7145-48-4Relevant 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.
Studies with functionally substituted enamines: Synthesis of 2-aroyl-3-dimethylamino-2-propenenitrile and their reactivity toward nitrogen nucleophiles
Al-Qalaf, Fawzia,Abdelkhalik, Mervat Mohammed,Al-Enezi, Amal,Al-Ajmi, Johara Rashed
, p. 145 - 156 (2008/09/20)
A facile and efficient synthesis of 2-substituted 3-dimethylamino-2-propenenitrile 4a-c is described. Reaction of 4a-c with hydrazine hydrate afforded 3-substituted-1H-4-pyrazole carbonitrile 9a-c. Compounds 4a-c reacted with 5-methyl-1H-pyrazol-3-amine to give 7-substituted pyrazolo[1,5-a]pyrimidine-6-carbonitrile 12a-c and 2-substituted 5-aminopyrazolo[1,5-a]pyrimidine 16a,b, and with 1H-benzo[d]imidazol-2-amine to give 3-substituted 2-aminobenzo[4,5]imidazo[1,2-a]pyrimidine 19a,b and 4-substituted benzo[4,5]imidazo[1,2-a]pyrimidine 3-carbonitrile 21c. The structures of compounds obtained were deduced based on 1HNMR, HMBC-15N and NOE difference experiments.
Pyrolytic methods in organic synthesis: Novel routes for the synthesis of 3-oxoalkanenitriles, 2-acyl anilines, and 2-aroyl anilines
Al-Awadi, Nouria A.,Abdelkhalik, Mervat M.,Abdelhamid, Ismail A.,Elnagdi, Mohamed H.
, p. 2979 - 2982 (2008/03/12)
3-Oxoalkanenitriles 1a-d were obtained in high yield by treating enaminones 6a-d with hydroxylamine hydrochloride and stirring the resulting oxime with diethyl oxalate. The formed 3-oxoalkanenitriles 1a,b readily undergo self-condensation to yield 2-aroylanilines 3a,b on heating in pyridine for eight hours or by irradiation in microwave for 1.5 minutes. In contrast, 1c-e were recovered unreacted under similar conditions. Pyrolysis of 3-aminocrotononitrile 14 produced a mixture of the aminopyridine 16, 19, and aminobenzene 22. Heating 14 in aqueous media has resulted in formation of the pyridine 20, while heating the same compound in acetic acid has afforded pyridone 20 and acetyl pyridine 24. Georg Thieme Verlag Stuttgart.
Studies with 2-Arylhydrazono-3-oxopropanals: A novel route to 4-aroyl-2-aryl-1,2,3-triazoles, 3-substituted 4-arylazopyrazoles, 2-substituted glyoxalonitrile and 3-oxoalkanonitriles
Abdel-Khalik, Mervat Mohammed,Agamy, Samia Michel,Elnagdi, Mohammed Hilmy
, p. 1211 - 1215 (2007/10/03)
2-Arylhydrazono-3-oxopropanals 1 react with hydroxylamine hydrochloride to yield the corresponding oximes 3 that are cyclized into isoxazoles 9 on reflux in acetic anhydride and are converted into 2-arylhydrazono-3-oxonitriles (4) on treatment with pyridine. The reaction of 1 with hydrazines afforded dihydrazones 10 which were converted to arylazopyrazoles 11 when treated with pyridine, whereas treatment with an acidic reagent resulted in the formation of 3-aroyl-2-phenyl-1,2,3-triazoles 12.
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.
