One-Step Synthesis of Xanthones Catalyzed by a Highly Efficient Copper-Based Magnetically Recoverable Nanocatalyst (original) (raw)
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Synthetic approaches to biologically active xanthones: an update
Chemical Papers, 2020
Many xanthone structures show promising biological activities. Accordingly, a breadth of synthetic strategies toward xanthone derivatives have been developed. This review surveys these methods published from 2013 to 2019, and in an integrated manner details the biological activities of key xanthone structures. The review highlights the synthesis of xanthones via the classical and the modified Grover, Shah, and Shah reaction; the use of ytterbium, palladium, ruthenium, copper catalysis; the use of chromen-4-ones as building blocks; the use of the Friedel-Crafts reaction; Ullmann-ether coupling; metal-free oxidative coupling; intermolecular and intramolecular couplings; xanthone synthesis via the intermolecular Diels-Alder reaction; a novel decarboxylative aminocatalytic strategy; use of the Michael reaction, and the use of the Knoevenagel-Michael, Michael/Michael, Michael/Henry cycloadditions; and [4+2] cycloaddition.
From Natural Products to New Synthetic Small Molecules: A Journey through the World of Xanthones
Molecules, 2021
This work reviews the contributions of the corresponding author (M.M.M.P.) and her research group to Medicinal Chemistry concerning the isolation from plant and marine sources of xanthone derivatives as well as their synthesis, biological/pharmacological activities, formulation and analytical applications. Although her group activity has been spread over several chemical families with relevance in Medicinal Chemistry, the main focus of the investigation and research has been in the xanthone family. Xanthone derivatives have a variety of activities with great potential for therapeutic applications due to their versatile framework. The group has contributed with several libraries of xanthones derivatives, with a variety of activities such as antitumor, anticoagulant, antiplatelet, anti-inflammatory, antimalarial, antimicrobial, hepatoprotective, antioxidant, and multidrug resistance reversal effects. Besides therapeutic applications, our group has also developed xanthone derivatives w...
Expeditious multicomponent synthesis of xanthone dimers
Proceedings of The 22nd International Electronic Conference on Synthetic Organic Chemistry
Xanthones are a type of compound widely found in many natural products from plants, fungi, and lichens and are considered privileged structures. Frequently, xanthones occur in nature as dimers, which often exhibit singular and potent biological effects. Although diverse methods for the synthesis of monomeric xanthones are known, dimeric xanthones remain synthetically challenging targets. Reported syntheses of dimeric xanthones are very scarce, and invariably involve a large number of synthetic steps. We have recently developed a multicomponent synthesis of xanthones starting from 3-carbonylchromones, isocyanides, and dienophiles. Here we report a similar one-pot tandem procedure, involving a [4+1]-[4+2] cycloaddition, that readily affords dimeric xanthones and dihydroxanthones, which are structurally similar to bioactive ergochromes.
One-pot synthesis of xanthones using a novel copper-based magnetically recoverable nanocatalyst
Proceedings of The 17th International Electronic Conference on Synthetic Organic Chemistry, 2013
A versatile and straightforward strategy to construct a xanthone skeleton via an intermolecular catalytic coupling of 2-substituted benzaldehydes and a wide range of phenols has been developed. For this purpose, a novel and magnetically recoverable catalyst consisting of copper nanoparticles on nanosized silica coated maghemite in absence of ligand is presented. The reaction proceeds smoothly without the need to preactivate the aldehyde carbonyl group. It can tolerate various functional groups and provides an efficient protocol for the generation of a small library of xanthones in high yield.
Asian Journal of Pharmaceutical and Clinical Research, 2018
Xanthones are one of the biggest classes of compounds in natural product chemistry. A number of xanthones have been isolated from natural sources of higher plants such as fungi, ferns, and lichens. Synthetic analogs of xanthones have shown a large number of pharmacological properties such as antioxidant, anti-inflammatory, antidiabetics, antihistamine, antitumoral, antiulcer, and algicidal. Moreover, they also find usages in photodynamic therapy, laser technology, and dyes. This review lays stress on various solvents, catalyst and synthetic route for synthesis of xanthones, benzoxanthones analogs. The review has also focused on the classifications of xanthone as well as extensively studied biological properties of the xanthones and benzoxanthones analogs.
Recent progress in biologically active xanthones
Journal of chemical and pharmaceutical research, 2016
Xanthone is a novel and pharmacologically important oxygen containing hetrocyclic ring exhibiting variety of potent biological activities. This fused tricyclic ring is derived naturally from the plants of Bonnetiaceae and Clusiaceae family as well as synthesized by employing various synthetic protocols. Their wide range of reported therapeutic attributes include α-glucosidase inhibition, anti-cancer, anti-oxidant, anti-asthmatic, anti-convulsant, xanthine oxidase inhibition and anti-microbial. Among these attributes, anti-cancer and anti-oxidant potential are comprehensively studied as evidenced by number of research papers. Although, there is no marketed formulation containing xanthone derivatives except some herbal formulations, their medicinal properties can not be neglected at all. Promising activities revealed by these compounds chains their use and places them ahead as potential drug candidates for the future studies. Therefore, the present review article is entirely an assemb...
Recent Insights into the Biosynthesis and Biological Activities of Natural Xanthones
Current Medicinal Chemistry, 2010
This review focuses on recent advances in our understanding of the complex biosynthetic pathways and diverse biological activities of naturally occurring xanthones. The biosynthesis section covers studies published from 1989 to 2008 on xanthone production in plants and fungi, while the bioactivity review presents tabulated activities of more than 250 xanthones described in studies published from 2001 to 2008, together with structural information and indications of their wide-ranging potential uses as pharmacological tools. A large number of relevant papers have been published on these subjects (128 cited here), illustrating the diversity of the xanthones and their possible uses.
Recent Insights into the biosynthesis and biological activites of natural Xanthones
This review focuses on recent advances in our understanding of the complex biosynthetic pathways and diverse biological activities of naturally occurring xanthones. The biosynthesis section covers studies published from 1989 to 2008 on xanthone production in plants and fungi, while the bioactivity review presents tabulated activities of more than 250 xanthones described in studies published from 2001 to 2008, together with structural information and indications of their wide-ranging potential uses as pharmacological tools. A large number of relevant papers have been published on these subjects (128 cited here), illustrating the diversity of the xanthones and their possible uses.
Helvetica Chimica Acta, 1974
(silica gel, C,H,/EtOAc 9 : 1) 0.11 g of oily N-benzyl, N-(cis-3-phenylallyl)-toluenesulfonamide ( 5 ) . -IR. (Nujol) : 13.50, 1170, no band a t 940. -lH-NMR. (100 MHz) : 2.41 (3 H, s) ; 3.98 ( 2 H, d x d , J = 2 Hz and 6.5 Hz); 4.26 (2 H, s ) ; 5.38 ( l H , d x t , J = 11.5 Hz and 6.5 Hz); 6.42 ( l H , d x t , , T = 11.5 Hz and 1.5 Hz); 6.8-7.4 (12 H ) ; 7.66 ( 2 H, d , J = 8 Hz).