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Synthesis and Antibacterial Activity of Novel Fused 1,3‐Thiazoles and 1,3‐Thiazines Incorporating a 2,4‐Dihydroxyphenyl Residue
Author(s) -
Matysiak Joanna,
Los Renata,
Malm Anna,
Karpińska Monika M.,
Głaszcz Urszula,
Rajtar Barbara,
PolzDacewicz Małgorzata,
TrojanowskaWesołowska Marta,
Niewiadomy Andrzej
Publication year - 2012
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201100251
Subject(s) - moiety , thiazole , chemistry , antimicrobial , antibacterial activity , reagent , combinatorial chemistry , cytotoxicity , stereochemistry , residue (chemistry) , aryl , minimum inhibitory concentration , chemical synthesis , organic chemistry , bacteria , in vitro , biochemistry , biology , alkyl , genetics
In an attempt to find a new class of antimicrobial agents, a series of benzothiazoles, 1,3‐thiazolo[5,4‐ b ]pyridines, 4 H ‐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‐4 H ‐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.