A review on possible mechanisms of sonocrystallisation in solution

Nalesso, Silvia; Bussemaker, Madeleine; Sear, Richard P.; Hodnett, Mark; Lee, Judy

doi:10.1016/j.ultsonch.2019.04.020

Cited by 97 publications

(87 citation statements)

References 139 publications

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“…On the other hand, by using polar protic solvents (MeOH and 2‐propanol), the yield of the desired product was slightly improved in the silent process (Table , entries 9 and 11), whereas better yield was detected after 1 h of sonication (Table , entries 10 and 12). Because polar solvents have higher dielectric constants that could interact well with US irradiation, intense heating is produced . Ultrasound will, therefore, be used as a sustainable source of energy during the next experiments to promote the model reaction in polar protic solvents.…”

Section: Resultsmentioning

confidence: 99%

“…Pyridines are among the most important biochemical scaffolds with broader uses in the medicinal and pharmaceutical industries as well as intermediates in heterocyclic preparations . Among pyridine derivatives, dicyanopyridines act as ‘privileged skeleton’ owing to their prospective uses for therapy . These derivatives were recorded to serve as anti‐prion, human adenosine A2B receptor, antibacterial, anti‐cancer, and anti‐hepatitis B virus .…”

Section: Background and Originality Contentmentioning

confidence: 99%

“…Besides, US irradiation has many benefits, such as minimum energy usage, reduced waste production and atomic economy . Since US irradiation effectively couples the molecules in solution form, it is essential to choose the solvent to attain optimal reaction parameters . In sonosynthesis, almost all polar solvents (aprotic and protic) are considered to be beneficial.…”

Section: Background and Originality Contentmentioning

confidence: 99%

See 2 more Smart Citations

Design, Sonosynthesis, Quantum‐Chemical Calculations, and Evaluation of New Mono‐ and Bis‐pyridine Dicarbonitriles as Antiproliferative Agents

Arafa

Hussein

2020

Chin. J. Chem.

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of main observation and conclusion A highly efficient, simple, and clean single-step sonosynthetic procedure has been sophisticated for assembling new series of mono-and bis-pyridine dicarbonitriles from ketones, HCl, and tetracyanoethylene. The presented protocol is applicable for the preparation of a broad range of uniquely substituted pyridine dicarbonitriles and seems to be superior in comparison with other previously reported methods. The antiproliferative impact of the newly synthesized derivatives was screened towards three representative cancer cell lines (MCF-7, A549, and HCT116). Most of the evaluated derivatives showed a moderate to excellent anti-proliferative activity towards the selected cell lines. Of these, compounds 4h, 4k, 10, 12a, and 12b showed both potent anticancer activity (IC50<10 μM) and lower cytotoxic effect (IC50 > 58 μM) on non-tumorigenic cells (MCF-10A and NCM460), suggesting their promising potential to be lead molecules for future antitumor drug discovery. The structure-activity relationships have been also discussed. Moreover, quantum chemical studies based on Density Functional Theory (DFT) of the synthesized compounds were investigated and found to be consistent with the in vitro inhibitory activities. Results and DiscussionPreparation of 6-chloro-[2,2'-bipyridine]-4,5-dicarbonitrile (4a) by treatment of tetracyanoethylene (1, TCNE, 1.0 mmol), and 2-acetyl pyridine (2a, 1.0 mmol) with HCl (3.0 mL) was chosen as the template reaction (Scheme 1) under silent (70 o C) and ultra-502 www.cjc.wiley-vch.de

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Section: Resultsmentioning

confidence: 99%

Section: Background and Originality Contentmentioning

confidence: 99%

Section: Background and Originality Contentmentioning

confidence: 99%

See 1 more Smart Citation

Design, Sonosynthesis, Quantum‐Chemical Calculations, and Evaluation of New Mono‐ and Bis‐pyridine Dicarbonitriles as Antiproliferative Agents

Arafa

Hussein

2020

Chin. J. Chem.

