Ultrasound promoted synthesis of Nile Blue derivatives

Ultrasound irradiation was used for the first time towards the synthesis of new Nile Blue related benzo[a]phenoxazinium chlorides possessing isopentylamino, (2-cyclohexylethyl)amino and phenethylamino groups at 5-position of the heterocyclic system. The efficacy of sonochemistry was investigated with some of our earlier reported synthesis of benzo[a]phenoxazinium chlorides. This newer protocol proved competent in terms of reaction times and enhanced yields. Photophysical studies carried out in ethanol, water and simulated physiological conditions, revealed that emission maxima occurred in the range 644–656 nm, with high fluorescent quantum yields. Other attractive feature exhibited by these materials includes good thermal stability. These properties might be useful in the development of fluorescent probes for biotechnology.     

Molecular docking studies,biological evaluation and synthesis of novel 3-mercapto-1,2,4-triazole derivatives

Molecular Diversity - Synthesis of bioactive heterocyclic compounds having effective biological activity is an essential research area for wide-ranging applications. In this study, a conventional...     

Sonochemically assisted synthesis of zinc-doped maghemite

Nanoparticles of zinc-doped maghemite were prepared using ultrasonic radiation. As a precursor, a suspension of maghemite in an alkaline aqueous solution of zinc nitrate at pH 9 was sonicated. The zinc-doped maghemite nanoparticles were investigated by X-ray diffraction, Mössbauer spectroscopy, high-resolution electron microscopy (HREM) and SQUID magnetometry. The Mössbauer measurements, which cover the temperature range 4.2 K to room temperature, were acquired in zero field and an applied field of 5 T. The results show that by using ultrasound radiation, zinc Zn²⁺ can substitute for Fe³⁺ up to a composition close to zinc ferrite (ZnFe₂O₄), which has a random distribution of Fe³⁺ ions over both A and B sublattices in the spinel structure with an inversity parameter of δ = 0.322. This leads to a maximum saturation magnetization (M_s) of 64.1 emu/g at 300 K and 73.5 emu/g at 2 K.     

Design,synthesis and biological evaluation of novel flavone Mannich base derivatives as potential antibacterial agents

Molecular Diversity - A series of novel Mannich base derivatives of flavone containing benzylamine moiety was synthesized using the Mannich reaction. The results of antifungal activity are not...     

Novel ocotillol-derived lactone derivatives: design,synthesis, bioactive evaluation,SARs and preliminary antibacterial mechanism

A new series of ocotillol-derived lactone derivatives were designed and synthesized to consider their antibacterial activity, structure–activity relationships (SARs), antibacterial mechanism and in vivo antibacterial efficacy. Compound 6d, which exhibited broad antibacterial spectrum, was found to be the most active with minimum inhibitory concentrations (MICs) of 1–2 μg/mL against Gram-positive bacteria and 8–16 μg/mL against Gram-negative bacteria. The subsequent synergistic antibacterial tests displayed that 6d had the ability to improve the susceptibility of MRSA USA300, B. subtilis 168, and E. coli DH5α to kanamycin and chloramphenicol. This active molecule 6d also induced bacterial resistance more slowly than norfloxacin and kanamycin. Furthermore, compound 6d was membrane active and low toxic against mammalian cells, and it could rapidly inhibit the growth of MRSA and E. coli and did not obviously trigger bacterial resistance. Compound 6d also displayed strong in vivo antibacterial activity against S. aureus RN4220 in murine corneal infection models. Additionally, absorption, distribution, metabolism, and excretion properties of this type of compounds have shown drug-likeness with good oral absorption and moderate blood–brain barrier permeability. The obtained results demonstrated that ocotillol-derived compounds are a promising class of antibacterial agents worthy of further study.

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Synthesis, anticancer, and anti-inflammatory activity evaluation of methanesulfonamide and amidine derivatives of 3,4-diaryl-2-imino-4-thiazolines

Condensation of 3,4-diaryl-2-imino-4-thiazoli-nes 1a–j with methanesulfonyl chloride gave methanesulfonamide derivatives 2a–j. Condensation of 2-cyanopyrazine, 4-cyanopyridine, and 2-cyanopyridine with 3,4-diaryl-2- imino-4-thiazolines 1h–m in the presence of sodium methoxide afforded amidine derivatives 3a–j. Compounds 2a–j and 3a–j were screened against various human cancer cell lines (COLO-205, HEP-2, A-549, IMR-32) and their percentage growth inhibition profile determined at 1 × 10⁻⁵M. The anti-inflammatory activity of these compounds was assessed using the carrageenan-induced paw edema model. Compound 2i exhibited 34.7% anti-inflammatory activity at 50 mg/kg p.o., which is comparable to standard care drug phenyl butazone (37% activity at 50 mg/kg p.o.)     

