Xanthene Derivatives Research Articles

Adsorption behavior and corrosion inhibitive characteristics of newly synthesized cyano-benzylidene xanthenes on copper/sodium hydroxide interface: Electrochemical, X-ray photoelectron spectroscopy and theoretical studies

Elegant process for synthesis of 3-(7H-dibenzo[c,h]xanthen-7-yl)benzaldehyde (3), as new starting material to create a set of novel xanthene analogues, 2-(3-(7H-dibenzo[c,h]xanthen-7-yl)benzylidene)malononitrile (4), 3-(3-(7H-dibenzo[c,h]xanthen-7-yl)phenyl)-2-cyanoacrylic acid (5), and Ethyl-3-(3-(7H-dibenzo[c,h]xanthen-7-yl)phenyl)-2-cyanoacrylate (6), was achieved starting with available materials under mild conditions. Various concentrations (ca. 0.1–1.0 mM) of the synthesized cyano-benzylidene xanthene derivatives, namely compounds 3–6, were tested as inhibitors to control copper corrosion in alkaline solutions employing polarization and electrochemical impedance spectroscopy (EIS) measurements. Results revealed that the four studied xanthenes derivatives served as efficient (mixed-type) inhibitors. The inhibition efficiency increased with increase in inhibitor concentration.The inhibition performance of studied compounds varied according to their chemical structures. The best inhibitor, compound (5), achieved a maximum inhibition efficiency of 98.7% (calculated from corrosion current densities) and ~ 95% (estimated from charge-transfer resistance values) at a concentration of 1.0 mM. The morphology of the corroded and inhibited copper surfaces was studied by scanning electron microscopy (SEM). The adsorption of the inhibitor molecules was confirmed by high-resolution X-ray photoelectron spectroscopy (XPS) profiles. XPS data were used to compare the inhibition efficiencies exhibited by studied compounds. The oxidation rate of the Cu surface was found to be frivolous, referring to high inhibition efficiency, only in the presence of inhibitor (5), and Cu0 share is 87% of all copper components. The shares of Cu0 were significantly reduced to 43%, 26% and 20% for inhibitors (3), (4) and (6), respectively. These findings go parallel with the results obtained from electrochemical measurements. The quantum-chemical calculations of the investigated molecules were performed to support electrochemical findings, and their correlations with the inhibition efficiency of the synthesized compounds were discussed.

Nano-ZnO Impregnated on Starch—A Highly Efficient Heterogeneous Bio-Based Catalyst for One-Pot Synthesis of Pyranopyrimidinone and Xanthene Derivatives as Potential Antibacterial Agents

A new method has been proposed for the synthesis of pyranopyrimidinone and xanthene derivatives using zinc oxide–starch nanocomposite as catalyst under microwave irradiation. The ZnO–starch nanocomposite was characterized by X-ray diffraction and scanning electron microscopy data, and the size of the ZnO-starch nanocomposite particles was estimated at 70–90 nm. The catalyst was used in the three-component condensation of aromatic aldehydes with barbituric acid and malononitrile and the 1:2 condensation of aromatic aldehydes with naphthalen-2-ol to obtain pyranopyrimidinone and xanthene derivatives, respectively. The catalyst can be reused several times without loss of catalytic activity. The proposed procedure utilizes affordable and inexpensive materials, provides excellent yields in short reaction time, and is eco-friendly, which makes it more economic than conventional methods. The antibacterial activity of the synthesized compounds was evaluated against M. luteus and P. aeruginosa.

Calcined Layered Double Hydroxides: Catalysts for Xanthene, 1,4-Dihydropyridine, and Polyhydroquinoline Derivative Synthesis.