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“…Other advantages induced by sonication are related to the possibility of controlling the crystal structure properties of the final product in nanomaterials syntheses [5]. For this reason, theoretical scientific research is currently directed towards the understanding of the physical phenomena involved in sonocrystallization mechanisms [6]. A major benefit of sonocrystallization appeared to be the induction of nucleation and therefore, crystallization improvements were operated for several organic compounds of low to medium molecular weight with the possibility of scaling up of this technology for industrial use [7].…”

Section: Introductionmentioning

confidence: 99%

Ultrasound-assisted Strecker synthesis of novel 2-(hetero)aryl-2-(arylamino)acetonitrile derivatives

Gál

Gaina

Petkes

et al. 2020

Beilstein J. Org. Chem.

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This work describes an efficient, simple, and ecofriendly sonochemical procedure for the preparation of new α-(arylamino)acetonitrile derivatives C-substituted with phenothiazine or ferrocene units. The synthetic protocol is based on the Strecker reaction of a (hetero)aryl aldimine substrate with trimethylsilyl cyanide (TMSCN) in poly(ethylene glycol) (PEG) solution. The advantages of the sonochemical versus the conventional α-(arylamino)acetonitrile synthesis are the significantly shorter reaction time (30 min instead of 72 hours), the higher purity and the easier separation of the product that precipitated from the reaction mixture in crystalline form as depicted by scanning electron microscopy (SEM) analysis. The single crystal X-ray diffraction analysis disclosed the arrangement of the α-(arylamino)acetonitrile molecules in the aggregated crystalline state as a racemic mixture. The mutagenic/antimutagenic potential for three representative derivatives containing phenothiazinyl, ferrocenyl, and phenyl units, respectively, was evaluated by the Ames Salmonella/microsome test using S. typhimurium TA98 and TA100 strains with and without metabolic activation. The preliminary screening results pointed out that the C-(hetero)aryl-α-(arylamino)acetonitrile derivatives can be considered genotoxically safe and possibly antimutagenic.

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“…In the sono-crystallization literature, Apfel's third rule has been satisfied. The application of ultrasound to influence the outcome of crystallization has been reported on many occasions [4,5] and shows particular benefits in the control of crystallization of pharmaceutical drug substances. The most widely reported application is controlled initiation of nucleation at supersaturation levels significantly below the conventional metastable zone limit.…”

Section: Introductionmentioning

confidence: 99%

Quantifying Ultrasound for Sono-crystallizatio

Forbes

Price

O'Leary

2019

2019 IEEE International Ultrasonics Symposium (IUS)

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The application of ultrasound to crystallization processes is a well-established technique employed to control the initiation of nucleation and therefore to achieve control over the crystal size and size distribution. In the context of Apfel's golden rules of cavitation: "Know thy liquid," "Know thy sound field" and "Know when something happens," the third rule has been satisfied. However, in order to link the applied ultrasonic energy to the enhanced process parameters, it is important to characterize the sound field and cavitation activity in the crystallization solvent. In order to better understand and design sono-crystallization experiments in the context of pharmaceutical manufacturing, measurements of acoustic emissions, broadband integrated voltage and focused beam reflectance measurements (FBRM) have been carried out in five typical crystallization solvents and water at a fundamental frequency of 40 kHz. The approaches taken have been to detect and measure cavitation activity as a function of ultrasonic power, allowing a comparison across the solvents.

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A review on possible mechanisms of sonocrystallisation in solution

Cited by 97 publications

References 139 publications

Design, Sonosynthesis, Quantum‐Chemical Calculations, and Evaluation of New Mono‐ and Bis‐pyridine Dicarbonitriles as Antiproliferative Agents

Design, Sonosynthesis, Quantum‐Chemical Calculations, and Evaluation of New Mono‐ and Bis‐pyridine Dicarbonitriles as Antiproliferative Agents

Ultrasound-assisted Strecker synthesis of novel 2-(hetero)aryl-2-(arylamino)acetonitrile derivatives

Quantifying Ultrasound for Sono-crystallizatio

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