November 2017 Convenient Synthesis and Biological Activity of Mono and Diacyl 2,5-Dimercapto-1,3,4-thiadiazole Derivatives

被引:2
|
作者
Jasiak, Karolina [1 ]
Kudelko, Agnieszka [1 ]
Wroblowska, Monika [1 ]
Biernasiuk, Anna [2 ]
Malm, Anna [2 ]
Krawczyk, Maria [3 ]
机构
[1] Silesian Tech Univ, Dept Chem Organ Technol & Petrochem, Krzywoustego 4, PL-44100 Gliwice, Poland
[2] Med Univ, Fac Pharm, Dept Pharmaceut Microbiol, Chodzki 1, PL-20093 Lublin, Poland
[3] Inst Ind Organ Chem, Annopol 6, PL-03236 Warsaw, Poland
关键词
ANTIMICROBIAL ACTIVITY; ANTIFUNGAL ACTIVITY; 1,3,4-THIADIAZOLES;
D O I
10.1002/jhet.2942
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New derivatives of 2,5-dimercapto-1,3,4-thiadiazole substituted both at one or two exocyclic sulfur atoms with a series of aroyl or ethoxycarbonyl groups were synthesized in reactions of 2,5-dimercapto-1,3,4-thiadiazole salts with appropriate acid chlorides or ethyl chloroformate in mild conditions. The products were characterized by spectroscopy (H-1 NMR, C-13 NMR, IR, and HRMS). Some from the synthesized compounds were screened in vitro and in vivo for antibacterial and antifungal activities against a panel of reference strains of microorganisms. The study revealed that ethyl S-(5-mercapto-1,3,4-thiadiazol-2-y1) carbonothioate seems to he the most active and versatile compound against Gram-positive bacteria, Gram-negative bacteria, and plant pathogenic fungi.
引用
收藏
页码:3241 / 3249
页数:9
相关论文
共 50 条
  • [31] Spectroscopic identification of 2,5-dimercapto-1,3,4-thiadiazole and its lithium salt and dimer forms
    Pope, John M.
    Sato, Toshitada
    Shoji, Eiichi
    Buttry, Daniel A.
    Sotomura, Tadashi
    Oyama, Noboru
    Journal of Power Sources, 1997, 68 (2 pt 2): : 739 - 742
  • [32] 2,5-Dimercapto-1,3,4-Thiadiazole(DMCT)-Based Polymers for Rechargeable Metal–Sulfur Batteries
    Amruth Bhargav
    Arumugam Manthiram
    Energy & Environmental Materials, 2023, 6 (06) : 287 - 294
  • [33] Chemical reactions of 2,5-dimercapto-1,3,4-thiadiazole (DMTD) with metallic copper, silver, and mercury
    Huang, L
    Tang, F
    Hu, BX
    Shen, J
    Yu, T
    Meng, QJ
    JOURNAL OF PHYSICAL CHEMISTRY B, 2001, 105 (33): : 7984 - 7989
  • [34] The synthesis, characterization, and DC electrical conductivity of poly[di(2,5-dimercapto-1,3,4-thiadiazole)-metal] complexes
    El-Shekeil, Ali G.
    Al-Maydama, Hussein M.
    Al-Shuja's, Omar M.
    JOURNAL OF APPLIED POLYMER SCIENCE, 2007, 106 (04) : 2427 - 2435
  • [35] Soluble 2,5-dimercapto-1,3,4-thiadiazole/poly(o-toluidine) electroactive composite
    Yu, L
    Wang, XH
    Li, J
    Jing, XB
    Wang, FS
    JOURNAL OF THE ELECTROCHEMICAL SOCIETY, 1999, 146 (05) : 1712 - 1716
  • [36] Evaluation of Schiff bases of 2,5-dimercapto-1,3,4-thiadiazole as photostabilizer for poly(methyl methacrylate)
    Yousif, Emad
    Bakir, Emaad
    Salimon, Jumat
    Salih, Nadia
    JOURNAL OF SAUDI CHEMICAL SOCIETY, 2012, 16 (03) : 279 - 285
  • [37] Sorption and preconcentration of metal ions on silica gel modified with 2,5-dimercapto-1,3,4-thiadiazole
    Lessi, P
    Dias, NL
    Moreira, JC
    Campos, JTS
    ANALYTICA CHIMICA ACTA, 1996, 327 (02) : 183 - 190
  • [38] The adsorption of 2,5-dimercapto-1,3,4-thiadiazole (DMTD) on copper surface and its binding behavior
    Huang, L
    Shen, J
    Ren, J
    Meng, QJ
    Yu, T
    CHINESE SCIENCE BULLETIN, 2001, 46 (05): : 387 - 390
  • [39] Spectroscopic identification of 2,5-dimercapto-1,3,4-thiadiazole and its lithium salt and dimer forms
    Pope, JM
    Sato, T
    Shoji, E
    Buttry, DA
    Sotomura, T
    Oyama, N
    JOURNAL OF POWER SOURCES, 1997, 68 (02) : 739 - 742
  • [40] The nature of the interaction between polyaniline and 2,5-dimercapto-1,3,4-thiadiazole in electrochemical redox processes
    Wang, P
    JOURNAL OF THE ELECTROCHEMICAL SOCIETY, 2002, 149 (09) : A1171 - A1174