This work is generally focused on the synthesis of NiFeTi-layered double hydroxides (LDHs) using a hydrothermal route, which were calcined at various temperatures (varying from 200 to 600 °C). The synthesized materials were physicochemically characterized. X-ray diffraction results revealed the loss of the layered structure on calcination resulting in the formation of layered double oxides (LDOs) or mixed metal oxides, which was also supported by Fourier transform infrared studies. Scanning electron microscopy results also show loss of the layered structure and the creation of LDOs on increasing the temperature. These LDOs were tested as the catalysts for the synthesis of biologically significant xanthene, 1,4-dihydropyridine, and polyhydroquinoline derivatives. Among all, NiFeTi LDH calcined at 600 °C proved to be the best catalyst for the synthesis of these derivative compounds under optimized conditions. The advantages obtained were excellent yields in a lesser reaction time. Stability and reusability were also assessed; the catalyst was stable even after five cycles. Furthermore, the memory effect of the obtained NiFeTi CLDH calcined at 600 °C confirms that the material so formed is a calcined state of LDH itself. High catalytic efficiency, easy fabrication, and recycling ability of NiFeTi CLDH calcined at 600 °C make it a potential catalyst for the synthesis of xanthene, 1,4-dihydropyridine, and polyhydroquinoline derivatives.

Novel tandem Knoevenagel-Michael condensation product of naphtho[2,1-b]furan-2-carbaldehyde with dimedone: Synthesis, spectroscopic and crystal structure studies

Abstract 2,2′-Napthfuranyl bis(3‑hydroxy-5,5-dimethyl-2-cyclohexene-1-one) (2) was obtained in one pot via condensation between naphtho[2,1-b]furan-2-carbaldehyde (1) and dimedone. Instead of the Knoevenagel condensation product, (2) was obtained via tandem Knovenegel-Michael reaction. The reaction went effortlessly even in the absence of a strong base/catalyst and in short duration. Cyclisation of (2) to yield the expected xanthene derivative did not occur even after the reflux was carried out with Conc. HCl and H2SO4. The crystal structure of (1) was studied by single crystal X-ray diffraction technique (SCXRD). Further, (2) was characterized by FTIR, 1H & 13C NMR, mass spectral analysis, and, further by SCXRD. Crystal structure of (1) features several CH…O, CH…π and many π…π interactions resulting in a complex three dimensional (3D) architecture, while, in (2), whose molecular conformation is stabilized by two intramolecular OH…O hydrogen bonds, CH…O and π…π interactions form 1D ribbon like architecture. Hirshfeld surface analyses were also performed.

Quantitative structure–activity relationships of xanthen-3-one and xanthen-1,8-dione derivatives and design of new compounds with enhanced antiproliferative activity on HeLa cervical cancer cells

Xanthene derivatives have become a group of molecules of great importance in discovering of new anticancer drugs. Recent studies of our group performed on xanthen-3-one and xanthen-1,8-dione derivatives have shown their antiproliferative activity on HeLa cervical cell lines. Obtained IC50 values together with calculated molecular descriptors were subjected to Quantitative Structure–Activity Relationship (QSAR) study in order to identify the most relevant molecular features responsible for the observed antiproliferative activity of compounds. Partial least square statistical method and the same training and test set were used to obtain statistical parameters for internal and external validation in 2D- and 3D-QSAR study. The obtained QSAR models have shown next results: 2D-QSAR: R 2 = 0.741, Q 2 = 0.792, R 2 pred = 0.875 and 3D-QSAR: R 2 = 0.951, Q 2 = 0.830, R 2 pred = 0.769. Based on the performed QSAR analysis and calculated ADMET properties, novel xanthene derivatives with enhanced antiproliferative activity were designed. Communicated by Ramaswamy H. Sarma

Novel benzo[b]xanthene derivatives: Bismuth(III) triflate-catalyzed one-pot synthesis, characterization, and acetylcholinesterase, glutathione S-transferase, and butyrylcholinesterase inhibitory properties.

In this study, 3,4-dihydro-12-aryl-1H-benzo[b]xanthene-1,6,11-(2H,12H)trione compounds were obtained through one-pot condensation of various substituted aromatic aldehydes, 2-hydroxy-1,4-naphthoquinone, and dimedone in the presence of Bi(OTf)3 as a green and reusable catalyst. The structural characterization of these novel substituted benzo[b]xanthenes was performed by spectroscopic methods, and their inhibitory actions against butyrylcholinesterase (BChE), acetylcholinesterase (AChE), and glutathione S-transferase (GST) were investigated. GST is an enzyme responsible for removing toxic molecules during Phase II reactions in the detoxification mechanism. The AChE and BChE enzymes, which are called cholinesterases, are among the enzymes that occur especially during dementia such as brain damage or Alzheimer's disease. Inhibition effects of the benzo[b]xanthene derivatives on AChE, BChE, and GST were found at the millimolar level. The best inhibitor for GST is compound 4a (31.18 ± 6.13 mM), for AChE, it is compound 4d (28.16 ± 3.46 mM), and for BChE, it is compound 4f (36.24 ± 3.19 mM). Compound 4a inhibited the dimerization of GST subunits, and compounds 4d and 4f directly inhibited the catalytic activity by interacting with the catalytic active site or a related site of the AChE and BChE enzymes, respectively.

