468743-23-9Relevant articles and documents
Structure-activity relationships of pyrazole-4-carbodithioates as antibacterials against methicillin–resistant Staphylococcus aureus
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)
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.
One-pot multistep mechanochemical synthesis of fluorinated pyrazolones
Howard, Joseph L.,Nicholson, William,Sagatov, Yerbol,Browne, Duncan L.
supporting information, p. 1950 - 1956 (2017/09/27)
Solventless mechanochemical synthesis represents a technique with improved sustainability metrics compared to solvent-based processes. Herein, we describe a methodical process to run one solventless reaction directly into another through multistep mechanochemistry, effectively amplifying the solvent savings. The approach has to consider the solid form of the materials and compatibility of any auxiliary used. This has culminated in the development of a two-step, one-jar protocol for heterocycle formation and subsequent fluorination that has been successfully applied across a range of substrates, resulting in 12 difluorinated pyrazolones in moderate to excellent yields.
A convenient microwave-assisted propylphosphonic anhydride (T3P mediated one-pot pyrazolone synthesis
Desroses, Matthieu,Jacques-Cordonnier, Marie-Caroline,Llona-Minguez, Sabin,Jacques, Sylvain,Koolmeister, Tobias,Helleday, Thomas,Scobie, Martin
supporting information, p. 5879 - 5885 (2013/09/23)
This paper describes a facile, efficient, and clean synthesis of various pyrazolones by employing T3P as a catalyst and performing the reaction under microwave irradiation. This two-step, one-pot reaction proceeded readily and tolerated a variety of functional groups. A wide range of pyrazolone derivatives were obtained in good to excellent yields. A one-pot, two-step procedure for the synthesis of pyrazolones is presented. This method, which uses T3P and microwave irradiation, is particularly easy to carry out and offers a notable alternative to the strongly acidic conditions that are generally employed with other synthetic approaches. Copyright
