N-phenethyl-4-(3-hydroxy-3-phenylpropyl)piperazine-1-carbothioamide

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-phenethyl-4-(3-hydroxy-3-phenylpropyl)piperazine-1-carbothioamide
• 英文别名: 4-(3-hydroxy-3-phenylpropyl)-N-(2-phenylethyl)piperazine-1-carbothioamide
• 化学式: C₂₂H₂₉N₃OS
• 分子量: 383.558
• InChiKey: YCIVWVOODWDTDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  70.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-phenethyl-4-(3-hydroxy-3-phenylpropyl)piperazine-1-carbothioamide 、 对氯三氟甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以61%的产率得到phenethyl 4-(3-phenyl-3-(4-(trifluoromethyl)phenoxy)propyl)-piperazine-1-carbothioamide
  参考文献：
  名称：

  N-Alkyl/aryl-4-(3-substituted-3-phenylpropyl)piperazine-1-carbothioamide as dual-action vaginal microbicides with reverse transcriptase inhibition

  摘要：

  The growing population and health-care burden (due to STIs and HIV) imposes a particular economic crisis over resource-poor countries. Thus a novel approach as vaginal microbicides emerges as integrated tool to control both population and anti-STIs/HIV. Our continued efforts in this field led to the synthesis of fifteen N-alkyl/aryl-4-(3-substituted-3-phenylpropyl) piperazine-l-carbothioamide (12-26) derivatives as topical vaginal microbicides which were evaluated for anti-Trichomonas, spermicidal, antifungal and reverse transcriptase (RT) inhibitory activities. All compounds were also tested for preliminary safety through cytotoxicity assays against human cervical cell line (HeLa) and the vaginal flora, Lactobacillus. Docking studies were performed to gain an insight into the binding mode and interactions of the most promising compound 12 [oxo derivative], comprising of reverse transcriptase (RT) inhibitory (72.30%), spermicidal (MEC 0.01%), anti-Trithomonas (MIC 46.72 mu M) and antifimgal (MIC 9.34 -74.8 mu M) activities, along with its hydroxyl (17) and O-alkylated 4-trifluoromethylphenoxy (22) derivative, with similar activities. The stability of compound 12 in simulated vaginal fluid (SVF) and its preliminary in vivo pharmacokinetics performed in female NZ-rabbits signifies its clinical safety in comparison to marketed spermicide Nonoxynol-9. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.021
• 作为产物：
  描述：

  2-苯基乙基异硫代氰酸酯 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.0h， 生成 N-phenethyl-4-(3-hydroxy-3-phenylpropyl)piperazine-1-carbothioamide
  参考文献：
  名称：

  N-Alkyl/aryl-4-(3-substituted-3-phenylpropyl)piperazine-1-carbothioamide as dual-action vaginal microbicides with reverse transcriptase inhibition

  摘要：

  The growing population and health-care burden (due to STIs and HIV) imposes a particular economic crisis over resource-poor countries. Thus a novel approach as vaginal microbicides emerges as integrated tool to control both population and anti-STIs/HIV. Our continued efforts in this field led to the synthesis of fifteen N-alkyl/aryl-4-(3-substituted-3-phenylpropyl) piperazine-l-carbothioamide (12-26) derivatives as topical vaginal microbicides which were evaluated for anti-Trichomonas, spermicidal, antifungal and reverse transcriptase (RT) inhibitory activities. All compounds were also tested for preliminary safety through cytotoxicity assays against human cervical cell line (HeLa) and the vaginal flora, Lactobacillus. Docking studies were performed to gain an insight into the binding mode and interactions of the most promising compound 12 [oxo derivative], comprising of reverse transcriptase (RT) inhibitory (72.30%), spermicidal (MEC 0.01%), anti-Trithomonas (MIC 46.72 mu M) and antifimgal (MIC 9.34 -74.8 mu M) activities, along with its hydroxyl (17) and O-alkylated 4-trifluoromethylphenoxy (22) derivative, with similar activities. The stability of compound 12 in simulated vaginal fluid (SVF) and its preliminary in vivo pharmacokinetics performed in female NZ-rabbits signifies its clinical safety in comparison to marketed spermicide Nonoxynol-9. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.021