Functionalized magnetic PAMAM dendrimer as an efficient nanocatalyst for a new synthetic strategy of xanthene pigments

A green protocol has been developed for preparation of the wide variety of colored xanthene derivatives using a new efficient magnetic solid acid catalyst bearing polyamidoamine dendrimer moiety as a nanoscopic compound. Dendrimers, highly symmetric molecules around a core and 3D spherical morphology, show interesting traits based on their functionalized groups on the branched surface. They can be designed to provide water soluble structures or pseudo-active sites of biomolecules. The catalyst was assembled via a polyamidoamine dendrimer immobilized on the surface of γ-Fe2O3 followed by the sulfonylation of the amine groups by chlorosulfonic acid resulting in γ-Fe2O3@PAMAM-SO3H. Herein, PAMAM dendrimer with repeating amine/amide branches as catchable sites of sulfonic acid groups was introduced as transformer of homogeneous to heterogeneous acidic catalysts. The physicochemical properties of synthesized catalyst were studied using by FT-IR, FE-SEM, XRD, VSM, EDS, TGA/DTG, and TEM. Finally, the catalytic activity of γ-Fe2O3@PAMAM-SO3H was evaluated for the preparation of xanthene derivatives via a one-pot, three components reaction of aromatic aldehydes with i) β-naphthol, ii) cyclic 1,3-dicarbonyl, iii) β-naphthol and cyclic 1,3-dicarbonyl compounds, iv) 2-hydroxy-1,4-naphthoquinone, leading to the eco-riendly preparation of the target compounds in good to excellent yields. The catalyst could be easily recycled for at least five consecutive runs without significant loss in its catalytic activity.

One-pot synthesis of biologically important xanthene derivatives using [(Et3 N)2 SO][HSO4 ]2 as a novel and green IL-based catalyst under solvent-free conditions

One-pot synthesis of biologically important xanthene derivatives using [(Et3 N)2 SO][HSO4 ]2 as a novel and green IL-based catalyst under solvent-free conditions

Mono Dispersable Water-Soluble Iron Sulfide Nanoclusters: Synthesis, Characterization and Catalytic Application for Highly Efficient Synthesis of Xanthene Derivatives

In this manuscript, we have synthesized Iron sulfide nanoclusters (FeSNCs) by precipitation reaction between ferric chloride (FeCl3 · 6H2O) and thiourea with sodium borohydride (NaBH4) as a reducing agent at room temperature in water. These nanoclusters are synthesized within two minutes. The morphology and size of these synthesized FeSNCs were confirmed from transmission electron microscopy (TEM) and scanning electron microscopy (SEM). TEM and SEM data showed that the average diameters of these FeSNCs are around 70 nm. The Power X-ray diffraction (XRD) patten of the FeSNCs clearly showed the crystalline nature of these nanoclusters. Vibrating sample magnetometer (VSM) experiment showed that these nanoclusters are ferromagnetic in nature having high magnetization (20 emu/g). The nitrogen adsorption isotherm of FeSNCs confirmed the porous nature. These well characterized FeSNCs were further utilized as a catalyst for the synthesis of 9-aryl-1,8-dioxooctahydroxanthenes and 14-substituted-14H-dibenzo[a, j] xanthene derivatives. It is observed that the catalytic activities of FeSNCs are much better than the other reported heterogeneous and homogeneous catalysts. After completion of the reaction, FeSNCs are separated from the reaction mixture with the help bar magnet, washed and reused for the next catalytic reaction. Current method offers several advantages over other reported methods such as excellent yields, short reaction times, simple reaction procedure, and reusability of the catalyst upto five times without any significant loss in its activity.

