Synthesis, structural characterisation and biological evaluation of fluorinated analogues of resveratrol

Moran, Brian W.; Anderson, Frankie P.; Devery, Aoife; Cloonan, Suzanne M.; Butler, William E.; Varughese, Sunil; Draper, Sylvia M.; Kenny, Peter T.M.

doi:10.1016/j.bmc.2009.05.007

Cited by 41 publications

(27 citation statements)

References 24 publications

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“…They investigated the biological activities of these compounds in different cell lines and identified a number of active analogues. Aromatic hydroxylation of two hydroxylated methoxystilbenes led to two new compounds, which were evaluated as anti-angiogenic agents (44).…”

Section: Other Resveratrol Analoguesmentioning

confidence: 99%

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Resveratrol and Resveratrol Analogues—Structure—Activity Relationship

et al. 2010

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Resveratrol (3,4',5-trihydroxy-trans-stilbene) is a compound found in wine and is held responsible for a number of beneficial effects of red wine. Besides the prevention of heart disease and significant anti-inflammatory effects, resveratrol might inhibit tumor cell growth and even play a role in the aging process. We here describe the structure-activity relationship of resveratrol and analogues of resveratrol regarding the free radical scavenging and antitumor effects of this exciting natural compound. In addition, we have synthesized a number of analogues of resveratrol with the aim to further improve the beneficial effects of resveratrol. Our studies were based on the analysis of structural properties, which were responsible for the most important effects of this compound. Striking in vivo effects can be observed with hexahydroxystilbene (M8), the most effective synthetic analogue of resveratrol. We could show that M8 inhibits tumor as well as metastasis growth of human melanoma in two different animal models, alone and in combination with dacarbacine.

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Section: Other Resveratrol Analoguesmentioning

confidence: 99%

“…Fluorinated derivatives of resveratrol with hydroxyl groups replaced by amino groups were synthesized by Moran et al (44). They investigated the biological activities of these compounds in different cell lines and identified a number of active analogues.…”

Section: Other Resveratrol Analoguesmentioning

confidence: 99%

Resveratrol and Resveratrol Analogues—Structure—Activity Relationship

et al. 2010

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“…[5] In this laboratory, fluorinated amino analogs of the natural phytoalexin resveratrol were prepared generate stilbenes with improved biological activity. [6] Reduction of the nitro group of (E)-3,5-difluoro-4 0 -nitrostilbene (1a) via a palladium-catalyzed siloxane (PMHS) aqueous potassium fluoride procedure, [7] yielded the amino compound 1b and an unexpected by-product. The by-product was identified by spectroscopic analysis as 4-f4 0 -(3,5-difluorophenylethyl)phenylaminogbutan-1-ol 1c (Fig.…”

Section: Introductionmentioning

confidence: 99%

Formation of 4-N-Arylamino-1-butanol Derivatives from Aromatic Nitro Compounds via a Novel Palladium-Catalyzed Tetrahydrofuran Ring-Opening Reaction

Moran

Kenny

2012

Synthetic Communications

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“…Moran et al, in 2009 have synthesized fluorinated stilbene analogues and evaluated against variety of cell lines, primarily the nonsmall lung carcinoma cell lines. They explained that (E)-3,5-difluoro-4 0 -acetoxy stilbene showed greater potency than that of 3,5,4 0 -trihydroxy-trans-stilbene.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of some stilbene-based analogues

et al. 2010

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The phytoalexin 3,5,4 0 -trihydroxy-trans-stilbene (resveratrol) has attracted considerable attention from biologists and chemists due to its diverse biological properties. Owing to the biological importance of this compound, we have synthesized new stilbene-based analogues by using substituted benzyl chlorides and substituted aldehydes in a two-step reaction and evaluated their in vitro antioxidant, antibacterial and antifungal potential. Most of the compounds displayed moderate to significant radical scavenging activity. (E)-1-(3,4-difluorophenyl)-2-(4-fluorophenyl)ethene (4c) showed nearer equipotent antibacterial activity against Staphylococcus aureus. (E)-1,2-bis (4-fluorophenyl)ethene (4a), (E)-1-(3-fluorophenyl)-2-(4-fluorophenyl)ethene (4b), (E)-1-(2,4-dichlorophenyl)-2-(3, 4-dichlorophenyl)ethene (4f), (E)-1-(2,4-dichlorophenyl)-2-(3-chlorophenyl)ethene (4g), (E)-1-(2,4-dichlorophenyl)-2-(4-fluorophenyl)ethene (4j) (E)-1-(4-fluorophenyl)-2-(3-chlorophenyl)ethene (4l) and (E)-1-(4-chlorophenyl)-2-(4-fluorophenyl)ethene (4n) inhibited the growth of Penicillium chrysogenum.

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Synthesis, structural characterisation and biological evaluation of fluorinated analogues of resveratrol

Cited by 41 publications

References 24 publications

Resveratrol and Resveratrol Analogues—Structure—Activity Relationship

Resveratrol and Resveratrol Analogues—Structure—Activity Relationship

Formation of 4-N-Arylamino-1-butanol Derivatives from Aromatic Nitro Compounds via a Novel Palladium-Catalyzed Tetrahydrofuran Ring-Opening Reaction

Synthesis and biological evaluation of some stilbene-based analogues

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