Synthesis and antibacterial activity of novel fused 1,3-thiazoles and 1,3-thiazines incorporating a 2,4-dihydroxyphenyl residue.
In an attempt to find a new class of antimicrobial agents, a series of benzothiazoles, 1,3-thiazolo[5,4-b]pyridines, 4H-3,1-benzothiazines, naphtho[2,3-d][1,3]thiazole-4,9-diones and other related compounds containing a 2,4-dihydroxyphenyl moiety were prepared. They were obtained via the reaction of aryl-modified sulfinyl[bis(2,4-dihydroxyphenylmethanethione)]s with appropriate commercial chemical reagents in the endocyclization processes. The MIC values of the compounds towards eight reference bacterial strains were assessed by the two-fold serial micro-dilution broth method. They exhibited inhibitory effects against the Gram-positive strains tested opposite to Gram-negative ones. Some compounds were more effective than the reference drug. 4-(6-Chloro-4H-3,1-benzothiazin-2-yl)-6-methylbenzene-1,3-diol (5b) due to its very good activity (MIC from 1.56 to 3.13 µg/mL) and low cytotoxicity (IC(50) > 50 µg/mL) may be regarded as a promising precursor for the development of novel antibacterial agents.
Department of Chemistry, University of Life Sciences, Lublin, Poland. joanna.matysiak@up.lublin.pl
Joanna
J
Matysiak
Renata
R
Los
Anna
A
Malm
Monika M
MM
Karpińska
Urszula
U
Głaszcz
Barbara
B
Rajtar
Małgorzata
M
Polz-Dacewicz
Marta
M
Trojanowska-Wesołowska
Andrzej
A
Niewiadomy
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests / Q000379:methods / Q000706:statistics & numerical data; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013843:Thiazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000890:Anti-Infective Agents; D013843:Thiazines; D013844:Thiazoles