Synthesis and antiallergic activity of some mono- and disubstituted xanthone-2-carboxylic acids

Pfister, J. R.; Ferraresi, R. W.; Harrison, I. T.; Rooks, Wendell H.; Fried, J. H.

doi:10.1021/jm00205a014

Cited by 17 publications

(13 citation statements)

References 6 publications

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“…To this end, the structure-activity relationship (SAR) studies are currently available for the following activities: tuberculostatic [16,[85][86][87], antimycotic [88], antimalarial [89,90], antiplatelet [91][92][93][94], antithrombotic [95], antiinflammatory [54,96,97], antiallergic [13,22,24], antitumor [7,17,81,[98][99][100][101][102][103][104][105][106][107], antimutagenic [108][109][110], and antioxidant [38,43,55]. Furthermore, SAR studies have been also developed in the field of adrenergic blocking agents [7,11] [112], leukotriene (LT) B4 receptors blocking agents [113][114][115], as well as for effects on several enzymes, such as acetylcholinesterase [116,117], aldose reductase [118], aromatase …”

Section: Biological Activitiesmentioning

confidence: 99%

Xanthone Derivatives: New Insights in Biological Activities

Pinto¹,

Sousa

Nascimento

2005

CMC

431

224

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Xanthones or xanthen-9H-ones (dibenzo-gamma-pirone) comprise an important class of oxygenated heterocycles whose role is well-known in Medicinal Chemistry. The biological activities of this class of compounds are associated with their tricyclic scaffold but vary depending on the nature and/or position of the different substituents. In this review, an array of biological/pharmacological effects is presented for both natural and synthetic xanthone derivatives, with an emphasis on some significant studies on structure-activity relationships. The antitumor activity of some xanthones as well as the related targets, particularly PKC modulation studies, is also discussed in detail. Examples of the "hit" compounds involved in cancer therapy, namely DMXAA, psorospermin, mangiferin, norathyriol, mangostins, and AH6809, a prostanoid receptor antagonist, are also mentioned. Finally, a historical perspective of these xanthonic derivatives, their relevance as therapeutic agents and/or their uses as pharmacological tools and as extract components in folk medicine are also highlighted.

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Section: Biological Activitiesmentioning

confidence: 99%

Xanthone Derivatives: New Insights in Biological Activities

Pinto¹,

Sousa

Nascimento

2005

CMC

431

224

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“…Their struc tures and biological activity have already been de scribed [17,18]. Sodium cromoglycate, 5,5'-[(2-hydroxy-1,3-propane)bis(oxy)]bis[4-oxo-4H-l-benzopyran-2-carboxylic acid], disodium salt (VIII), 6,7,8,9-tetrahydro-5-hydroxy-4-oxolo propyl-4H-naphtho(2,3-6)pyran-2-carboxylic acid, sodium salt (IX), 5-(hydroxypropoxy)-4-oxo-4H-l-benzopyran-2-carboxylic acid, sodium salt (X), 6,8-di(l,l-dimethylethyl)-4-oxo-4H-l-benzopyran-2-carboxylic acid, sodium salt (XI) and 8-allyl-5-(3-methylbutoxy)-4-oxo-4H-l-benzopyran-2-carboxylic acid, sodium salt (XII) were supplied by Fisons Ltd., Pharmaceutical Division, Loughborough, England.…”

Section: Antiallergic Compoundsmentioning

confidence: 99%

Glycosphingolipid Clustering and Mast Cell Degranulation

Curtain¹,

Looney²,

Smelstorius³

1981

Int Arch Allergy Immunol

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It was shown using spin-labelled probes that challenge of sensitized rat peritoneal mast cells results in clustering of sphingolipids located in the outer leaflet of the plasma membrane bilayer. This clustering is partially inhibited by antiallergic drugs of the chromone type. It is hypothesized that the sphingolipid clustering may be involved in the Ca⁺⁺ gate mechanism which is associated with anaphylactically-induced mast cell degranulation.

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“…Several analogues of 9-oxo-9 H -xanthene-2-carboxylic acid ( 162 ) have been synthesized through the years, holding different patterns of substitution (Table 1) [151,153,154,155,156,157,158,159,160,161,162,163,164,165,166]. The synthetic methodologies used to obtain these analogues were via diaryl ether and benzophenone intermediates, and through the derivatization of xanthones as building blocks.…”

Section: Synthetic Carboxyxanthone Derivativesmentioning

confidence: 99%

“…In 1978, a series of other 9-oxo-9 H -xanthene-2-carboxylic acid analogues ( 206 – 231 ) were specifically developed for antiallergic activity, by Pfister et al [158], using different methodologies. Analogues 206 – 210 were obtained using carboxyxanthone 162 as a building block to obtain xanthene-2-carboxylic acid through a Huang-Minlon reduction, followed by esterification of the carboxylic acid, and Friedel-Crafts acylation with an acyl halide.…”

Section: Synthetic Carboxyxanthone Derivativesmentioning

confidence: 99%

“…Analogues 206 – 210 were obtained using carboxyxanthone 162 as a building block to obtain xanthene-2-carboxylic acid through a Huang-Minlon reduction, followed by esterification of the carboxylic acid, and Friedel-Crafts acylation with an acyl halide. The obtained compound was then oxidized with Jones reagent, and the saponification of the ester provided the desired compounds [158]. 7-Mercapto-9-oxo-9 H -xanthene-2-carboxylic acid ( 211 ) was prepared through derivatization of methyl 7-hydroxy-9-oxo-9 H -xanthene-2-carboxylate with dimethylcarbamothioic chloride, followed by thermal rearrangement and base hydrolysis.…”

Section: Synthetic Carboxyxanthone Derivativesmentioning

confidence: 99%

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Carboxyxanthones: Bioactive Agents and Molecular Scaffold for Synthesis of Analogues and Derivatives

et al. 2019

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Xanthones represent a structurally diverse group of compounds with a broad range of biological and pharmacological activities, depending on the nature and position of various substituents in the dibenzo-γ-pyrone scaffold. Among the large number of natural and synthetic xanthone derivatives, carboxyxanthones are very interesting bioactive compounds as well as important chemical substrates for molecular modifications to obtain new derivatives. A remarkable example is 5,6-dimethylxanthone-4-acetic acid (DMXAA), a simple carboxyxanthone derivative, originally developed as an anti-tumor agent and the first of its class to enter phase III clinical trials. From DMXAA new bioactive analogues and derivatives were also described. In this review, a literature survey covering the report on carboxyxanthone derivatives is presented, emphasizing their biological activities as well as their application as suitable building blocks to obtain new bioactive derivatives. The data assembled in this review intends to highlight the therapeutic potential of carboxyxanthone derivatives and guide the design for new bioactive xanthone derivatives.

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Synthesis and antiallergic activity of some mono- and disubstituted xanthone-2-carboxylic acids

Cited by 17 publications

References 6 publications

Xanthone Derivatives: New Insights in Biological Activities

Xanthone Derivatives: New Insights in Biological Activities

Glycosphingolipid Clustering and Mast Cell Degranulation

Carboxyxanthones: Bioactive Agents and Molecular Scaffold for Synthesis of Analogues and Derivatives

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