New total synthesis of bikaverin

Bekaert, Alain; Andrieux, Jean; Plat, M.

doi:10.1016/s0040-4039(00)78863-0

Cited by 119 publications

(41 citation statements)

References 4 publications

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“…5 The other useful applications of this heterocycles are as dyes, 6 fluorescent materials for visualization of biomolecules, 7 and in laser technologies. 8 Many procedures have been developed for the synthesis of xanthenes and benzoxanthenes, which include trapping of benzynes by phenols, 9 cyclocondensation between 2-hydroxyaromatic aldehydes and 2-tetralone, 10 cyclodehydrations, 11 and intramolecular phenyl carbonyl reaction of aldehydes with 5,5-dimethylcyclohexane-1,3-dione 12 or β-naphthol. 13 Furthermore, the synthesis of benzoxanthenes and their related products include the reaction of β-naphthol with formamide, 14 carbon monoxide, 15 2-naphthol-1-methanol, 16 aldehydes and cyclic 1,3-dicarbonyl compounds.…”

Section: Introductionmentioning

confidence: 99%

Silica supported perchloric acid: an efficient catalyst for the synthesis of 14-aryl-14H-dibenzo[a,i]xanthene-8,13-diones

Wu¹,

Wu²,

Yang³

et al. 2010

J. Braz. Chem. Soc.

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Este trabalho descreve a obtenção de 14-aril-14H-dibenzo [a,i]xanteno-8,13-dionas, com excelentes rendimentos e em um curto tempo de reação, a partir da reação de condensação do β-naftol com aldeídos aromáticos e 2-hidroxinaftaleno-1,4-dionas na presença de sílica suportada em ácido perclórico em um meio livre de solvente. A reação é muito simples e o catalisador pode ser separado facilmente da mistura reacional e, ainda, ser reutilizado por muitas vezes em reações subseqüentes.The condensation of β-naphthol with aromatic aldehydes and 2-hydroxynaphthalene-1,4-dione in presence of silica supported perchloric acid under solvent-free media to afford the corresponding 14-aryl-14H-dibenzo[a,i]xanthene-8,13-diones in excellent yields and short reaction times is described. The reaction work-up is very simple and the catalyst can be easily separated from the reaction mixture and reused several times in subsequent reactions.

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Section: Introductionmentioning

confidence: 99%

Silica supported perchloric acid: an efficient catalyst for the synthesis of 14-aryl-14H-dibenzo[a,i]xanthene-8,13-diones

Wu¹,

Wu²,

Yang³

et al. 2010

J. Braz. Chem. Soc.

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“…Many synthetic strategies has been developed for synthesis of xanthenes and benzoxanthenes because of their pharmacological and biological activities such as cyclo-acylation of carbamates 11 , trapping of benzynes by phenol 12 , cyclocondensation between 2-hydroxy aromatic aldehydes and 2-tetralone 13 , cyclodehydrations 14 and cyclization of polycyclic aryltriflate esters 15 . Recently the synthesis of benzoxanthenes has been achieved by the condensation of aromatic aldehydes with 2-naphthol by cyclodehydration in the presence of various catalysts such as amberlyst-15 16 , sulfamic acid 17 , molecular iodine 18 , Al(HSO 4 .…”

Section: Introductionmentioning

confidence: 99%

Nano Nickel-Cobalt Ferrite Catalyzed One Pot Synthesis of 14-Aryl-14H-Dibenzo[A, J]Xanthenes and 12-Aryl-8, 9, 10, 12-Tetrahydrobenzo[A]Xanthene-11-One Derivatives

Korupolu¹,

Maripi²,

Madasu³

et al. 2017

Orient. J. Chem

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A simple, green and multi component, one pot synthesis of 14-Aryl-14H-dibenzo[a, j]xanthene derivatives by condensation of aryl aldehydes with 2-naphthol using magnetically separable and recyclable heterogeneous catalyst nano nickel cobalt ferrite (Ni 0.5 Co 0.5 Fe 2 O 4 ), has been described. In addition, a one-pot three component condensation of aryl aldehydes, 2-naphthol and dimedone has been developed to furnish 12-Aryl-8, 9, 10, 12-tetrahydrobenzo[a]xanthene-11-one derivatives in good to excellent yields under the same reaction conditions. The main advantage of this method is the nano catalyst can be reused up to five reaction cycles without losing the catalytic activity.

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“…Benzoxanthenes have also been utilized as antagonists for paralyzing action of zoxazolamine (Saint-Ruf et al 1975) and in photodynamic therapy (Ion 1997). Due to their wide range of interesting biological and therapeutic properties, many compounds related to benzoxanthene have been reported (Knight and Little 2001;Jha and Beal 2004;Bekaert et al 1992;Ohishi et al 2001;Gong et al 2009;Nandi et al 2009). Based on our previous studies (Wang et al 2012(Wang et al , 2013, in this article, we report two new dibenzoxathene isomers 2-ONEDDX 3 (2-ONEDDX = 1-oxo-2-(N-methyl-aminocarbonyl)-13c-methoxyl-1,13c-dihydroxyl-dibenzo[a,kl]xanthene) and 8-ONEDDX 4 (8-ONEDDX = 1-oxo-8-(N-methylaminocarbonyl)-13c-methoxyl-1,13c-dihydroxyl-dibenzo[a,kl]-xanthene).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Structure, DNA/Protein Binding, Cytotoxicity, Apoptosis, Reactive Oxygen Species, and Mitochondrial Membrane Potential of Dibenzoxanthenes Derivatives

Yang

Han

et al. 2015

J Membrane Biol

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Two dibenzoxanthene isomers 3 and 4 were synthesized and characterized. The crystal structures of the two compounds were solved by single-crystal X-ray diffraction. Binding of two compounds with calf thymus DNA (CT DNA) and BSA (bovine serum albumin) has been thoroughly investigated by UV-Vis and fluorescence spectroscopy. The DNA-binding constants were determined to be 2.51 (± 0.09) × 10(3) for compound 3 and 4.55 (± 0.10) × 10(3) for compound 4. Two compounds can cleave pBR322 DNA upon irradiation. Significant nuclear damages of BEL-7402 cells were observed with compound treatment in a comet assay. The cytotoxicity in vitro was investigated by MTT method. These compounds have been found to induce nuclear condensation and fragmentation in BEL-7402 cells. The two compounds can enhance intracellular reactive oxygen species and decrease the mitochondrial membrane potential. The compounds activated caspase-3 and caspase-7, down-regulated the expression levels of anti-apoptotic protein Bcl-2, and up-regulated the expression levels of pro-apoptotic protein Bax. These compounds induce apoptosis of BEL-7402 cells through an ROS-mediated mitochondrial dysfunction pathway.

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New total synthesis of bikaverin

Cited by 119 publications

References 4 publications

Silica supported perchloric acid: an efficient catalyst for the synthesis of 14-aryl-14H-dibenzo[a,i]xanthene-8,13-diones

Silica supported perchloric acid: an efficient catalyst for the synthesis of 14-aryl-14H-dibenzo[a,i]xanthene-8,13-diones

Nano Nickel-Cobalt Ferrite Catalyzed One Pot Synthesis of 14-Aryl-14H-Dibenzo[A, J]Xanthenes and 12-Aryl-8, 9, 10, 12-Tetrahydrobenzo[A]Xanthene-11-One Derivatives

Synthesis, Molecular Structure, DNA/Protein Binding, Cytotoxicity, Apoptosis, Reactive Oxygen Species, and Mitochondrial Membrane Potential of Dibenzoxanthenes Derivatives

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