Et3NH][HSO4]-mediated efficient synthesis of novel xanthene derivatives and their biological evaluation

A series of novel 2-chloro quinoline incorporated xanthene derivatives were synthesized by using various 2-chloro 3-formyl quinoline, dimedone and triethylammonium hydrogen sulfate [Et3NH][HSO4] as a catalyst as well solvent to give good to excellent yields. All the xanthene compounds were investigated for their in vitro antimycobacterial activity against M. tuberculosis H37Ra (MTB) and M. bovis BCG strains. Among the synthesized compounds 3a, 3c, 3d, 3e, 3g, 3h and 3k were highly potent against both the strains. Most of the active compounds were non-cytotoxic against THP-1, HCT-116, A549 and MCF-7 cell lines. Most active compounds were having higher selectively index which suggested that these compound were highly potent.

An efficient heterogeneous iron oxide nanoparticle catalyst for the synthesis of 9-substituted xanthene-1,8-dione

An efficient and simple method for the synthesis of xanthene derivatives by using iron oxide nanoparticles (NPs) as a catalyst has been investigated. Synthesis of 9-substituted xanthene-1,8-dione derivatives involves one-pot reaction of dimedone and aldehyde in the presence of iron oxide nanoparticles using polar protic ethanol as a solvent. Interestingly, this catalyst has been recovered by simple filtration and reused for up to five cycles without much loss of its productivity. The merits of this protocol are cost-effectiveness of the catalyst, having no harmful side products, simple process, short reaction time, convenient product isolation and potential yields.

(Aza,thio)xanthenylated amines and imines: synthesis, properties, and biological activity

The review addresses the synthetic potential of cations or hydrols of (aza,thio)xanthenes in reactions with primary and secondary amines and imines. The diversity of reaction pathways that depend on the structures of amines and imines is discussed. Biological activity of (aza,thio)-xanthene derivatives is considered.

Tamarind water catalyzed improved synthesis of 2,2ʹ-arylmethylenebis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) derivatives: A green approach

The reaction of 5,5-dimethyl-1,3-cyclohexanedione (dimedone) with various aromatic aldehydes catalyzed by tamarindwater produces 2,2ʹ-arylmethylenebis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) derivatives in 85-98% yield underwater bath heating at 60°C. Xanthene derivatives as cyclized products have not been obtained by this procedure.This method provides several advantages such as environmental friendliness, high yields and simple work-up procedure.The product is purified by simple filtration followed by crystallization with ethanol and drying processes.

One-pot three-component synthesis of 1,8-dioxooctahydroxanthenes and 14-Aryl-14Hdibenzo[a,j]xanthenes using a new nanostructure zeolite

A new modified zeolite containing Fe nanoparticles loaded in zeolite X (Fe-X) has been synthesized and characterized by FT-IR, XRD, EDX and SEM techniques and its catalytic activity has been investigated in the synthesis of two series of xanthene derivatives. We have described an efficient and novel method using Fe-X as a new and reusable catalyst for the synthesis of 1,8-dioxooctahydroxanthenes and 14-aryl-14H-dibenzo[a,j]xanthenes derivatives from one-pot three-component condensation of aromatic aldehyde and dimedone or β-naphthol under solvent-free conditions. The significant advantages of the present method are high yields of products, short reaction time, easy separation of the catalyst from the reaction mixture, easy product isolation, solvent-free condition and reusability of the catalyst. A new modified zeolite containing Fe nanoparticles loaded in zeolite X has been synthesized, characterized and applied in the synthesis of two series of xanthene derivatives.

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Structure-Bioactivity Relationship Study of Xanthene Derivatives: A Brief Review.

Over the last decades, several heterocyclic derivatives compounds have been synthesized or extracted from natural resources and have been tested for their pharmaceutical activities. Xanthene is one of these heterocyclic derivatives. These compounds consist of an oxygen-containing central heterocyclic structure with two more cyclic structures fused to the central cyclic compound. It has been shown that xanthane derivatives are bioactive compounds with diverse activities such as anti-bacterial, anti-fungal, anti-cancer, and anti-inflammatory as well as therapeutic effects on diabetes and Alzheimer. The anti-cancer activity of such compounds has been one of the main research fields in pharmaceutical chemistry. Due to this diverse biological activity, xanthene core derivatives are still an attractive research field for both academia and industry. This review addresses the current finding on the biological activities of xanthene derivatives and discussed in detail some aspects of their structure-activity relationship (SAR).

