2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]-1,5,5-trimethyl-1,5-dihydroimidazol-4-thione | 1170700-85-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]-1,5,5-trimethyl-1,5-dihydroimidazol-4-thione
• 英文别名: 2-[5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazol-3-yl]-1,5,5-trimethyl-1,5-dihydro-imidazole-4-thione；2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]-1,5,5-trimethylimidazole-4-thione
• CAS: 1170700-85-2
• 化学式: C₂₂H₁₉Cl₃N₄S
• 分子量: 477.845
• InChiKey: CYHSJMXZGJNACF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]-1,5,5-trimethyl-1,5-dihydroimidazol-4-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以77%的产率得到2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]-1,5,5-trimethyl-1,5-dihydroimidazol-4-thione
  参考文献：
  名称：

  Imidazol-4-one and Imidazole-4-thione Compounds

  摘要：

  咪唑-4-酮或咪唑-4-硫酮化合物的化学式（I）：其中X，R1，R2，R3，R4，R5和R6在此定义。还揭示了使用这些化合物治疗大麻素受体介导的疾病的方法。

  公开号：

  US20100113546A1

文献信息

• Imidazol-4-one and imidazole-4-thione compounds
  申请人：Shia Kak-Shan

  公开号：US08354442B2

  公开（公告）日：2013-01-15

  Imidazol-4-one or imidazole-4-thione compounds of formula (I): wherein X, R1, R2, R3, R4, R5, and R6 are defined herein. Also disclosed is a method for treating a cannabinoid receptor-mediated disorder with these compounds.

  式(I)中的咪唑-4-酮或咪唑-4-硫酮化合物：其中X，R1，R2，R3，R4，R5和R6在此定义。还公开了使用这些化合物治疗大麻素受体介导的疾病的方法。
• Discovery of 2-[5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-ethyl-1<i>H</i>-pyrazol-3-yl]-1,5,5-trimethyl-1,5-dihydro-imidazol-4-thione (BPR-890) via an Active Metabolite. A Novel, Potent and Selective Cannabinoid-1 Receptor Inverse Agonist with High Antiobesity Efficacy in DIO Mice
  作者：Chien-Huang Wu、Ming-Shiu Hung、Jen-Shin Song、Teng-Kuang Yeh、Ming-Chen Chou、Cheng-Ming Chu、Jiing-Jyh Jan、Min-Tsang Hsieh、Shi-Liang Tseng、Chun-Ping Chang、Wan-Ping Hsieh、Yinchiu Lin、Yen-Nan Yeh、Wan-Ling Chung、Chun-Wei Kuo、Chin-Yu Lin、Horng-Shing Shy、Yu-Sheng Chao、Kak-Shan Shia

  DOI：10.1021/jm900471u

  日期：2009.7.23

  By using the active metabolite 5 as an initial template, further structural modifications led to the identification of the titled compound 24 (BPR-890) as a highly potent CB I inverse agonist possessing an excellent CB2/1 selectivity and remarkable in vivo efficacy in diet-induced obese mice with a minimum effective dose as low as 0.03 mg/kg (po qd) at the end of the 30-day chronic study. Current SAR studies along with those of many existing rimonabant-mimicking molecules imply that around the pyrazole C3-position, a rigid and deep binding pocket should exist for CB1 receptor. In addition, relative to the conventional carboxamide carbonyl, serving as a key hydrogen-bond acceptor during ligand-CB1 receptor interaction, the corresponding polarizable thione carbonyl might play a more critical role in stabilizing the Asp366-Lys192 salt bridge in the proposed CB1-receptor homology model and inducing significant selectivity for CB1R over CB2R.
• US8354442B2
  申请人：——

  公开号：US8354442B2

  公开（公告）日：2013-01-15
• [EN] IMIDAZOL-4-ONE AND IMIDAZOLE-4-THIONE COMPOUNDS<br/>[FR] COMPOSÉS D'IMIDAZOL-4-ONE OU D'IMIDASOLE-4-THIONE
  申请人：NAT HEALTH RESEARCH INSTITUTES

  公开号：WO2010062686A2

  公开（公告）日：2010-06-03

  Imidazol-4-one or imidazole-4-thione compounds of formula (I) shown in the specification. Also disclosed is a method for treating a cannabinoid receptor-mediated disorder with these compounds.