4-methyl-5-[4-(trifluoromethyl)phenyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-methyl-5-[4-(trifluoromethyl)phenyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione
• 英文别名: 4-methyl-3-[4-(trifluoromethyl)phenyl]-1H-1,2,4-triazole-5-thione
• 化学式: C₁₀H₈F₃N₃S
• 分子量: 259.255
• InChiKey: DKVSTVJWBIXAQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3-Chloropropyl)-7-(5-methyl-isoxazol-3-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine 、 4-methyl-5-[4-(trifluoromethyl)phenyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione 在 sodium iodide potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 5-Methyl-3-[3-[3-[[4-methyl-5-[4-(trifluoromethyl)phenyl]-1,2,4-triazol-3-yl]sulfanyl]propyl]-1,2,4,5-tetrahydro-3-benzazepin-7-yl]-1,2-oxazole
  参考文献：
  名称：

  1,2,4-Triazol-3-yl-thiopropyl-tetrahydrobenzazepines:  A Series of Potent and Selective Dopamine D₃ Receptor Antagonists

  摘要：

  The discovery of new highly potent and selective dopamine D-3 receptor antagonists has recently permitted characterization of the role of the dopamine D-3 receptor in a wide range, of preclinical animal models. A novel series of 1,2,4-triazol-3-yl-thiopropyl-tetrahydrobenzazepines demonstrating a high level of D3 affinity and selectivity with an excellent pharmacokinetic profile is reported here. In particular, the pyrazolyl derivative 35 showed good oral bioavailability and brain penetration associated with high potency and selectivity in vitro. In vivo characterization of 35 confirmed that this compound blocks the expression of nicotine- and cocaine-conditioned place preference in the rat, prevents nicotine-triggered reinstatement of nicotine- seeking behavior in the rat, reduces oral operant alcohol self- administration in the mouse, increases extracellular levels of acetylcholine in the rat medial prefrontal cortex, and potentiates the amplitude of the relative cerebral blood volume response to d-amphetamine in a regionally specific manner in the rat brain.

  DOI：

  10.1021/jm0705612

文献信息

• COMPOUNDS HAVING AFFINITY FOR DOPAMINE D3 RECEPTOR AND USES THEREOF"
  申请人：Bonanomi Giorgio

  公开号：US20100016287A1

  公开（公告）日：2010-01-21

  Compounds of formula (I) wherein A is a 5 or 6 membered heteroaromatic ring or a 5 or 6 membered heterocyclic ring, and which are useful for treating mental disorders such as schizophrenia are set out herein.

  本文介绍了式子（I）中A为5或6成员杂芳环或5或6成员杂环的化合物，可用于治疗精神障碍，如精神分裂症。
• Compounds having affinity for dopamine D3 receptor and uses thereof
  申请人：Glaxo Group Limited

  公开号：US07989444B2

  公开（公告）日：2011-08-02

  Compounds of formula (I) wherein A is a 5 or 6 membered heteroaromatic ring or a 5 or 6 membered heterocyclic ring, and which are useful for treating mental disorders such as schizophrenia are set out herein.

  本文介绍了化学式(I)中A为5或6元杂芳环或5或6元杂环的化合物，这些化合物可用于治疗精神障碍，如精神分裂症。
• [EN] COMPOUNDS HAVING AFFINITY FOR DOPAMINE D3 RECEPTOR AND USES THEREOF<br/>[FR] COMPOSES PRESENTANT UNE AFFINITE POUR LE RECEPTEUR DE LA DOPAMINE D3 ET LEURS UTILISATIONS
  申请人：GLAXO GROUP LTD

  公开号：WO2005118549A3

  公开（公告）日：2006-04-13
• COMPOUNDS HAVING AFFINITY FOR DOPAMINE D3 RECEPTOR AND USES THEREOF
  申请人：GLAXO GROUP LIMITED

  公开号：EP1751163A2

  公开（公告）日：2007-02-14
• BENZAZEPINE COMPOUNDS HAVING AFFINITY FOR DOPAMINE D3 RECEPTOR AND USES THEREOF
  申请人：GLAXO GROUP LIMITED

  公开号：EP1751163B1

  公开（公告）日：2011-08-10