133436-90-5Relevant articles and documents
Synthesis and antibacterial evaluation of novel 4-alkyl substituted phenyl β-aldehyde ketone derivatives
Liu, Jinbing,Cao, Rihui,Wu, Qifeng,Ma, Chunming,Wang, Zihou,Peng, Wenlie,Song, Huacan
experimental part, p. 1737 - 1744 (2009/05/30)
A series of novel 4-alkylphenyl β-aldehyde ketones and their derivatives were designed and synthesized on the basis of the chemical structures of Houttuynin and β-lactam antibiotics. Antibacterial activities of these compounds were investigated. The results demonstrated that most of the compounds tested had moderate antibacterial activities against Gram-positive pathogen Staphylococcus aureus (ATTC-25923) than Houttuynin, and Gram-positive bacteria were more susceptible to the compounds than Gram-negative bacteria. Compound 23 was found to be the most potent compound with MIC of 1.0 μg/mL against S. aureus. Particularly, compounds 16, 22 and 23 showed more active antibacterial activities against the clinically important pathogenic bacteria, methicillin-resistant S. aureus (MRSA) than Houttuynin and levofloxacin. The preliminary structure-activity relationship (SAR) analysis suggested that (1) the introduction of appropriate alkyl substituents into position 4 of phenyl ring enhanced antibacterial activities of these compounds, and isopropyl substituent might be more favorable; (2) the presence of ketone carbonyl moiety might play a vital role in determining significant antibacterial activities of these compounds.
SYNTHESIS OF PYRAZOLE, 1,3,4-THIADIAZOLE, AND 1,2,4-TRIAZOLE DERIVATIVES BY CONDENSATION OF 1,3-DIOXO COMPOUNDS WITH THIOSEMICARBAZIDE DERIVATIVES
Zelenin, K. N.,Solod, O. V.,Alekseev, V. V.,Pekhk, T. I.,Kuznetsova, O. B.,et al.
, p. 1051 - 1060 (2007/10/02)
The reaction of β-diketones with 2-unsubstituted thiosemicarbazides leads to the formation of the corresponding 1-thiocarbamoyl-5-hydroxy-2-pyrazolines, which readily undergo aromatization to give pyrazoles, while the reaction of benzoylacetaldehyde leads to the formation of the corresponding hydrazone.Acetylacetone 2-methyl- and 2,4-dimethylthiosemicarbazones are inclined to undergo tautomerization and, depending on the conditions, can exist in enehydrazine, hydrazone, 1,2,4-triazoline, and 1,3,4-thiadiazoline forms or mixtures of these forms.Upon heating these substances are converted to mixtures of the 1,3,5-trimethylpyrazole and the corresponding 1,2,4-triazoline-5-thione.The structures of the compounds were studied by means of IR and 1H, 13C, and 15N NMR spectroscopy and mass spectrometry.
