Inhibitory effects of 5-benzylidene barbiturate derivatives on mushroom tyrosinase and their antibacterial activities

Yan, Qin; Cao, Rihui; Yi, Wei; Chen, Zhiyong; Wen, Huan; Ma, Lin; Song, Huacan

doi:10.1016/j.ejmech.2009.05.023

Cited by 82 publications

(41 citation statements)

References 18 publications

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“…The reason C-9 could inhibit the growth of microorganisms may be the same as that for caffeic acid. Recently, more and more tyrosinase inhibitors have been reported as antibacterial agents, such as 5-benzylidene barbiturate derivatives [39], leaf extracts [40] and even lactoferrin hydrolysates [41], yet without clear mechanisms. We offered a new method that combines the docking assay with a UV-scanning assay.…”

Section: Resultsmentioning

confidence: 99%

Anti-tyrosinase kinetics and antibacterial process of caffeic acid N-nonyl ester in Chinese Olive (Canarium album) postharvest

Jia

Zheng

Feng

et al. 2016

International Journal of Biological Macromolecules

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Enzymatic browning and bacterial putrefaction are mainly responsible for quality losses of Chinese Olive (Canarium album) postharvest and lead to very short shelf life on average. Screening anti-browning and anti-bacterial agents is important for preservation of Chinese Olive. Caffeic acid N-nonyl ester (C-9) and caffeic acid N- Heptyl ester (C-7) was synthesized as inhibitors of tyrosinase, which is a key enzyme in browning process. The compound of C-9 could inhibit the activity of tyrosinase strongly and its IC50 value was determined to be 37.5μM, while the compound of C-7 had no inhibitory ability. Kinetic analyses showed that compound of C-9 has been a reversible inhibitory mechanism below 50μM and been irreversible mechanisms above 50μM. For the reversible inhibitory mechanism, the values of inhibitory constants (KI and KIS) were determined to be 24.6 and 37.4μM, respectively. The results of Chinese Olive fruit postharvest showed that the compound of C-9 could effectively anti-browning and anti-bacterial putrefaction. In addition, this compound had strong antibacterial activities against Staphylococcus aureus, Escherichia coli, Bacillus subtilis and Salmonella. Therefore, C-9 could be a potential anti-browning and anti-bacterial reagent.

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Section: Resultsmentioning

confidence: 99%

Anti-tyrosinase kinetics and antibacterial process of caffeic acid N-nonyl ester in Chinese Olive (Canarium album) postharvest

Jia

Zheng

Feng

et al. 2016

International Journal of Biological Macromolecules

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“…For example, 5-benzylidene-barbiturates and thiobarbiturates (1c) show antibacterial activity [9]. Recently, we described the synthesis and evaluation of the antibacterial activity of model fluoroquinolonebarbiturates [10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of some new fluoroquinolone-barbiturate hybrid systems

Sweidan

El‐Abadelah

Haddad

et al. 2015

Zeitschrift Für Naturforschung B

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New hybrid molecules containing fluoroquinolone-barbiturate moieties were synthesized via simple routes, followed by characterization using various spectroscopic approaches. The THF solvent molecule was incorporated into compounds 2 and 3 through its oxygen atom based on its nucleophilicity. Facile displacement of the chloride ion in 4-oxoquinoline-3-carbonyl chloride by the nucleophilic methylene carbon of 1,3-dialkylbarbiturate/thiobarbiturate afforded the respective hybrids 5 and 6.

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“…5-Benzylidine barbiturate derivatives [7] inhibited the growth of mushroom tyrosinase and Gram-positive bacteria Staphylococcus aureus. Pyrimidine bases [8] exerted pronounced antiproliferative activity against the HeLa and MiaPaCa-2 cell lines.…”

Section: Introductionmentioning

confidence: 99%

Microwave assisted synthesis of dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-4-ones; synthesis, in vitro antimicrobial and anticancer activities of novel coumarin substituted dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-4-ones

Puttaraju

Shivashankar

Chandra

et al. 2013

European Journal of Medicinal Chemistry

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Microwave assisted synthesis of dihydrobenzo [4,5]imidazo [1,2-a] pyrimidin-4-ones; synthesis, in vitro antimicrobial and anticancer activities of novel coumarin substituted dihydrobenzo [4,5] In general, all the compounds possessed better antifungal properties than antibacterial properties. The coumarin substituted dihydrobenzo [4,5]imidazo[1,2-a]pyrimidin-4-one (4g) (R ¼ i-Pr, R 1 ¼ 6-Cl) was found to be the most potent cytotoxic compound (88%) against Dalton's Ascitic Lymphoma cell line at the concentration of 100 mg/mL.

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Inhibitory effects of 5-benzylidene barbiturate derivatives on mushroom tyrosinase and their antibacterial activities

Cited by 82 publications

References 18 publications

Anti-tyrosinase kinetics and antibacterial process of caffeic acid N-nonyl ester in Chinese Olive (Canarium album) postharvest

Anti-tyrosinase kinetics and antibacterial process of caffeic acid N-nonyl ester in Chinese Olive (Canarium album) postharvest

Synthesis and characterization of some new fluoroquinolone-barbiturate hybrid systems

Microwave assisted synthesis of dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-4-ones; synthesis, in vitro antimicrobial and anticancer activities of novel coumarin substituted dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-4-ones

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