(2-Arylhydrazonomethyl)-substituted xanthones as antimycotics: synthesis and fungistatic activity against Candida species

Moreau, Stéphane; Varache‐Lembege, Martine; Larrouture, Stéphane; Fall, Dioumacor; Neveu, Arlette; Deffieux, Gérard; Vercauteren, Joseph; Nuhrich, A.

doi:10.1016/s0223-5234(01)01332-0

Cited by 26 publications

(15 citation statements)

References 27 publications

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“…In the Grover, Shah, and Shah (GSS) reaction (see Scheme 1), better results were obtained using a mixture of phosphorus pentoxidemethanesulfonic acid (Eaton's reagent) instead of phosphorus oxychloride-zinc chloride as catalyst [46,54]. The former acylation catalyst was found to be an excellent condensing agent between phloroglucinol (5) and 3-methylsalicylic acid (6), providing high yields (90-95%) of the xanthone (7) and no detectable amounts of the possible benzophenone (8) (Scheme 3).…”

Section: Modifications To the Classical Methodsmentioning

confidence: 99%

“…A novel approach to the synthesis of substituted xanthones was developed using the [4+2] cycloaddition reactions of enamines with aromatically substituted vinylchromones (Scheme 15) [98]. With this method, 1-methyl-and 1-ethyl-xanthones (55) were obtained in a onepot synthesis from the reaction of pyrrolidine enamines (54) obtained in situ from the corresponding alkyl ketones with vinylchromones, when taken as solvent a catalytic amount of pyrrolidine (Scheme 15). 1-Methylidene-and 1-methylidene-2-methyl-substituted tetrahydroxanthones (56) were also obtained as byproducts (Scheme 15) and were proposed as intermediates in the reaction, since they underwent facile conversion to 1-methyl-and 1,2-dimethylxanthones.…”

Section: New Approaches To the Synthesis Of The Xanthonic Tricyclic Smentioning

confidence: 99%

“…However, protection of the chelated phenol groups proved to be essential to carry out the palladium catalyzed carbonylation. The substituents most frequently inserted in the aromatic rings after the xanthone nucleus formation are acetyl [141], formyl [121], halogens [54,115,[142][143][144][145], and nitro groups [113,138]. Nevertheless, this strategy is limited because the pattern of substitution thus obtained often follows the electrophilic aromatic substitution rules and/or also depends on the presence of bulky groups.…”

Section: Strategies To Introduce Simple Substituents Into the Xanthonmentioning

confidence: 99%

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Synthesis of Xanthones: An Overview

Sousa¹,

Pinto

2005

CMC

125

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Among the known synthetic routes to obtain xanthones, the Grover, Shah, and Shah reaction, the cyclodehydration of 2, 2'-dihydroxybenzophenones and electrophilic cycloacylation of 2-aryloxybenzoic acids are the most popular methods. Due to important biological applications of xanthones, some synthetic strategies leading to more complex derivatives have been widely explored in the past years. Thus, the purpose of this review is to report some recent improvements of the classical synthetic methods as well as of some non-classical methods to obtain simple oxygenated xanthones. The strategies for introduction of substituents into the xanthonic nucleus are also summarized. Furthermore, different approaches used to synthesize complex structures, with an emphasis on the total synthesis of bioactive natural products, accomplished in the last twenty years, are also discussed. Besides the synthesis of xanthones, the reactivity of the xanthonic nucleus and its role as a key intermediate for the synthesis of other important classes of compounds are also highlighted.

