34810-67-8Relevant 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.
Reusable manganese compounds containing pyrazole-based ligands for olefin epoxidation reactions
Manrique, Ester,Poater, Albert,Fontrodona, Xavier,Solà, Miquel,Rodríguez, Montserrat,Romero, Isabel
, p. 17529 - 17543 (2015/10/19)
We describe the synthesis of new manganese(ii) and manganese(iii) complexes containing the bidentate ligands 2-(3-pyrazolyl)pyridine, pypz-H, and 3(5)-(2-hydroxyphenyl)pyrazole, HOphpz-H, with formula [MnX2(pypz-H)2] (X = Cl-, 1, CF3SO3-, 2, OAc-, 3 or NO3- (4)), [MnCl2(pypz-H)(H2O)2], 5, or [MnCl(Ophpz-H)2], 6. All the complexes have been characterized through analytical, spectroscopic and electrochemical techniques. Single X-ray structure analysis revealed a six-coordinated Mn(ii) ion in complexes 1-5, and a five-coordinated Mn(iii) ion in complex 6. Compound 5 is the first co-crystal of Mn(ii) containing Cl and H2O ligands together with bidentate nitrogen ligands. The catalytic activity of complexes 1-6 has been tested with regard to the epoxidation of styrene and, in the case of 1, 5 and 6, other alkenes have been epoxidized using peracetic acid as oxidant in different media, among which glycerol, a green solvent never used in epoxidation reactions using peracetic acid as oxidant. The catalysts show moderate to high conversions and selectivities towards the corresponding epoxides. For complexes 1, 5 and 6, a certain degree of cis → trans isomerization is observed in the case of cis-β-methylstyrene. These observations have been explained through computational calculations. The reutilization of catalysts 1 and 6 for the epoxidation of alkenes has been evaluated in [bmim]:acetonitrile mixture (bmim = 1-butyl-3-methylimidazolium), allowing the effective recyclability of the catalytic system and keeping high conversion and selectivity values up to 12 successive runs, in all cases.
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.
