4-(ethylthiocarbonothioyl)piperazine-1-carbothioic dimethylcarbamothioic thioanhydride

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 二硫代氨基甲酸及其衍生物
• 英文名称: 4-(ethylthiocarbonothioyl)piperazine-1-carbothioic dimethylcarbamothioic thioanhydride
• 英文别名: 4-S-(dimethylcarbamothioyl) 1-S-ethyl piperazine-1,4-dicarbodithioate
• 化学式: C₁₁H₁₉N₃S₅
• 分子量: 353.622
• InChiKey: SMKZVMIGJASPHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  157
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙基1-哌嗪二硫代甲酸酯 在 sodium hydroxide 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 0.5h， 生成 4-(ethylthiocarbonothioyl)piperazine-1-carbothioic dimethylcarbamothioic thioanhydride
  参考文献：
  名称：

  Substituted carbamothioic amine-1-carbothioic thioanhydrides as novel trichomonicidal fungicides: Design, synthesis, and biology

  摘要：

  Sexually transmitted diseases like trichomoniasis along with opportunistic fungal infections like candidiasis are major global health burden in female reproductive health. In this context a novel non-nitroimidazole class of substituted carbamothioic amine-1-carbothioic thioanhydride series was designed, synthesized, evaluated for trichomonacidal and fungicidal activities, and was found to be more active than the standard drug Metronidazole (MTZ). Compounds were trichomonicidal in the MIC ranges of 4.77-294.1 mu M and 32.46-735.20 mu M against MTZ-susceptible and-resistant strains, respectively. Further, compounds inhibited the growth of at least two out of ten fungal strains tested at MIC of 7.50 -240.38 mu M. The most active compound (20) of this series was 3.8 and 9.5 fold more active than the MTZ against the two Trichomonas strains tested. Compound 20 also significantly inhibited the sulfhydryl groups present over Trichomonas vaginalis and was found to be more active than the MTZ in vivo. Further, a docking analysis carried out with cysteine proteases supported their thiol inhibiting ability and preliminary pharmacokinetic study has shown good distribution and systemic clearance. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.060

文献信息

• Substituted carbamothioic amine-1-carbothioic thioanhydrides as novel trichomonicidal fungicides: Design, synthesis, and biology
  作者：Dhanaraju Mandalapu、Bhavana Kushwaha、Sonal Gupta、Shagun Krishna、Nidhi Srivastava、Mahendra Shukla、Pratiksha Singh、Bhavana S. Chauhan、Ravi Goyani、Jagdamba P. Maikhuri、Koneni V. Sashidhara、Brijesh Kumar、Renu Tripathi、Praveen K. Shukla、Mohammad I. Siddiqi、Jawahar Lal、Gopal Gupta、Vishnu L. Sharma

  DOI：10.1016/j.ejmech.2017.11.060

  日期：2018.1

  Sexually transmitted diseases like trichomoniasis along with opportunistic fungal infections like candidiasis are major global health burden in female reproductive health. In this context a novel non-nitroimidazole class of substituted carbamothioic amine-1-carbothioic thioanhydride series was designed, synthesized, evaluated for trichomonacidal and fungicidal activities, and was found to be more active than the standard drug Metronidazole (MTZ). Compounds were trichomonicidal in the MIC ranges of 4.77-294.1 mu M and 32.46-735.20 mu M against MTZ-susceptible and-resistant strains, respectively. Further, compounds inhibited the growth of at least two out of ten fungal strains tested at MIC of 7.50 -240.38 mu M. The most active compound (20) of this series was 3.8 and 9.5 fold more active than the MTZ against the two Trichomonas strains tested. Compound 20 also significantly inhibited the sulfhydryl groups present over Trichomonas vaginalis and was found to be more active than the MTZ in vivo. Further, a docking analysis carried out with cysteine proteases supported their thiol inhibiting ability and preliminary pharmacokinetic study has shown good distribution and systemic clearance. (C) 2017 Elsevier Masson SAS. All rights reserved.