(E)-2-((2-butyl-4-chloro-1-(3-(4-(o-tolyl)piperazin-1-yl)propyl)-1H-imidazol-5-yl)methylene)hydrazinecarbothioamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (E)-2-((2-butyl-4-chloro-1-(3-(4-(o-tolyl)piperazin-1-yl)propyl)-1H-imidazol-5-yl)methylene)hydrazinecarbothioamide
• 英文别名: [(E)-[2-butyl-5-chloro-3-[3-[4-(o-tolyl)piperazin-1-yl]propyl]imidazol-4-yl]methyleneamino]thiourea；[(E)-[2-butyl-5-chloro-3-[3-[4-(2-methylphenyl)piperazin-1-yl]propyl]imidazol-4-yl]methylideneamino]thiourea
• 化学式: C₂₃H₃₄ClN₇S
• 分子量: 476.089
• InChiKey: RUMGRKPMSVSKPI-YZSQISJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  咪唑醛 在 吡啶 、 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 乙醇 、 水 、 丙酮 、 乙腈 为溶剂， 反应 20.0h， 生成 (E)-2-((2-butyl-4-chloro-1-(3-(4-(o-tolyl)piperazin-1-yl)propyl)-1H-imidazol-5-yl)methylene)hydrazinecarbothioamide
  参考文献：
  名称：

  2-Butyl-4-chloroimidazole based substituted piperazine-thiosemicarbazone hybrids as potent inhibitors of Mycobacterium tuberculosis

  摘要：

  Here a series of 2-butyl-4-chloroimidazole based substituted piperazine-thiosemicarbazone hybrids were designed by combining three different pharmacophoric fragments in single molecular architecture. 2-Butyl-4-chloro-1-(3-(4-substituted)piperazin-1-yl)propyl)-1H-imidazole-5-carbaldehydes (4a-p) prepared by reacting carboxaldehyde 2 with N-alkyl piperazines 3a-p which were condensed with thiosemicarbazine to give desired compounds 5a-p in very good yields. Among all sixteen compounds screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB), two compounds (E)-2-((2-butyl-4-chloro-1-(3-(4-(o-tolyl)piperazin-1-yl)propyl)-1H-imidazol-5-yl)methylene)hydrazinecarbothioamide 5e and (E)-2-((2-butyl-4-chloro-1-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)-1H-imidazol-5-yl)methylene)hydrazinecarbothioamide 5f were found to be the most potent antitubercular agents (MIC: 3.13 mu g/mL) with low toxicity profile. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.084

文献信息

• 2-Butyl-4-chloroimidazole based substituted piperazine-thiosemicarbazone hybrids as potent inhibitors of Mycobacterium tuberculosis
  作者：Anvesh Jallapally、Dinesh Addla、Perumal Yogeeswari、Dharmarajan Sriram、Srinivas Kantevari

  DOI：10.1016/j.bmcl.2014.09.084

  日期：2014.12

  Here a series of 2-butyl-4-chloroimidazole based substituted piperazine-thiosemicarbazone hybrids were designed by combining three different pharmacophoric fragments in single molecular architecture. 2-Butyl-4-chloro-1-(3-(4-substituted)piperazin-1-yl)propyl)-1H-imidazole-5-carbaldehydes (4a-p) prepared by reacting carboxaldehyde 2 with N-alkyl piperazines 3a-p which were condensed with thiosemicarbazine to give desired compounds 5a-p in very good yields. Among all sixteen compounds screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB), two compounds (E)-2-((2-butyl-4-chloro-1-(3-(4-(o-tolyl)piperazin-1-yl)propyl)-1H-imidazol-5-yl)methylene)hydrazinecarbothioamide 5e and (E)-2-((2-butyl-4-chloro-1-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)-1H-imidazol-5-yl)methylene)hydrazinecarbothioamide 5f were found to be the most potent antitubercular agents (MIC: 3.13 mu g/mL) with low toxicity profile. (C) 2014 Elsevier Ltd. All rights reserved.