Synthesis of deuterium-enriched sorafenib derivatives and evaluation of their biological activities

Molecular Diversity - Deuterium substitution has been widely known that can improve the pharmacokinetic profiles due to isotope effect. Herein, a series of deuterated sorafenib derivatives have...     

State of the art and recent advances in the ultrasound-assisted synthesis,exfoliation and functionalization of graphene derivatives

Sonochemistry, an almost a century old technique was predominantly employed in the cleaning and extraction processes but this tool has now slowly gained tremendous attention in the synthesis of nanoparticles (NPs) where particles of sub-micron have been produced with great stability. Following this, ultrasonication techniques have been largely employed in graphene synthesis and its dispersion in various solvents which would conventionally take days and offers poor yield. Ultrasonic irradiation allows the production of thin-layered graphene oxide (GO) and reduced graphene oxide (RGO) of up to 1 nm thickness and can be produced in single layers. With ultrasonic treatment, reactions were made easy whereby graphite can be directly exfoliated to graphene layers. Oxidation to GO can also be carried out within minutes and reduction to RGO is possible without the use of any reducing agents. In addition, various geometry of graphene can be produced such as scrolled graphene, sponge or foam graphene, smooth as well as those with rough edges, each serving its own unique purpose in various applications such as supercapacitor, catalysis, biomedical, etc. In ultrasonic-assisted reaction, deposition of metal NPs on graphene was more homogeneous with custom-made patterns such as core-shell formation, discs, clusters and specific deposition at the edges of graphene sheets. Graphene derivatives with the aid of ultrasonication are the perfect catalyst for various organic reactions as well as an excellent adsorbent. Reactions which used to take hours and days were significantly reduced to minutes with exceedingly high yields. In a more recent approach, sonophotocatalysis was employed for the combined effect of sonication and photocatalysis of metal deposited graphene. The system was highly efficient in organic dye adsorption. This review provides detailed fundamental concepts of ultrasonochemistry for the synthesis of graphene, its dispersion, exfoliation as well as its functionalization, with great emphasis only based on recent publications. Necessary parameters of sonication such as frequency, power input, sonication time, type of sonication as well as temperature and dual-frequency sonication are discussed in great length to provide an overview of the resultant graphene products.     

Sonochemistry: A good,fast and clean method to promote the synthesis of 5-arylidene-2,4-thiazolidinediones

The efficient synthesis of sixteen 5-arylidene-2,4-thiazolidinediones by aldol condensation reaction of 2,4-thiazolidinedione, mono- and di-substituted arenealdehydes and KOH using ultrasound irradiation is reported. The desired compounds were obtained in a few min (10–30 min) with moderate to good yields (25–81%).     

Diastereoselective multicomponent synthesis and anti-HSV-1 evaluation of dihydrofuran-fused derivatives

Enolizable 6-membered cyclic 1,3-dicarbonyls undergo an efficient and diastereoselective domino condensation/addition/heterocyclization reaction with arylaldehydes and phenacyl chloride, producing highly substituted dihydrofuran-fused derivatives. Ring size of the cyclic 1,3-dicarbonyls and the presence of at least one keto group are crucial to the reaction's success. The new compounds were evaluated in vitro for antiviral activity against herpes simplex virus type-1 (HSV-1). Interestingly, some of them appeared able to interfere with HSV-1 replication, without detection of cytotoxic effects.     

4H-benzochromene derivatives as novel tyrosinase inhibitors and radical scavengers: synthesis,biological evaluation,and molecular docking analysis

Molecular Diversity - A series of ethyl 2-amino-4H-benzo[h]chromene-3-carboxylate derivatives, having phenyl ring with diverse substituents at C4 position of 4H-benzochromene nucleus, were...     

Ultrasonic assisted synthesis of styrylpyridinium dyes: Optical properties and DFT calculations

The ultrasonic technique has received considerable attention in several fields; in particular, it gained rapid momentum in organic synthesis due to the larger reaction rates, milder reaction conditions, and better yields. We report herein a facile synthesis of a series of styrylpyridinium based dyes under ultrasonic irradiation. Within short reaction time (15 min) under ultrasonic irradiation, compared to normal laboratory conditions, (4–16 h), we can achieve good to excellent yields. The reaction time is shortened because ultrasound can accelerate the generation of the nucleophile of the pyridinium salt and subsequently a nucleophilic addition of an aldehyde followed by dehydration affords the styrylpyridinium dye, (Knoevenagel condensation). The photophysical properties of all compounds are comprehensively investigated in different solvents. All the compounds exhibit negative solvatochromism both in absorption and fluorescence emission spectra. Such behavior is due to the higher dipole moment of these molecules at the ground state. DFT calculations were performed to understand the electronic structure of the molecules. Our results show the high efficacy of sonochemistry over other methods for preparation of styrylpyridinium dyes.     