Brønsted Acidic Ionic Liquid: An Efficient and Reusable Catalyst for the Synthesis of Xanthenes Derivatives as Antimicrobial and Antioxidant Agents

In the present investigation, a mild, efficient and simple procedure has been developed for the synthesis of xanthene derivatives is described via three component condensation of aromatic aldehydes with β- naphthol or dimedone or mixture of β-naphthol and dimedone using Brønsted acidic ionic liquid, triphenyl(propyl-3-sulphonyl)phosphonium toluene-sulfonate under solvent-free conditions. The synthesized compounds were screened for antimicrobial activities against Gram-positive (Bacillus subtilis), Gram-negative (Pseudomonas aeruginosa) bacteria and fungus (Candida albicans). The antioxidant activities of these compounds were determined by DPPH scavenging free radical method. Present methodology has a number of advantages such as mild reaction condition, inexpensive catalyst, stable at room temperature and it was also found that this catalyst might be recovered quantitatively and reused without much loss of catalytic activity.

Selective DCP detection with xanthene derivatives by carbonyl phosphorylation.

Rhodamine derivatives (1-2) exhibited dual channel 'turn-on' photophysical signalling selectively with diethyl chlorophosphate (DCP) among various organophosphates (OPs), where the spiro-ring opening corresponds to the adduct formation through phosphorylation at their carbonyl O-spiro nucleophilic centres.

Pulsed laser ablated zeolite nanoparticles: A novel nano‐catalyst for the synthesis of 1,8‐dioxo‐octahydroxanthene and N‐aryl‐1,8‐dioxodecahydroacridine with molecular docking validation

There is an increasing interest in the synthesis of metal nanoparticles (NPs) from bulk metals using pulsed laser ablation in liquids (PLAL), as it offers an easy and simple synthesis route. In this work, zeolite NPs (molecular sieve 4A) were successfully synthesized by the PLAL technique, and characterized by X‐ray diffraction, scanning electron microscopy, Fourier transform infrared spectroscopy, transmission electron microscopy, field emission scanning electron microscopy, and high‐resolution transmission electron microscopy. Data obtained confirm the formation of the crystalline phase of zeolite. The synthesized catalyst (zeolite molecular sieve 4A) was used as an efficient and facile promotor for the synthesis of xanthene and acridine derivatives. Molecular docking of the synthesized compounds was validated using quinone reductase 2 (NQO2) and acridine orange as the ligand, with the synthesized molecules showing good drug–ligand interaction on the active site of NQO2, compared with that of acridine orange.

INTRODUCING AN EFFECTIVE NANOCATALYTIC FOR THE ONE-POT SYNTHESIS AND INVESTIGATION OF BIOLOGICAL PROPERTIES OF PYRANOPYRIMIDINONE AND XANTHENE DERIVATIVES

In this study, an effective method for the synthesis of pyranopyrimidinone and xanthene derivatives is introduced. In this method, zinc oxide-chitosan nanocomposite has been used as a catalyst and all reactions were performed under irradiated in a microwave oven at a power of 230W. The properties of zinc oxide-chitosan nanocomposite were characterized by X-ray diffraction (XRD), energy dispersive X-ray (EDAX) analysis and scanning electron microscopy (SEM). The results indicated that the size of zinc oxide-chitosan nanocomposite varies between 76–95 nm. The catalyst activity has maintained its activity after four runs. The main advantages of this method are; Eco-friendly procedure, catalytic synthesis of affordable and inexpensive materials, short reaction time, and excellent yields which makes it more economic than the other conventional methods. The antibacterial activity of the products was investigated using Minimum Inhibitory Concentration (MIC) and the Minimum Bactericidal Concentration (MBC) methods. Pyranopyrimidinone derivatives exhibit more antibacterial activity.