benzyl 4-(phenethylcarbamothioyl)piperazine-1-carbodithioate

• 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: benzyl 4-(phenethylcarbamothioyl)piperazine-1-carbodithioate
• 英文别名: Benzyl 4-(phenethylcarbamothioyl)piperazine-1-carbodithioate；benzyl 4-(2-phenylethylcarbamothioyl)piperazine-1-carbodithioate
• 化学式: C₂₁H₂₅N₃S₃
• 分子量: 415.648
• InChiKey: MCEUGBPTPKRAJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  tert-butyl 4-(benzylthiocarbonothioyl)piperazine-1-carboxylate 在 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 benzyl 4-(phenethylcarbamothioyl)piperazine-1-carbodithioate
  参考文献：
  名称：

  Dithiocarbamate–thiourea hybrids useful as vaginal microbicides also show reverse transcriptase inhibition: Design, synthesis, docking and pharmacokinetic studies

  摘要：

  Prophylactic prevention is considered as the most promising strategy to tackle STI/HIV. Twenty-five dithiocarbamate-thiourea hybrids (14-38) were synthesized as woman controlled topical vaginal microbicides to counter Trichomonas vaginalis and sperm along with RT inhibition potential. The four promising compounds (18, 26, 28 and 33) were tested for safety through cytotoxic assay against human cervical cell line (HeLa) and compatibility with vaginal flora, Lactobacillus. Docking study of most promising vaginal microbicide (33) revealed that it docked in a position and orientation similar to known reverse transcriptase inhibitor Nevirapine. The preliminary in vivo pharmacokinetics of compound 33 was performed in NZ-rabbits to evaluate systemic toxicity in comparison to Nonoxynol-9. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.062

文献信息

• Dithiocarbamate–thiourea hybrids useful as vaginal microbicides also show reverse transcriptase inhibition: Design, synthesis, docking and pharmacokinetic studies
  作者：Veenu Bala、Santosh Jangir、Dhanaraju Mandalapu、Sonal Gupta、Yashpal S. Chhonker、Nand Lal、Bhavana Kushwaha、Hardik Chandasana、Shagun Krishna、Kavita Rawat、Jagdamba P. Maikhuri、Rabi S. Bhatta、Mohammad I. Siddiqi、Rajkamal Tripathi、Gopal Gupta、Vishnu L. Sharma

  DOI：10.1016/j.bmcl.2014.12.062

  日期：2015.2

  Prophylactic prevention is considered as the most promising strategy to tackle STI/HIV. Twenty-five dithiocarbamate-thiourea hybrids (14-38) were synthesized as woman controlled topical vaginal microbicides to counter Trichomonas vaginalis and sperm along with RT inhibition potential. The four promising compounds (18, 26, 28 and 33) were tested for safety through cytotoxic assay against human cervical cell line (HeLa) and compatibility with vaginal flora, Lactobacillus. Docking study of most promising vaginal microbicide (33) revealed that it docked in a position and orientation similar to known reverse transcriptase inhibitor Nevirapine. The preliminary in vivo pharmacokinetics of compound 33 was performed in NZ-rabbits to evaluate systemic toxicity in comparison to Nonoxynol-9. (C) 2014 Elsevier Ltd. All rights reserved.