Sonochemical synthesis of nanocrystalline mercury sulfide, selenide and telluride in aqueous solutions

Nanocrystalline mercury chalcogenides HgE (E = S, Se, Te) were synthesized in a single step by a convenient, simple sonochemical method. Mercury nitrate, Hg(NO₃)₂, dissolved in 0.1 M ethylenediamine tetraacetic acid (EDTA), was used as the source of mercury and elemental chalcogenes, dissolved in a NaOH solution, as the sources of chalcogenide. The products were characterized by X-ray powder diffraction (XRD), transmission electron microscopy (TEM) and energy-dispersive X-ray spectroscopy (EDAX). The synthesis procedure is simple and uses less toxic reagents than the previously reported methods. The results showed that the complexing agent EDTA plays a crucial role in the process.     

Facile one-step sonochemical synthesis of ultrafine and stable fluorescent C-dots

This work describes a one-step synthesis of carbon dots (C-dots), which is carried out by sonication of polyethylene glycol (PEG-400) for 0.5–3 h. The effect of the various experimental parameters, such as sonication time, amplitude and temperature on the size and the fluorescence of the C-dots was studied. It was found that the average diameter of the C-dots is between 2 and 9 nm, depending on the preparation conditions. The highest quantum yield of emission was ∼16%. These high fluorescence properties of the C-dots could be used for bioimaging and for solar cell applications.     

Synthesis,spectral characterization,docking studies and biological activity of urea,thiourea, sulfonamide and carbamate derivatives of imatinib intermediate

Molecular Diversity - A series of new urea/thiourea derivatives 3a–j were synthesized by simple addition reaction of functionalized phenyl isocyanates/isothiocyanates 2a–j with...     

Effect of potassium monopersulfate (oxone) and operating parameters on sonochemical degradation of cationic dye in an aqueous solution

In this study, removal of Cresol Red (CR), a cationic triphenylmethane dye, by 300 kHz ultrasound was investigated. The effect of additive such as potassium monopersulfate (oxone) was studied. Additionally, sonolytic degradation of CR was investigated at varying power and initial pH. RC can be readily eliminated by the ultrasound process. The obtained results showed that. Sonochemical degradation of CR was strongly affected by ultrasonic power and pH. The degradation rate of the dye increased substantially with increasing ultrasonic power in the range of 20–80 W. This improvement could be explained by the increase in the number of active cavitation bubbles. The significant degradation was achieved in acidic conditions (pH = 2) where the color removal was 99% higher than those observed in higher pH aqueous solutions. The ultrasonic degradation of dye was enhanced by potassium monopersulfate (oxone) addition. It was found that the degradation of the dye was accelerated with increased concentrations of oxone for a reaction time of 75 min.     

Bis-spirochromanones as potent inhibitors of Mycobacterium tuberculosis: synthesis and biological evaluation

Molecular Diversity - On the basis of reported antimycobacterial property of chroman-4-one pharmacophore, a series of chemically modified bis-spirochromanones were synthesized starting from...     

Ultrasonic assisted synthesis of a tetrazine functionalized MOF and its application in colorimetric detection of phenylhydrazine

TMU-34(-2H), [Zn(OBA)(DPT)_0.5].DMF, has been sonochemically synthesized by applying H₂OBA, (4,4′-oxybis(benzoic acid)), as the dicarboxylate linker, and DPT, (3,6-di(pyridin-4-yl)-1,2,4,5-tetrazine), as pillar spacer. Sonication time, concentration of initial reagents, sonication power and molar ratio of pyridine as modulator has been optimized to synthesize nano powder of TMU-34(-2H) including uniform plate morphology. Nano TMU-34(-2H), can detect phenylhydrazine (PH) by color changing from pink to deep purple. As a comparison, nano and crystal samples of TMU-34(-2H) were treated to detect PH. Experiments show that nano TMU-34(-2H) has better detection limit and response time.     

Sonochemical synthesis of porous gold nano- and microparticles in a Rosette cell

We report the synthesis of Au nano- and microparticles that relies on α-D-glucose (C₆H₁₂O₆) as the reducer and stabilizer in a Rosette cell under 20 kHz ultrasound irradiation. The chemical and physical effects of ultrasonic irradiation on the synthesis were investigated. The results showed that an optimum pH is required for the formation of insoluble Au(0) particles. Upon irradiation, low pH yielded Au nanoparticles while high pH resulted in microparticles. The Au surface capping by α-D-glucose hydroxyl and carbonyl groups was confirmed by Fourier transform infrared (FT-IR) spectroscopy. X-ray diffraction (XRD) analysis indicated that the Au particles crystallize within the face-centered-cubic (FCC) cell lattice. Moreover, continuous sonication reduced larger amounts of the Au precursor compared to the intermittent mode. Furthermore, tuning sonication time and mode influences the particle size and porosity as characterized by scanning and transmission electron microscopy. Our results shed a new light into the importance of the experimental and ultrasound parameters in obtaining Au particles of desired features through sonochemistry.