5-(4-氯苯基)-1-(2,4-二氯苯基)-3-己基-1,2,4-三唑 | 611207-11-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-(4-氯苯基)-1-(2,4-二氯苯基)-3-己基-1,2,4-三唑
• 英文名称: LH-21
• 英文别名: 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-3-hexyl-1h-1,2,4-triazole；5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-3-hexyl-1,2,4-triazole
• CAS: 611207-11-5
• 化学式: C₂₀H₂₀Cl₃N₃
• 分子量: 408.758
• InChiKey: USJFDADYVUDVAX-UHFFFAOYSA-N

物化性质

• 溶解度：
  乙醇中≤10mg/ml；DMSO中≤10mg/ml；二甲基甲酰胺中≤10mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  庚酸酐 在 硫酸 、 sodium acetate 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 23.0h， 生成 5-(4-氯苯基)-1-(2,4-二氯苯基)-3-己基-1,2,4-三唑
  参考文献：
  名称：

  Discovery of 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-3-hexyl-1H-1,2,4-triazole, a Novel in Vivo Cannabinoid Antagonist Containing a 1,2,4-Triazole Motif

  摘要：

  A new series of 1,2,4-triazoles have been prepared and the evaluation of their cannabinoid properties have been carried out. Compound 8 showed cannabinoid silent antagonist activity in mouse vas deferens and guinea pig ileum preparations and in vivo assays (cannabinoid tetrad) in mouse. It did not have intrinsic activity in these bioassays, and therefore, it did not behave as a partial agonist or an inverse agonist.

  DOI：

  10.1021/jm031099y

文献信息

• Synthesis of 1,3,5-trisubstituted-1,2,4-triazoles by microwave-assisted N-acylation of amide derivatives and the consecutive reaction with hydrazine hydrochlorides
  作者：Jongbok Lee、Myengchan Hong、Yoonchul Jung、Eun Jin Cho、Hakjune Rhee

  DOI：10.1016/j.tet.2012.01.003

  日期：2012.2

  Facile and efficient procedures for the N-acylation reaction of amide derivatives with various acid anhydrides and the cyclization reaction of N-acylated amide derivatives with various hydrazine hydrochlorides were described. The reactions were carried out under microwave irradiation to give products in good yields in a few minutes. The synthesis of 1,3,5-trisubstituted-1,2,4-triazoles from benzamides

  描述了酰胺衍生物与各种酸酐的N-酰化反应以及N-酰化的酰胺衍生物与各种肼盐酸盐的环化反应的简便有效的方法。反应在微波辐射下进行，在几分钟内以高收率得到产物。由苯甲酰胺合成1,3,5-三取代-1,2,4-三唑也可以通过简单的一锅顺序反应来完成。
• [EN] 1,5-DIARYL-PYRAZOLES AND THEIR USE AS CANNABINOID RECEPTOR NEUTRAL ANTAGONISTS<br/>[FR] 1,5-DIARYL-PYRAZOLES ET LEUR UTILISATION COMME ANTAGONISTES NEUTRES DES RÉCEPTEURS CANNABINOÏDES
  申请人：UNIV ABERDEEN

  公开号：WO2010020762A1

  公开（公告）日：2010-02-25

  The present invention pertains to cannabinoid (CB) receptor and cannabinoid-like receptor neutral antagonists, and especially CB1 neutral antagonists of Formula (I). The present invention also pertains to these compounds for use in the treatment of diseases and disorders that are ameliorated by treatment with a neutral antagonist of the cannabinoid type 1 (CB1) receptor or a non-CB1/non-CB2 cannabinoid-like receptor, for example: an eating disorder; obesity; cardiovascular disease; a disease or disorder characterised by an addiction component; addiction; withdrawal; smoking addiction; smoking withdrawal; drug addiction; drug withdrawal; smoking cessation therapy; a bone disease or disorder; osteoporosis, Paget' s disease of bone; bone related cancer; breast cancer; breast cancer metastases; breast cancer which has metastasised to bone; cancer associated with activation or inactivation of a non-CB1/non-CB2 cannabinoid-like receptor,

