A new strategy for the synthesis of biflavonoids via arylboronic acids.

Müller, D.; Fleury, Jean‐Pierre

doi:10.1016/s0040-4039(00)79688-2

Cited by 44 publications

(22 citation statements)

References 6 publications

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“…Pure samples of flavonoids 4,8,12,15,18,21,26 and the corresponding halogenated derivatives 5, 6,9,10,11,13,14,16,17,19,20,22,23,24,25,27,28 and 29 were screened in vitro at three different concentrations 0.5, 2.0 and 8.0 Â 10 À4 M 13,14,25 for their growth inhibitory activity against Trichoderma koningii, Fusarium oxysporum and Cladosporium cladosporioides, common saprotrophic soil and seed fungi, potential pathogens for humans. [26][27][28] All experimental results, expressed as linear mycelial growth inhibition (%), are reported in Table 2 and grouped in the MDS plot depicted in Fig.…”

Section: Evaluation Of the Antifungal Activitymentioning

confidence: 99%

Ecofriendly synthesis of halogenated flavonoids and evaluation of their antifungal activity

et al. 2015

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Brominated and chlorinated flavonoids belonging to different classes (flavanones, flavones and catechins) were prepared from the corresponding flavonoids by a simple and ecofriendly procedure based on the use of sodium halides, aqueous hydrogen peroxide and acetic acid. Pure samples of substrates and products were tested against Trichoderma koningii, Fusarium oxysporum and Cladosporium cladosporioides, common saprotrophic soil and seed fungi, potential pathogens for humans and their activity was expressed as linear mycelial growth inhibition (%). Among them, 8-chloro-5,7,3 0 ,4 0tetramethoxyepicatechin 29, a novel catechin derivative, exhibited a remarkable effect against all tested fungi also at low concentrations.

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Section: Evaluation Of the Antifungal Activitymentioning

confidence: 99%

Ecofriendly synthesis of halogenated flavonoids and evaluation of their antifungal activity

et al. 2015

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“…Another problem with this approach is the catalytic coupling of boronic acids 76 and 77 with 3'-iodoflavones 78 and 79 in which competitive protodeboronation of the boronic acid moiety occurs resulting in lower yields. However, the yield of the coupled products, biflavones 7e -7j ( Table 2) could be improved to nearly 90% through use of excess boronic acid derivatives [100] (Scheme 12). Alternatively, instead of direct coupling of the two flavone rings, the second flavone ring could be built after the Suzuki coupling of a benzeneboronic acid, as exemplified in the synthesis of 7d ( Table 2 and Scheme 13) [117].…”

Section: 3mentioning

confidence: 99%

“…Thus, boronic acid 80 was coupled with iodoflavone 78, followed by Lewis-acid catalyzed acylation of 81 with pmethoxycinnamic acid. In the course of acylation, regioselective demethylation of the diorthosubstituted MeO group occurred to give chalcone 82, from which the second flavone ring of [I-3',II-8]-biflavone 7d was built through a standard oxidative cyclization reaction [100] (Scheme 13).…”

Section: 3mentioning

confidence: 99%

Synthesis of Biologically Relevant Biflavanoids – A Review

Rahman

Riaz

Desai

2007

Chemistry & Biodiversity

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Recent investigations show that naturally occurring biflavanoids possess anti-inflammatory, anticancer, antiviral, antimicrobial, vasorelaxant, and anticlotting activities. These activities have been discovered from the small number of biflavanoid structures that have been investigated, although the natural biflavanoid library is likely to be large. Structurally, biflavanoids are polyphenolic molecules comprised of two identical or non-identical flavanoid units conjoined in a symmetrical or unsymmetrical manner through an alkyl or an alkoxy-based linker of varying length. These possibilities introduce significant structural variation in biflavanoids, which is further amplified by the positions of functional groups--hydroxy, methoxy, keto, or double bond--and stereogenic centers on the flavanoid scaffold. In combination, the class of biflavanoids represents a library of structurally diverse molecules, which remains to be fully exploited. Since the time of their discovery, several chemical approaches utilizing coupling and rearrangement strategies have been developed to synthesize biflavanoids. This review compiles these synthetic approaches into nine different methods including Ullmann coupling of halogenated flavones, biphenyl-based construction of biflavanoids, metal-catalyzed cross-coupling of flavones, Wessely-Moser rearrangements, oxidative coupling of flavones, Ullmann condensation with nucleophiles, nucleophilic substitutions for alkoxy biflavanoids, and dehydrogenation-based or hydrogenation-based synthesis. Newer, more robust synthetic approaches are necessary to realize the full potential of the structurally diverse class of biflavanoids.

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“…Terdapat banyak reaksi penggabungan silang untuk membentuk ikatan C−C dengan katalis metal, tetapi dalam sintesis biflavonoid hanya mencakup penggabungan Stille dan Suzuki, keduanya memanfaatkan palladium untuk menggabungkan gugus aril. Stille mensintesis biflavonoid melalui penggabungan silang antara flavon triflate dengan distannan (Echavarren dan Stille, 1987) (Gambar 2c1), sedangkan Suzuki dengan asam arilboronat (Muller, 1991) (Gambar 2c2). Metode Suzuki dapat digunakan untuk menjelaskan sintesis robustaflavon dan robustaflavon heksametil eter (Zembower dan Zhang, 1998), serta hinokiflavon (Flavin dkk., 2001).…”

Section: Sintesis Biflavonoidunclassified

Biflavonoid compounds of Selaginella Pal. Beauv. and its benefit

Setyawan¹

2008

Biodiversitas

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In the present day, medicinal plants increasingly play important role in human health, while about 60-75% of world population depending on plants and their extracts for medication. Selaginella Pal. Beauv. (Selaginellaceae Reichb.) is a potent medicinal plant source. This plant contains biflavonoid compounds, a dimeric form of flavonoids. Flavonoids are secondary metabolite that is most used in medical purposes. They are often occurred in daily consumed vegetables and fruits. Chemical constituents of flavonoids are very diverse, because they are generated in many biosynthetic methods. There are many biflavonoid compounds of Selaginella, i.e. amentoflavone, 2',8''-biapigenin, ginkgetin, heveaflavone, hinokiflavone, isocryptomerine, kayaflavone, podocarpusflavone A, robustaflavone, sumaflavone, and taiwaniaflavone. For the plants, these biflavonoid are used to response environmental condition such as defense against pests, diseases, herbivory, and competitions; while for the people, these compounds are used as antioxidant, anti-inflammatory, anti cancer, antimicrobial (antivirus, antibacterial, anti fungal, antiprotozoan), neuroprotective, vasorelaxant, anti UV-irradiation, antispasmodic, anti allergic, antihaemorrhagic, antinociceptive, etc. The antioxidant purpose of biflavonoid is the most important activities of this secondary metabolite. It is related to the anti cancer and anti-inflammatory functions. The antioxidant of biflavonoid is more powerful than β-carotene, vitamin C and E. In the future, Selaginella research exhaustively needs to be conducted on morphological and molecular characteristics. It deeply needs to explore on biflavonoid and other natural products constituents, and it also needs to search on their bioactivities.

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A new strategy for the synthesis of biflavonoids via arylboronic acids.

Cited by 44 publications

References 6 publications

Ecofriendly synthesis of halogenated flavonoids and evaluation of their antifungal activity

Ecofriendly synthesis of halogenated flavonoids and evaluation of their antifungal activity

Synthesis of Biologically Relevant Biflavanoids – A Review

Biflavonoid compounds of Selaginella Pal. Beauv. and its benefit

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