-chlorophenyl)-7-(2,2-difluoropropyl)-6,7-dihydro-2H-pyrazolo[3,4-f][1,4]oxazepin-8(5H)-one (PF-514273), a Novel, Bicyclic Lactam-Based Cannabinoid-1 Receptor Antagonist for the Treatment of Obesity

  摘要：

  We report the design, synthesis, and structure-activity relationships of novel bicyclic lactam-based cannabinoid type 1 (CB,) receptor antagonists. Members of these series are potent, selective antagonists in in vitro/in vivo efficacy models of CB, antagonism and exhibit robust oral activity in rodent models of food intake. These efforts led to the identification of 19d, which has been advanced to human clinical trials for weight management.

  DOI：

  10.1021/jm900255t
• 作为产物：
  描述：

  2,2-二氟丙胺盐酸盐 、 1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-vinyl-1H-pyrazole-3-carboxylic acid 在 二乙基异丙基胺 、 1-丙基磷酸酐 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 以1.4 g的产率得到1-(2-chlorophenyl)-5-(4-chlorophenyl)-N-(2,2-difluoropropyl)-4-vinyl-1Hpyrazole-3-carboxamide
  参考文献：
  名称：

  Discovery of 2-(2-Chlorophenyl)-3-(4-chlorophenyl)-7-(2,2-difluoropropyl)-6,7-dihydro-2H-pyrazolo[3,4-f][1,4]oxazepin-8(5H)-one (PF-514273), a Novel, Bicyclic Lactam-Based Cannabinoid-1 Receptor Antagonist for the Treatment of Obesity

  摘要：

  We report the design, synthesis, and structure-activity relationships of novel bicyclic lactam-based cannabinoid type 1 (CB,) receptor antagonists. Members of these series are potent, selective antagonists in in vitro/in vivo efficacy models of CB, antagonism and exhibit robust oral activity in rodent models of food intake. These efforts led to the identification of 19d, which has been advanced to human clinical trials for weight management.

  DOI：

  10.1021/jm900255t

文献信息

• Discovery of 2-(2-Chlorophenyl)-3-(4-chlorophenyl)-7-(2,2-difluoropropyl)-6,7-dihydro-2<i>H</i>-pyrazolo[3,4-<i>f</i>][1,4]oxazepin-8(5<i>H</i>)-one (PF-514273), a Novel, Bicyclic Lactam-Based Cannabinoid-1 Receptor Antagonist for the Treatment of Obesity
  作者：Robert L. Dow、Philip A. Carpino、John R. Hadcock、Shawn C. Black、Philip A. Iredale、Paul DaSilva-Jardine、Steven R. Schneider、Ernest S. Paight、David A. Griffith、Dennis O. Scott、Rebecca E. O’Connor、Chudy I. Nduaka

  DOI：10.1021/jm900255t

  日期：2009.5.14

  We report the design, synthesis, and structure-activity relationships of novel bicyclic lactam-based cannabinoid type 1 (CB,) receptor antagonists. Members of these series are potent, selective antagonists in in vitro/in vivo efficacy models of CB, antagonism and exhibit robust oral activity in rodent models of food intake. These efforts led to the identification of 19d, which has been advanced to human clinical trials for weight management.