1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide | 874368-76-0

• 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)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide
• 英文别名: 1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-N-(1-piperidyl)pyrazole-3-carboxamide；1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide
• CAS: 874368-76-0
• 化学式: C₂₂H₂₂Cl₂N₄O
• 分子量: 429.349
• InChiKey: XQFWOCBFCCQKMR-UHFFFAOYSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 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：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid 在 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide
  参考文献：
  名称：

  Discovery of Rimonabant and its potential analogues as anti-TB drug candidates

  摘要：

  Rimonabant and its analogues have been synthesized in moderate to good yields using a simple synthetic route. All the newly synthesized compounds were subjected to in vitro screening against M. tuberculosis and M. smegmatis. The most potent analogue JMG-14 exhibits MIC value of 3.13 compared to 3.25 and 50 A mu g/ml for ethambutol and pyrazinamide, respectively. The molecular docking reveals that pyrazole ring, number and position of halogen atoms play a crucial role in deciding interactions with MTCYP-121. These findings open up a new avenue in the search of potent anti-TB drugs with rimonabant and its novel analogue JMG-14 as lead molecules.

  DOI：

  10.1007/s00044-015-1346-4

文献信息

• [EN] PYRAZOLE CARBOXYLIC ACID ANALOGUES AS ANTI-MYCOBACTERIAL DRUG CANDIDATES<br/>[FR] ANALOGUES D'ACIDE PYRAZOLE CARBOXYLIQUE EN TANT QUE CANDIDATS MÉDICAMENTS ANTI-MYCOBACTÉRIENS
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2014174457A1

  公开（公告）日：2014-10-30

  The present invention relates to the pyrazole carboxylic acid analogues of Formula (1) or stereoisomers, or esters or pharmaceutically acceptable salts thereof, as potent anti- mycobacterial agents. Formula Further it discloses the pharmaceutical composition comprising compounds of Formula-I for the treatment of mycobacterial infections.

  本发明涉及Formula（1）的吡唑羧酸类似物或其立体异构体，或其酯或药用可接受的盐，作为有效的抗分枝杆菌药物。此外，还披露了包含Formula-I化合物的药物组合物，用于治疗分枝杆菌感染。
• Discovery of Rimonabant and its potential analogues as anti-TB drug candidates
  作者：J. M. Gajbhiye、N. A. More、Manoj D. Patil、R. Ummanni、S. S. Kotapalli、P. Yogeeswari、D. Sriram、V. H. Masand

  DOI：10.1007/s00044-015-1346-4

  日期：2015.7

  Rimonabant and its analogues have been synthesized in moderate to good yields using a simple synthetic route. All the newly synthesized compounds were subjected to in vitro screening against M. tuberculosis and M. smegmatis. The most potent analogue JMG-14 exhibits MIC value of 3.13 compared to 3.25 and 50 A mu g/ml for ethambutol and pyrazinamide, respectively. The molecular docking reveals that pyrazole ring, number and position of halogen atoms play a crucial role in deciding interactions with MTCYP-121. These findings open up a new avenue in the search of potent anti-TB drugs with rimonabant and its novel analogue JMG-14 as lead molecules.