1,2,μ-trithio-dicarbonic acid diethylamide dimethylamide | 25080-38-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫基化合物
• 英文名称: 1,2,μ-trithio-dicarbonic acid diethylamide dimethylamide
• 英文别名: diethyl-1-carbothioic dimethylcarbamothioic thioanhydride；(Diaethyl-thiocarbamoyl)-(dimethyl-thiocarbamoyl)-sulfan；N,N-Diaethyl-N',N'-dimethyl-thiuramsulfid；1,2,μ-Trithio-dikohlensaeure-diaethylamid-dimethylamid；Thiodicarbonic diamide ([(H2N)C(S)]2S), N,N-diethyl-Na(2),Na(2)-dimethyl-；dimethylcarbamothioyl N,N-diethylcarbamodithioate
• CAS: 25080-38-0
• 化学式: C₈H₁₆N₂S₃
• 分子量: 236.426
• InChiKey: DZKWXODPHXGJDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  sodium N,N-diethyldithiocarbamate 、 二甲氨基硫代甲酰氯 以 乙腈 为溶剂， 以70%的产率得到1,2,μ-trithio-dicarbonic acid diethylamide dimethylamide
  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

• Preparation of Mixed Carbamic/Dithiocarbamic Anhydrides<i>via</i>Silyl Carbamates or Silyl Dithiocarbamates
  作者：Ferenc Kardon、Mária Mörtl、Gábor Magyarfalvi

  DOI：10.1080/00397910701693658

  日期：2008.1

  Abstract The reactions of silyl carbamates and silyl dithiocarbamates with different acid chlorides (carbamoyl/thiocarbamoyl chloride, chloroformates, etc.) have been studied. The obtained mixed anhydrides have different thermal stability.

  摘要 研究了甲硅烷基氨基甲酸酯和甲硅烷基二硫代氨基甲酸酯与不同酰氯（氨基甲酰/硫代氨基甲酰氯、氯甲酸酯等）的反应。得到的混合酸酐具有不同的热稳定性。
• Thiocyanic and dithiocarbamic anhydrides and the process of making the same
  申请人：MATIERES COLORANTES & PROD CHI

  公开号：US02139935A1

  公开（公告）日：1938-12-13
• GB460889
  申请人：——

  公开号：——

  公开（公告）日：——
• Preparation of thiuram monosulfides
  申请人：SHARPLES CHEMICALS INC

  公开号：US02524081A1

  公开（公告）日：1950-10-03
• 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.