Design and Synthesis of Some New 1,3,4-Thiadiazines with Coumarin Moieties and Their Antioxidative and Antifungal Activity

被引：34
作者：
Cacic, Milan [1 ]
Pavic, Valentina [2 ]
Molnar, Maja [1 ]
Sarkanj, Bojan [1 ]
Has-Schoen, Elizabeta [2 ]
机构：
[1] JJ Strossmayer Univ, Fac Food Technol, Dept Appl Chem & Ecol, Osijek 31000, Croatia
[2] JJ Strossmayer Univ, Dept Biol, Osijek 31000, Croatia
来源：
MOLECULES | 2014年 / 19卷 / 01期
关键词：
coumarin; 1,3,4-thiadiazines; thiosemicarbazides; antifungal activity; antioxidative activity; PECHMANN REACTION; DERIVATIVES; ACIDS;
D O I：
10.3390/molecules19011163
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
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-alpha-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.
引用
收藏
页码：1163 / 1177
页数：15
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