2-(1H-Benzoimidazol-2-ylsulfanyl)-1-{4-[2-(1H-benzoimidazol-2-ylsulfanyl)-acetyl]-piperazin-1-yl}-ethanone | 345987-82-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(1H-Benzoimidazol-2-ylsulfanyl)-1-{4-[2-(1H-benzoimidazol-2-ylsulfanyl)-acetyl]-piperazin-1-yl}-ethanone
• 英文别名: 2-(1H-benzimidazol-2-ylsulfanyl)-1-[4-[2-(1H-benzimidazol-2-ylsulfanyl)acetyl]piperazin-1-yl]ethanone
• CAS: 345987-82-8
• 化学式: C₂₂H₂₂N₆O₂S₂
• 分子量: 466.588
• InChiKey: OQUCRTJLOGTNPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  哌嗪 、 噻唑并[2,3-b]苯并咪唑-3(2H)-酮 以 乙醇 为溶剂， 反应 3.0h， 以48%的产率得到2-(1H-Benzoimidazol-2-ylsulfanyl)-1-{4-[2-(1H-benzoimidazol-2-ylsulfanyl)-acetyl]-piperazin-1-yl}-ethanone
  参考文献：
  名称：

  Antihelminthic activity of some newly synthesized 5(6)-(un)substituted-1H-benzimidazol-2-ylthioacetylpiperazine derivatives

  摘要：

  Piperazine derivatives of 5(6)-substituted-(1H-benzimidazol-2-ylthio)acetic acids were synthesized by using two methods and studied for antihelminthic activity.The antiparasitic screening showed that compounds 18-24 exhibited higher activity against Trichinella spiralis in vitro in comparison to methyl 5-(propylthio)-1H-benzimidazol-2-yl-carbamate (albendazole). Most active were compounds 2-({2-[4-(4-chlorophenyl)piperazin-1-yl]-2-oxoethyl}thio)-1H-benzimidazole 21 and 2-{[2-oxo-2-(4-benzhydrylpiperazin-1-yl)ethyl]thio}-5(6)-methyl-1(H)-benzimidazole 19 as well as 2-({2-[4-(4-chlorophenyl)piperazin-1-yl]-2-oxoethyl}thio)-5(6)-methyl-](H)-benzimidazole 23 with efficacy of 96.0%, 98.4% and 100%, respectively.The tested derivatives 15-19 and 20-23 were less active against Syphacia obvelata in vivo than albendazole and exhibited the same efficacy as piperazine, but in twice lower concentration. Compounds 2-({2-[4-(4-chlorophenyl)piperazin-1-yl]-2-oxoethyl}thio)-1H-benzimidazole 21, 1,4-bis[(5(6)-methyl-l(H)-benzimidazol-2-ylthio)acetyl]piperazine 17 and 2-({2-[4-(4-chlorophenyl)piperazin-1-yl]-2-oxoethyl)thio)-5(6)-methyl- 1(H)-benzimidazole 23 had higher efficacies of 73%, 76%, and 77%, respectively. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.07.005

文献信息

• Antihelminthic activity of some newly synthesized 5(6)-(un)substituted-1H-benzimidazol-2-ylthioacetylpiperazine derivatives
  作者：Anelia Ts. Mavrova、Kamelya K. Anichina、Dimitar I. Vuchev、Jordan A. Tsenov、Pavletta S. Denkova、Magdalena S. Kondeva、Mitka K. Micheva

  DOI：10.1016/j.ejmech.2006.07.005

  日期：2006.12

  Piperazine derivatives of 5(6)-substituted-(1H-benzimidazol-2-ylthio)acetic acids were synthesized by using two methods and studied for antihelminthic activity.The antiparasitic screening showed that compounds 18-24 exhibited higher activity against Trichinella spiralis in vitro in comparison to methyl 5-(propylthio)-1H-benzimidazol-2-yl-carbamate (albendazole). Most active were compounds 2-(2-[4-(4-chlorophenyl)piperazin-1-yl]-2-oxoethyl}thio)-1H-benzimidazole 21 and 2-[2-oxo-2-(4-benzhydrylpiperazin-1-yl)ethyl]thio}-5(6)-methyl-1(H)-benzimidazole 19 as well as 2-(2-[4-(4-chlorophenyl)piperazin-1-yl]-2-oxoethyl}thio)-5(6)-methyl-](H)-benzimidazole 23 with efficacy of 96.0%, 98.4% and 100%, respectively.The tested derivatives 15-19 and 20-23 were less active against Syphacia obvelata in vivo than albendazole and exhibited the same efficacy as piperazine, but in twice lower concentration. Compounds 2-(2-[4-(4-chlorophenyl)piperazin-1-yl]-2-oxoethyl}thio)-1H-benzimidazole 21, 1,4-bis[(5(6)-methyl-l(H)-benzimidazol-2-ylthio)acetyl]piperazine 17 and 2-(2-[4-(4-chlorophenyl)piperazin-1-yl]-2-oxoethyl)thio)-5(6)-methyl- 1(H)-benzimidazole 23 had higher efficacies of 73%, 76%, and 77%, respectively. (c) 2006 Elsevier Masson SAS. All rights reserved.