Design and synthesis of some new 1,3,4-thiadiazines with coumarin moieties and their antioxidative and antifungal activity.
A series of newly disubstituted (compounds 4a,b) and trisubstituted 1,3,4-thiadiazines 5a-l with various substituents was prepared utilizing different thiosemicarbazides and 3-α-bromoacetylcoumarins as starting compounds. The structures of the synthesized 1,3,4-thiadiazines are elucidated and confirmed utilizing the corresponding analytical and spectroscopic data. All of the new thiadiazine derivatives were tested for their antioxidant activity, employing different antioxidant assays (DPPH scavenging activity, iron chelating activity, power reducing activity). Compounds 5b, 5f, 5j and 4b were proven to be the best DPPH radical scavengers, while compounds 5h and 5j have shown the best iron chelating activity. Thiadiazine derivatives were also tested on their antifungal activity against four mycotoxicogenic fungi, Aspergillus flavus, A. ochraceus, Fusarium graminearum and F. verticillioides. The best antifungal against A. flavus was proven to be compound 5e, while compounds 4a and 5c were the best antifungals on A. ochraceus, and compound 5g showed the best antifungal activity on F. verticillioides.
Department of Applied Chemistry and Ecology, Faculty of Food Technology, J. J. Strossmayer University, Franje Kuhača 20, Osijek 31 000, Croatia. mcacic@ptfos.hr.
Milan
M
Cačić
Department of Applied Chemistry and Ecology, Faculty of Food Technology, J. J. Strossmayer University, Franje Kuhača 20, Osijek 31 000, Croatia. valentina.pavic@biologija.unios.hr.
Valentina
V
Pavić
Department of Applied Chemistry and Ecology, Faculty of Food Technology, J. J. Strossmayer University, Franje Kuhača 20, Osijek 31 000, Croatia. maja.molnar@ptfos.hr.
Maja
M
Molnar
Department of Applied Chemistry and Ecology, Faculty of Food Technology, J. J. Strossmayer University, Franje Kuhača 20, Osijek 31 000, Croatia. bojan.sarkanj@ptfos.hr.
Bojan
B
Sarkanj
Department of Applied Chemistry and Ecology, Faculty of Food Technology, J. J. Strossmayer University, Franje Kuhača 20, Osijek 31 000, Croatia. hasschon@biologija.unios.hr.
Elizabeta
E
Has-Schön
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001231:Aspergillus flavus / Q000187:drug effects; D001713:Biphenyl Compounds / Q000737:chemistry; D003374:Coumarins / Q000138:chemical synthesis* / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000494:pharmacology; D005609:Free Radicals / Q000737:chemistry; D005670:Fusarium / Q000187:drug effects; D007502:Iron Chelating Agents / Q000138:chemical synthesis / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D010084:Oxidation-Reduction; D010851:Picrates / Q000737:chemistry; D012663:Semicarbazides / Q000737:chemistry; D013829:Thiadiazines / Q000138:chemical synthesis* / Q000494:pharmacology
D000935:Antifungal Agents; D001713:Biphenyl Compounds; D003374:Coumarins; D016166:Free Radical Scavengers; D005609:Free Radicals; D007502:Iron Chelating Agents; D010851:Picrates; D012663:Semicarbazides; D013829:Thiadiazines; C004931:1,1-diphenyl-2-picrylhydrazyl