3617-16-1Relevant academic research and scientific papers
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.
Cation-Anion Combination Reactions. 20. Reactions of Nucleophiles with trans-3-Methoxy- and trans-3-(Methylthio)acrylophenones
Ritchie, Calvin D.,Kawasaki, Atsushi
, p. 4704 - 4708 (2007/10/02)
The reactions of a number of nucleophiles with trans-3-methoxyacrylophenone (MeOAcr) and with trans-3-(methylthio)acrylophenone (MeSAcr) in water and methanol have been studied.The reactions of amines produce enamines as the first observable products, and primary amines show simple kinetics: first-order with respect to amine and first-order with respect to the acrylophenone.Piperidine reactions show kinetics which are consistent with a change in the rate-determining step with a change in amine concentration.Methoxylamine reactions produce the monooximes, and semicarbazide reactions produce the monosemicarbazone with MeOAcr but the disemicarbazone with MeSAcr.The reactions of hydroxide ion produced the enolate of benzoylacetaldehyde, which, at the high base concentration used in the MeSAcr reaction, was further converted to acetophenone and formate ion.Methoxide and cyanide ion reactions given addition across the double bond.Rate constants for the reactions of MeOAcr are 20-1000 times greater than those for corresponding reactions of MeSAcr.There is a very good correlation of the rate constants for reactions of nucleophiles with MeOAcr and those with 2,4-dinitrophenyl acetate in both water and methanol solution.
