Structure-activity relationships of pyrazole-4-carbodithioates as antibacterials against methicillin–resistant Staphylococcus aureus
Methicillin-resistant Staphylococcus aureus (MRSA) is a major cause of serious hospital-acquired infections and is responsible for significant morbidity and mortality in residential care facilities. New agents against MRSA are needed to combat rising resistance to current antibiotics. We recently reported 5-hydroxy-3-methyl-1-phenyl-1H-pyrazole-4-carbodithioate (HMPC) as a new bacteriostatic agent against MRSA that appears to act via a novel mechanism. Here, twenty nine analogs of HMPC were synthesized, their anti-MRSA structure-activity relationships evaluated and selectivity versus human HKC-8 cells determined. Minimum inhibitory concentrations (MIC) ranged from 0.5 to 64 μg/mL and up to 16-fold selectivity was achieved. The 4-carbodithioate function was found to be essential for activity but non-specific reactivity was ruled out as a contributor to antibacterial action. The study supports further work aimed at elucidating the molecular targets of this interesting new class of anti-MRSA agents.
Majed, Hiwa,Johnston, Tatiana,Kelso, Celine,Monachino, Enrico,Jergic, Slobodan,Dixon, Nicholas E.,Mylonakis, Eleftherios,Kelso, Michael J.
supporting information
p. 3526 - 3528
(2018/10/15)
Palladium-catalyzed carbonylative coupling of α-chloroketones with hydrazines: a simple route to pyrazolone derivatives
A range of pyrazol-5-one and pyrazol-3-one derivatives has been synthesized in a single step via a palladium-catalyzed carbonylation of aromatic or aliphatic α-chloroketones, in the presence of aromatic or aliphatic hydrazines. A reaction mechanism, explaining the observed regioselectivity, has been also discussed.
Base initiated aromatization/CO bond formation: A new entry to O-pyrazole polyfluoroarylated ethers
A base initiated intermolecular SNAr reaction of pyrazolones with polyfluoroarenes was developed. The process involved the isomerization aromatization of pyrazolone followed by the CO bond formation via the selective CF bond cleavage. With this strategy, a wide range of O-pyrazole polyfluoroarylated ethers bearing diverse functional groups were synthesized in mild to good yields. Additionally, our method was also applied to the isoxazol substrates.
Tang, Xiangyang,Chang, Jing,Liu, Cuibo,Zhang, Bin
p. 6534 - 6537
(2015/01/08)
A New Synthesis of 2-Pyrazolin-5-ones from the Condensation of C(α),N-Dilithiophenylhydrazones with Diethyl Carbonate
C(α),N-Dilithiophenylhydrazones were prepared from phenylhydrazones in an excess of lithium diisopropylamide and condensed with diethyl carbonate followed dy an acid cyclization to give 2-pyrazolin-5-ones.
Wilson, Jana D.,Fulmer, Tammy D.,Dasher, Lisette P.,Beam, Charles F.
p. 389 - 391
(2007/10/02)
Halogen pyrazoles derivatives, a method for producing these halogen pyrazole derivatives and medicaments containing them
1,3-Diaryl-5-halogen-pyrazole-4-acetic acids and their derivatives with analgetic, antipyretic and antiphlogistic action are described.
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(2008/06/13)
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