5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(4-methylpiperazin-1-yl)-1H-pyrazole-3-carboxamide | 953758-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(4-methylpiperazin-1-yl)-1H-pyrazole-3-carboxamide
• 英文别名: 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(4-methylpiperazin-1-yl)-1Hpyrazole-3-carboxamide；5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(4-methylpiperazin-1-yl)pyrazole-3-carboxamide
• CAS: 953758-69-5
• 化学式: C₂₂H₂₂Cl₃N₅O
• 分子量: 478.809
• InChiKey: JZPDSTUBURERTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4-二氯苯肼盐酸盐 在 氯化亚砜 、 水 、 溶剂黄146 、 三乙胺 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 50.0h， 生成 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(4-methylpiperazin-1-yl)-1H-pyrazole-3-carboxamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of CB1 cannabinoid receptor ligands derived from the 1,5-diarylpyrazole scaffold

  摘要：

  The CB1 receptor belongs to the G-protein-coupled receptor superfamily. CB1 antagonism has been considered as a new therapeutic target for the treatment of obesity. In this study, we report the synthesis and in vitro binding affinity assay of some 1,5-diarylpyrazole scaffold compounds. The binding results showed that some of the target compounds had an excellent potency toward the CB1 receptor with IC(50) values lying at the nanomole level.

  DOI：

  10.3109/14756366.2010.491794

文献信息

• Repurposing of a drug scaffold: Identification of novel sila analogues of rimonabant as potent antitubercular agents
  作者：Remya Ramesh、Rahul D. Shingare、Vinod Kumar、Amitesh Anand、Swetha B、Sridhar Veeraraghavan、Srikant Viswanadha、Ramesh Ummanni、Rajesh Gokhale、D. Srinivasa Reddy

  DOI：10.1016/j.ejmech.2016.07.009

  日期：2016.10

  The structural similarity between an MmpL3 inhibitor BM212, and a cannabinoid receptor modulator rimonabant, prompted us to investigate the anti-tubercular activity of rimonabant and its analogues. Further optimization, particularly through incorporation of silicon into the scaffold, resulted in new compounds with significant improvement in anti-tubercular activity against Mycobacterium tuberculosis (H37Rv). The sila analogue 18a was found to be the most potent antimycobacterial compound (MIC, 31 ng/mL) from this series with an excellent selectivity index. (C) 2016 Elsevier Masson SAS. All rights reserved.