Synthesis and structure–activity relationships of thioflavone derivatives as specific inhibitors of the ERK-MAP kinase signaling pathway

Kataoka, Tadashi; Watanabe, Shinichi; Mori, Etsuro; Kadomoto, Ryoji; Tanimura, Susumu; Kohno, Michiaki

doi:10.1016/j.bmc.2004.02.002

Cited by 49 publications

(15 citation statements)

References 40 publications

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“…Sulfur atoms in the flavone structure might block enzymatic activity in microorganisms and in doing so prevent bacterial division and growth (Lee, ). Kataoka et al () reported that the isosteric replacement of the oxygen atom by a sulfur atom causes modified chemical and biological activity. Also, the results of a study by Ehsan et al () demonstrated that thio‐analogues of flavones have stronger antibacterial activities compared to flavones.…”

Section: Resultsmentioning

confidence: 99%

Inhibitory effect of novel thioflavone derivatives against foodborne and spoilage microbes on fresh fruit

Jang¹,

Kim

2017

Journal of Food Safety

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In this study, the antimicrobial activities of four thioflavones against foodborne and food spoilage bacteria (Three Gram‐positive and Five Gram‐negative bacteria) and one fungus were assessed. Antimicrobial effects of the thioflavones were evaluated using broth micro‐dilution and agar dilution assays. We generated survival curves based on the kinetics of bacterial inactivation after 24 hr of thioflavone exposure. The minimum inhibitory concentrations (MIC) for the microorganisms tested were 8–120 μg/mL. The minimum bactericidal concentrations (MBC) were 60–120 μg/mL. We evaluated three novel thioflavone derivatives and found that they exhibited strong antimicrobial activities against most of the microorganisms tested. In an in vivo antifungal study, thioflavone treatments reduced fungal decay, and 4'‐chloro‐thioflavone at a concentration of 120 μg/mL showed complete control of Rhizopus sp. in wound‐inoculated fruit. Practical applications There is an urgent need for the development of new classes of antimicrobial compounds and the new thioflavone derivatives represent such a development. Thioflavones are sulfur‐containing flavones that inhibit the growth of foodborne pathogens and food spoilage microorganisms. Foodborne spoilage by bacteria or fungi cause postharvest decay and rapid deterioration, which affects the quality and shortens the shelf life of fruits and vegetables. We believe that these new thioflavone derivatives provide a viable alternative as a food preservative can extend shelf life of fruits and vegetables.

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Section: Resultsmentioning

confidence: 99%

Inhibitory effect of novel thioflavone derivatives against foodborne and spoilage microbes on fresh fruit

Jang¹,

Kim

2017

Journal of Food Safety

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“…Deprotection and subsequent cyclization were performed as a one-pot reaction in the presence of formic acid. 10,11 The reaction conditions were found to be inappropriate for synthesis of 5methoxythioflavanones, because the methoxy group was partially cleaved in the presence of formic acid. 12 However, 5-methoxy derivatives could be prepared if silver nitrate in ethanol was used to deprotect the 4-methoxybenzyl sulfides.…”

Section: Scheme 1 General Methods For the Synthesis Of Thioflavanonesmentioning

confidence: 99%

“…Flavonoids are a well-known source of inspiration in the search for new medicines. 1 Surprisingly, however, the biological activity of their sulfur analogues has been relatively little explored, [2][3][4][5][6][7][8] even though it has been found that replacement of the oxygen atom by sulfur does not deprive the compounds of activities, 3a,6,8 and sometimes can even improve it.…”

mentioning

confidence: 99%

Synthesis of Thioflavanone and Flavanone Derivatives by Cyclization of Chalcones

Konieczny¹,

Konieczny²

2009

Synthesis

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“…Sulfur-containing heterocycles, such as thiochromanone, thioflavanone, thiochromone, thioflavone, and their derivatives ( Scheme 1 ) have been reported to display rich biological activities. For example, thioflavonoids, which are the sulfur analogues of flavonoids [ 12 , 13 , 14 , 15 , 16 , 17 , 18 ], display many biological activities, such as antimicrobial, antioxidant, inhibiting nitric oxide production, and antifungal et al [ 3 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ] Thiochroman-4-ones have been reported to display antifungal activities. Some thiochroman-4-one derivatives have been studied and shown to display the cytotoxic effect on tumor cells in vitro [ 28 ].…”

Section: Introductionmentioning

confidence: 99%

Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications

et al. 2018

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Lithium dialkylcuprates undergo conjugate addition to thiochromones to afford 2-alkylthiochroman-4-ones in good yields. This approach provide an efficient and general synthetic approach to privileged sulfur-containing structural motifs and valuable precursors for many pharmaceuticals, starting from common substrates-thiochromones. Good yields of 2-alkyl-substituted thiochroman-4-ones are attained with lithium dialkylcuprates, lithium alkylcyanocuprates or substoichiometric amount of copper salts. The use of commercially available inexpensive alkyllithium reagents will expedite the synthesis of a large library of 2-alkyl substituted thiochroman-4-ones for additional synthetic applications.

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Synthesis and structure–activity relationships of thioflavone derivatives as specific inhibitors of the ERK-MAP kinase signaling pathway

Cited by 49 publications

References 40 publications

Inhibitory effect of novel thioflavone derivatives against foodborne and spoilage microbes on fresh fruit

Inhibitory effect of novel thioflavone derivatives against foodborne and spoilage microbes on fresh fruit

Synthesis of Thioflavanone and Flavanone Derivatives by Cyclization of Chalcones

Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications

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