328110-42-5Relevant articles and documents
Design, synthesis and mode of action of some new 2-(4'-aminophenyl) benzothiazole derivatives as potent antimicrobial agents
Singh, Meenakshi,Kumar Singh, Sudhir,Gangwar, Mayank,Sellamuthu, Satheeshkumar,Nath, Gopal,Singh, Sushil K.
, p. 429 - 437 (2016/05/24)
Background: The rapid evolution of antibiotic resistance poses a serious threat to public health. The development of heterocyclic benzothiazole derivatives, as efficient and potential agents, has been the focus of antibacterial drug discovery. Objective: Present study attempts to evaluate the antibacterial activity and mechanism of action of novel 2-(4'- aminophenyl) benzothiazole derivatives. Methods: Antibacterial activity of novel benzothiazole derivatives was evaluated by agar disc diffusion method against a panel of susceptible Gram-positive and Gram-negative strains. The mechanism of action was explored by bactericidal kinetics, membrane depolarization, fluorescent assisted cell cytometry and DNA cleavage studies. Results: Our findings revealed that compounds A07a and A07b turned out to be the most potent analogues having minimum inhibitory concentration values in the range of 3.91-31.2 g/ml against Staphylococcus aureus, Salmonella typhi, Pseudomonas aeruginosa and Escherichia coli. The new benzothiazole derivatives displayed different modes of action as elucidated by the studies on intact bacterial cells and plasmid DNA. The structure activity relationship studies showed prominent activity of compound A07a containing oxime moiety on carbonyl carbon along with less bulky electron releasing and lipophillic group (methoxy and chloro) in phenyl ring at C2 position of 2-(4'-aminophenyl) benzothiazole ring system. Conclusion: The potent antibacterial activity of compounds (A07a and A07b) was mediated by membrane perturbing and intracellular mode of actions. These results further validate the use of these derivatives in the treatment of microbial diseases and provide scope for further research.
Design, synthesis and mode of action of novel 2-(4-aminophenyl)benzothiazole derivatives bearing semicarbazone and thiosemicarbazone moiety as potent antimicrobial agents
Singh, Meenakshi,Singh, Sudhir Kumar,Gangwar, Mayank,Nath, Gopal,Singh, Sushil K.
, p. 263 - 282 (2016/01/25)
A novel series of substituted benzothiazoles, bearing semicarbazone and thiosemicarbazone moieties, was designed, synthesized and evaluated for their antimicrobial activity and possible mode of action. Structures of the synthesized compounds were elucidated by 1H NMR, 13C NMR, IR and Mass spectral data. The results revealed that compounds SC06, SC09, TS05 and TS07 have potent antibacterial activity against both Gram-positive and Gram-negative strains. Compound TS05 displayed most potent activity with MIC values of 3.91, 7.81 and 1.56 μg/ml against S. aureus, E. coli and P. aeruginosa, respectively. The results from cytoplasmic membrane permeabilization assay, FACS study as well as DNA-binding assays, evaluated against clinically relevant pathogens S. aureus and E. coli, suggest membrane perturbing as well as intracellular mode of action of this class of compounds. In addition, hemolytic activity of the compounds was measured which indicated their low cytotoxicity.
Design, synthesis and mode of action of some benzothiazole derivatives bearing an amide moiety as antibacterial agents
Singh, Sushil K.,Singh, Meenakshi,Singh, Sudhir K.,Gangwar, Mayank,Nath, Gopal
, p. 19013 - 19023 (2014/05/20)
In this study ten benzothiazole derivatives bearing the amide moiety were designed, synthesized and evaluated for their antibacterial activity and possible mode of action. Structures of the synthesized compounds were elucidated by spectral data. Four different Gram-negative and two different Gram-positive bacterial strains were used in antibacterial activity tests. Among all the synthesised compounds, compound A07 displayed the most potent inhibitory activity with minimum inhibitory concentration (MIC) values of 15.6, 7.81, 15.6, 3.91 μg ml-1 against S. aureus, E. coli, S. typhi and K. pneumoniae respectively. Structure-activity relationship (SAR) studies revealed that electronic and lipophillic factors of the phenyl ring had a significant effect on the antimicrobial activity of the designed compounds. The benzothiazole bearing amide (A01-A10) series exhibited different modes of action based on aryl group substitution as revealed by studies on intact bacterial cells and plasmid DNA. The present study provides us two active compounds (A07 and A10) with a membrane perturbing mode of action, and an intracellular mode of action due to binding with DNA along with potent activity against clinically relevant pathogens E. coli and S. aureus.
