2-chloro-1-(4-(3,4-dichlorobenzyl)piperazin-1-yl)ethanone | 1220348-76-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-chloro-1-(4-(3,4-dichlorobenzyl)piperazin-1-yl)ethanone
• 英文别名: 1-chloroacetyl-4-(3,4-dichlorobenzyl)piperazine；2-Chloro-1-[4-[(3,4-dichlorophenyl)methyl]piperazin-1-yl]ethanone
• CAS: 1220348-76-4
• 化学式: C₁₃H₁₅Cl₃N₂O
• 分子量: 321.634
• InChiKey: ZUGHWNIMLLRBNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-1-(4-(3,4-dichlorobenzyl)piperazin-1-yl)ethanone 、 3-硝基-1,2,4-三氮唑 在 potassium hydroxide 作用下， 以 乙腈 为溶剂， 反应 9.5h， 以88%的产率得到1-(4-(3,4-dichlorobenzyl)piperazin-1-yl)-2-(3-nitro-1H-1,2,4-triazol-1-yl)ethanone
  参考文献：
  名称：

  3-Nitrotriazole-based piperazides as potent antitrypanosomal agents

  摘要：

  Novel linear 3-nitro-1H-1,2,4-triazole-based piperazides were synthesized and evaluated as anti-trypanosomal agents. In addition, some bisarylpiperazine-ethanones which were formed as by-products were also screened for antiparasitic activity. Most 3-nitrotriazole-based derivatives were potent and selective against Trypanosoma cruzi parasites, but only one displayed these desired properties against Trypanosoma brucei rhodesiense. Moreover, two 3-nitrotriazole-based chlorophenylpiperazides were moderately and selectively active against Leishmania donovani. Although the bisarylpiperazineethanones were active or moderately active against I cruzi, none of them demonstrated an acceptable selectivity. In general, 3-nitrotriazole-based piperazides were less toxic to host L6 cells than the previously evaluated 3-nitrotriazole-based piperazines and seven of 13 were 1.54- to 31.2-fold more potent antichagasic agents than the reference drug benznidazole. Selected compounds showed good ADMET characteristics. One potent in vitro antichagasic compound (3) was tested in an acute murine model and demonstrated antichagasic activity after a 10-day treatment of 15 mg/kg/day. However, neither compound 3 nor benznidazole showed a statistically significant P value compared to control due to high variability in parasite burden among the untreated animals. Working as prodrugs, 3-nitrotriazole-based piperazides were excellent substrates of trypanosomal type I nitroreductases and constitute a novel class of potentially effective and more affordable antitrypanosomal agents. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.08.042
• 作为产物：
  描述：

  1-(3,4-二氯苄基)哌嗪 、 氯乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到2-chloro-1-(4-(3,4-dichlorobenzyl)piperazin-1-yl)ethanone
  参考文献：
  名称：

  3-Nitrotriazole-based piperazides as potent antitrypanosomal agents

  摘要：

  Novel linear 3-nitro-1H-1,2,4-triazole-based piperazides were synthesized and evaluated as anti-trypanosomal agents. In addition, some bisarylpiperazine-ethanones which were formed as by-products were also screened for antiparasitic activity. Most 3-nitrotriazole-based derivatives were potent and selective against Trypanosoma cruzi parasites, but only one displayed these desired properties against Trypanosoma brucei rhodesiense. Moreover, two 3-nitrotriazole-based chlorophenylpiperazides were moderately and selectively active against Leishmania donovani. Although the bisarylpiperazineethanones were active or moderately active against I cruzi, none of them demonstrated an acceptable selectivity. In general, 3-nitrotriazole-based piperazides were less toxic to host L6 cells than the previously evaluated 3-nitrotriazole-based piperazines and seven of 13 were 1.54- to 31.2-fold more potent antichagasic agents than the reference drug benznidazole. Selected compounds showed good ADMET characteristics. One potent in vitro antichagasic compound (3) was tested in an acute murine model and demonstrated antichagasic activity after a 10-day treatment of 15 mg/kg/day. However, neither compound 3 nor benznidazole showed a statistically significant P value compared to control due to high variability in parasite burden among the untreated animals. Working as prodrugs, 3-nitrotriazole-based piperazides were excellent substrates of trypanosomal type I nitroreductases and constitute a novel class of potentially effective and more affordable antitrypanosomal agents. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.08.042

文献信息

• NOVEL PYRAZOLYLMETHYLAMINE COMPOUNDS AS CALCIUM CHANNEL MODULATORS AND PREPARATION METHOD THEREOF
  申请人：NAM Ghilsoo

  公开号：US20100094006A1

  公开（公告）日：2010-04-15

  The present invention relates to pyrazolylmethylamine-piperazine derivatives and their pharmaceutically acceptable salts effective as calcium channel modulators and a method of manufacturing the same. The present invention also relates to the medicinal use of the above compounds as therapeutic treatment of diseases due to their effect as calcium channel modulators.

  本发明涉及吡唑甲基胺基哌嗪衍生物及其药用盐，其作为钙通道调节剂具有有效性，以及其制造方法。本发明还涉及上述化合物的药用作用，用于治疗因其作为钙通道调节剂而产生的疾病。
• US8299072B2
  申请人：——

  公开号：US8299072B2

  公开（公告）日：2012-10-30
• 3-Nitrotriazole-based piperazides as potent antitrypanosomal agents
  作者：Maria V. Papadopoulou、William D. Bloomer、Howard S. Rosenzweig、Ivan P. O'Shea、Shane R. Wilkinson、Marcel Kaiser

  DOI：10.1016/j.ejmech.2015.08.042

  日期：2015.10

  Novel linear 3-nitro-1H-1,2,4-triazole-based piperazides were synthesized and evaluated as anti-trypanosomal agents. In addition, some bisarylpiperazine-ethanones which were formed as by-products were also screened for antiparasitic activity. Most 3-nitrotriazole-based derivatives were potent and selective against Trypanosoma cruzi parasites, but only one displayed these desired properties against Trypanosoma brucei rhodesiense. Moreover, two 3-nitrotriazole-based chlorophenylpiperazides were moderately and selectively active against Leishmania donovani. Although the bisarylpiperazineethanones were active or moderately active against I cruzi, none of them demonstrated an acceptable selectivity. In general, 3-nitrotriazole-based piperazides were less toxic to host L6 cells than the previously evaluated 3-nitrotriazole-based piperazines and seven of 13 were 1.54- to 31.2-fold more potent antichagasic agents than the reference drug benznidazole. Selected compounds showed good ADMET characteristics. One potent in vitro antichagasic compound (3) was tested in an acute murine model and demonstrated antichagasic activity after a 10-day treatment of 15 mg/kg/day. However, neither compound 3 nor benznidazole showed a statistically significant P value compared to control due to high variability in parasite burden among the untreated animals. Working as prodrugs, 3-nitrotriazole-based piperazides were excellent substrates of trypanosomal type I nitroreductases and constitute a novel class of potentially effective and more affordable antitrypanosomal agents. (C) 2015 Elsevier Masson SAS. All rights reserved.