Synthesis and antimicrobial activity of 4-hydroxy-1-methyl/phenyl-3- (substituted anilinoacetyl) quinolin-2(1H)-one

Girish, Bolakatti; Manjunatha, S. Katagi; Mamledesai, S. N.; M.L.Sujatha,; Dabadi, Prakash; Narayana, M.S. Sandeep Veda

doi:10.5530/rjps.2012.1.8

Cited by 5 publications

(2 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the search for a new scaffold for antimicrobial drugs, 4-hydroxy-2-quinolone, a class of heterocyclic compound, has shown great potential, as various analogs of 4-hydroxy-2-quinolone including Roquinimex (Linomide), a synthetic immunomodulator [ 3 ], have been reported to possess a wide range of biological activities such as antibacterial [ 4 ], antifungal [ 5 ], anticancer [ 6 ], antioxidant [ 7 ], and so on. Over the past few decades, several attempts have been made to investigate the structure–activity relationship of the antimicrobial activity of this scaffold; for instance, the derivatives of 4-hydroxy-2-quinolone bearing chalcones [ 8 ], pyrimidines [ 9 ], pyrazoles [ 10 ], and thiadiazole [ 11 ] ( Figure 1 a).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Novel 4-Hydroxy-2-quinolone Analogs

Khamkhenshorngphanuch

Kulkraisri

Janjamratsaeng

et al. 2020

Molecules

View full text Add to dashboard Cite

Alkyl quinolone has been proven to be a privileged scaffold in the antimicrobial drug discovery pipeline. In this study, a series of new 4-hydroxy-2-quinolinone analogs containing a long alkyl side chain at C-3 and a broad range of substituents on the C-6 and C-7 positions were synthesized. The antibacterial and antifungal activities of these analogs against Staphylococcus aureus, Escherichia coli, and Aspergillus flavus were investigated. The structure-activity relationship study revealed that the length of the alkyl chain, as well as the type of substituent, has a dramatic impact on the antimicrobial activities. Particularly, the brominated analogs 3j with a nonyl side chain exhibited exceptional antifungal activities against A. flavus (half maximal inhibitory concentration (IC50) = 1.05 µg/mL), which surpassed that of the amphotericin B used as a positive control. The antibacterial activity against S. aureus, although not as potent, showed a similar trend to the antifungal activity. The data suggest that the 4-hydroxy-2-quinolone is a promising framework for the further development of new antimicrobial agents, especially for antifungal treatment.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Novel 4-Hydroxy-2-quinolone Analogs

Khamkhenshorngphanuch

Kulkraisri

Janjamratsaeng

et al. 2020

Molecules

View full text Add to dashboard Cite

show abstract

“…Among the various heterocyclic compounds, quinolinone derivatives including 2-and 4-quinolinones occur in many natural products such as coal tar, oil, herbs, and dyes. [1][2] 2-Quinolinones have long been targeted in synthetic research due to their sound biological activities and pharmacological properties, which include antiparasitic activity, 3,4 antimicrobial potency, 5,6 antioxidant effect, antiinflammatory activity, 7 anti-convulsion, 8 anti-hepatitis C and B viruses activity, 9,10 anticancer and antitumor activity, 11,12 androgen receptor modulation, 13 CB2 receptor inverse antagonist, potent CDK-5 inhibition, 14 steroid-5a reductase-types inhibition, 15 and potential Rho-kinase inhibition. 16 The great importance of this category of heterocycles oriented our attention to the synthesis of a series of new heterocyclic derivatives combining both known biologically active heterocycles and quinoline in one molecular-frame.…”

mentioning

confidence: 99%

Substituted Quinolinones. Part 27. Regioselective Heterocyclization of Some Diazolo- and/or Triazepino[b or c]quinoline Derivatives

Abass

Hassanin

Allimony

et al. 2015

Proceedings of the 19th International Electronic Conference on Synthetic Organic Chemistry

View full text Add to dashboard Cite

Reactivity of 3-acetyl-4-methylthioquinolin-2(1H)-one (1) towards 1,2-and/or 1,4-diazanucleophiles has been studied under different reaction conditions. Condensation of key compound 1 with hydrazine, phenylhydrazine, hydroxylamine hydrochloride, semicarbazide and thiosemicarbazide was carried out in different media. It was found that the nature of products is extremely dependent on both reactivity of the reagent and the ambient conditions. Accordingly, the reaction regioselectivety led to different [1,2]diazolo and or [1,2,4]triazepino[b or c]quinoline derivatives in addition to open chain condensates which were transformed to either annellated heterocyclo[b or c] quinolines, in good yields. The structure of new products was established on basis of their analytical and spectral data.

show abstract