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Section: Modifications To the Classical Methodsmentioning

confidence: 99%

Section: New Approaches To the Synthesis Of The Xanthonic Tricyclic Smentioning

confidence: 99%

Section: Strategies To Introduce Simple Substituents Into the Xanthonmentioning

confidence: 99%

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Synthesis of Xanthones: An Overview

Sousa¹,

Pinto

2005

CMC

125

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“…Hydroxylated xanthones ( 32b-i , 32k-q ) were produced through a cyclization reaction between phloroglucinol ( 30 ) and appropriate substituted salicylic acids ( 31b-j , 31l-q ), in the presence of Eaton's reagent (phosphorus pentoxide solution in methanesulfonic acid) as a catalytic condensation agent [7]. A slight excess of phloroglucinol was used to complete the desired reaction and avoid the formation of side products (hydroxychromeno[3,2- b ]xanthenediones).…”

Section: Chemistrymentioning

confidence: 99%

Anti-AIDS agents 85. Design, synthesis, and evaluation of 1R,2R-dicamphanoyl-3,3-dimethyldihydropyrano-[2,3-c]xanthen-7(1H)-one (DCX) derivatives as novel anti-HIV agents

Zhou

Shi

Chen

et al. 2012

European Journal of Medicinal Chemistry

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In this study, 1R,2R-dicamphanoyl-3,3-dimethydihydropyrano[2,3-c]xanthen-7(1H)-one (DCX) derivatives were designed and synthesized as novel anti-HIV agents against both wild-type and nonnucleoside reverse transcriptase (RT) inhibitor-resistant HIV-1 (RTMDR-1) strains. Twenty-four DCX analogs (6-29) were synthesized and evaluated against the non-drug-resistant HIV-1 NL4-3 strain, and selected analogs were also screened for their ability to inhibit the RTMDR-1 strain. Compared with the control 2-ethyl-3′,4′-di-O-(-)-camphanoyl-2′,2′-dimethyldihydropyrano[2,3-f]chromone (2-EDCP, 2), one of the best anti-HIV coumarin derivatives in our prior study, three DCX compounds (7, 12, and 22) showed better activity against both HIV strains with an EC50 range of 0.062 – 0.081 μM, and five additional compounds (8, 11, 16, 18, and 21) exhibited comparable anti-HIV potency. Six DCX analogs (7, 11-12, 18, and 21-22) also showed enhanced selectivity index (SI) values in comparison to the control. Structure-activity relationship (SAR) information suggested that the extended conjugated system of the pyranoxanthone skeleton facilitates the interaction of the small DCX molecule within the viral binding pocket, consequently leading to enhanced anti-HIV activity and selectivity. Compared to DCP compounds, DCX analogs are a more promising new class of anti-HIV agents.

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“…Os fragmentogramas dos metabólitos presentes na subfração AcOEt-FRU-13 (Figura 73 e Figura 74) mostrou padrão de fragmentação semelhante aos encontrados para algumas xantonas, isoladas em trabalhos anteriores de diversas espécies do gênero Garcinia (PANTHONG, et al, 2006;HARRISON, et al, 2005;IINUMA, et al, 1996;ZHOU, et al, 2008;MOREAU, et al, 2002;SCHIEBER;BERARDINI;CARLE, 2003 esqueleto xantônico triidroxilado e dimetoxilado, como relatado para xantonas isoladas em trabalhos anteriores (BASHIR et al, 1992;FUJITA et al, 1992;IKEYA et al, 1991 (Figuras 83 e 84). Nota-se por fim, que a substância 6 é muito semelhante a 11, diferindo apenas no padrão de substituição do anel B (livre de hidroxila na posição C-3''') podendo ser identificada com GB1a, um biflavonóide isolado dos frutos de G.…”

Section: Identificação Por Clae-uv-dad-em Dos Constituintes De Garcinunclassified

Estudo químico e atividade biológica de Garcinia xanthochymus (Clusiaceae)

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(2-Arylhydrazonomethyl)-substituted xanthones as antimycotics: synthesis and fungistatic activity against Candida species

Cited by 26 publications

References 27 publications

Synthesis of Xanthones: An Overview

Synthesis of Xanthones: An Overview

Anti-AIDS agents 85. Design, synthesis, and evaluation of 1R,2R-dicamphanoyl-3,3-dimethyldihydropyrano-[2,3-c]xanthen-7(1H)-one (DCX) derivatives as novel anti-HIV agents

Estudo químico e atividade biológica de Garcinia xanthochymus (Clusiaceae)

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