51138-46-6Relevant articles and documents
Decoupling Activation of Heme Biosynthesis from Anaerobic Toxicity in a Molecule Active in Staphylococcus aureus
Dutter, Brendan F.,Mike, Laura A.,Reid, Paul R.,Chong, Katherine M.,Ramos-Hunter, Susan J.,Skaar, Eric P.,Sulikowski, Gary A.
, p. 1354 - 1361 (2016/06/09)
Small molecules active in the pathogenic bacterium Staphylococcus aureus are valuable tools for the study of its basic biology and pathogenesis, and many molecules may provide leads for novel therapeutics. We have previously reported a small molecule, 1, which activates endogenous heme biosynthesis in S. aureus, leading to an accumulation of intracellular heme. In addition to this novel activity, 1 also exhibits toxicity towards S. aureus growing under fermentative conditions. To determine if these activities are linked and establish what features of the molecule are required for activity, we synthesized a library of analogs around the structure of 1 and screened them for activation of heme biosynthesis and anaerobic toxicity to investigate structure-activity relationships. The results of this analysis suggest that these activities are not linked. Furthermore, we have identified the structural features that promote each activity and have established two classes of molecules: activators of heme biosynthesis and inhibitors of anaerobic growth. These molecules will serve as useful probes for their respective activities without concern for the off target effects of the parent compound.
Dibenzo[ b, f ]pyrazolo[1,5-d ][1,4]oxazepines: Facile construction of a rare heterocyclic system via tandem aromatic nucleophilic substitution-smiles rearrangement-denitrocyclization
Sapegin, Alexander V.,Kalinin, Stanislav A.,Smirnov, Alexey V.,Dorogov, Mikhail V.,Krasavin, Mikhail
experimental part, p. 2401 - 2407 (2012/09/07)
Condensation of 2-(1H-pyrazol-5-yl)phenols with 1-chloro-2-nitrobenzenes under basic conditions in N,N-dimethylformamide results in a tandem, atom-economical, aromatic nucleophilic substitution-Smiles rearrangement- denitrocyclization process to provide pyrazolo-fused dibenzo[b,f][1,4]oxazepines as a single regioisomer. Georg Thieme Verlag Stuttgart · New York.
BENZO-γ-PYRONES. PART XIII. REACTION OF CHROMONE AND ITS METHYL DERIVATIVES WITH THIOSEMICARBAZIDE
Maib, Piotr,Jerzmanowska, Zofia
, p. 111 - 122 (2007/10/02)
The reaction of chromone and its C-2 and C-3 substituted methyl derivatives was studied.New compounds in the systems of 2-pyrazoline (3, 14), 1,3-butanedione (9), pyrazole (4, 10, 11, 15) and chromone (7) were obtained.Methyl groups at C-2 and C-3 position desactivate the chromone system towards thiosemicarbazide.