  本发明涉及大麻素（CB）受体和类大麻素受体中和拮抗剂，特别是公式（I）的CB1中和拮抗剂。本发明还涉及这些化合物在治疗通过使用大麻素类型1（CB1）受体的中和拮抗剂或非CB1/非CB2类大麻素受体得到改善的疾病和疾病的使用，例如：进食障碍；肥胖；心血管疾病；由成瘾成分特征的疾病或障碍；成瘾；戒断；吸烟成瘾；戒烟；药物成瘾；戒毒；戒烟疗法；骨骼疾病或障碍；骨质疏松症，Paget骨病；与激活或失活非CB1/非CB2类大麻素受体相关的癌症。
• 1,5-Diaryl-Pyrazoles As Cannabinoid Receptor Neutral Antagonists Useful As Therapeutic Agents
  申请人：Greig Iain Robert

  公开号：US20100022611A1

  公开（公告）日：2010-01-28

  The present invention pertains to cannabinoid (CB) receptor neutral antagonists, and especially CB1 neutral antagonists, and including, for example, certain 1,5 -di-aryl-pyrazole compounds. The present invention also pertains to the use of such compounds in the treatment of diseases and disorders that are ameliorated by treatment with a neutral antagonist of the cannabinoid type 1 (CB1) receptor, for example: an eating disorder; obesity; a disease or disorder characterised by an addiction component; addiction; withdrawal; smoking addiction; smoking withdrawal; drug addiction; drug withdrawal; smoking cessation therapy; a bone disease or disorder; osteoporosis, Paget's disease of bone; bone related cancer; a disease or disorder with an inflammatory or autoimmune component; rheumatoid arthritis; inflammatory bowel disease; psoriasis; a psychiatric disease or disorder; anxiety; mania; schizophrenia; a disease or disorder characterised by impairment of memory and/or loss of cognitive function; memory impairment; loss of cognitive function; Parkinson's disease; Alzheimer's disease; dementia; a cardiovascular disease or disorder; congestive heart failure; cardiac hypertrophy; and myocardial infarction.

  本发明涉及大麻素（CB）受体中和拮抗剂，特别是CB1中和拮抗剂，包括例如某些1,5-二芳基吡唑化合物。本发明还涉及使用这些化合物治疗通过与大麻素类型1（CB1）受体的中和拮抗剂治疗改善的疾病和疾病，例如：进食障碍；肥胖症；以成瘾成分为特征的疾病或疾病；成瘾；戒断；吸烟成瘾；戒烟；药物成瘾；药物戒断；戒烟疗法；骨疾病或疾病；骨质疏松症，骨的帕吉特病；与骨有关的癌症；具有炎症或自身免疫成分的疾病或疾病；类风湿性关节炎；炎症性肠病；牛皮癣；精神疾病或疾病；焦虑症；狂躁症；精神分裂症；以记忆受损和/或认知功能丧失为特征的疾病或疾病；记忆障碍；认知功能丧失；帕金森病；阿尔茨海默病；痴呆；心血管疾病或疾病；充血性心力衰竭；心脏肥大；心肌梗塞。
• Novel derivatives of 3-alkyl-1,5-diaryl-1H-1,2,4-triazoles and their pharmacological evaluation as CB1 cannabinoid ligands
  作者：Laura Hernandez-Folgado、Pilar Goya、Jordi Frigola、María Rosa Cuberes、Alberto Dordal、Jörg Holenz、Nadine Jagerovic

  DOI：10.1007/s00706-008-0890-8

  日期：2008.9

  In a previous study, we have identified 3-alkyl-1,5-diaryl-1H-1,2,4-triazoles to be a novel class of cannabinoid type-1 (CB1) receptor antagonists. However, the synthesis yields for the ligands were low. Here we present an alternative synthesis pathway with improved yields. In addition, we have synthezised new structural derivatives and studied their results in competitive radioligand binding assays for cannabinoid receptors.
• 1,5-DIARYL-PYRAZOLES AS CANNABINOID RECEPTOR NEUTRAL ANTAGONISTS USEFUL AS THERAPEUTIC AGENTS
  申请人：The University Court of The University of Aberdeen

  公开号：EP2125747A1

  公开（公告）日：2009-12-02