Recent Advances in the Ultrasound-Assisted Synthesis of Azoles

Pizzuti, Lucas; Franco, Márcia Silvana Freire; Flores, Alex F. C.; Quina, Frank H.; Pereira, Cláudio M. P.

doi:10.5772/35171

Cited by 26 publications

(12 citation statements)

References 51 publications

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“…The preparation, yields and the 1 H- and 13 C-nuclear magnetic resonance (NMR) data of compounds 1 – 11 are reported in the literature [18,20]. In this work, the structures of compounds 1 – 11 were confirmed by High Resolution Mass Spectrometry (HRMS).…”

Section: Resultsmentioning

confidence: 71%

“…The 3,5-diaryl-4,5-dihydro-1 H -pyrazole-1-carboximidamides 1 – 11 were prepared according to the literature and characterized by 1 H, 13 C-NMR [18,20], and confirmed by HRMS. All solvents and reagents were obtained from Aldrich (Hamburg, Germany) and used without further purification.…”

Section: Methodsmentioning

confidence: 99%

“…In addition, there have been reports of the synthesis of a series of 5-aryl-1-carboxamidino-3-styryl-4,5-dihydro-1 H -pyrazole derivatives from the cyclocondensation of 1,5-diaryl-1,4-pentadien-3-ones and aminoguanidine hydrochloride and their application in the synthesis of new 2-(5-aryl-3-styryl-4,5-dihydro-1 H- pyrazol-1-yl)-4-(trifluoromethyl)pyrimidines [19]. Furthermore, the synthesis under mild conditions of novel 3,5-diaryl-4,5-dihydro-1 H -pyrazole-1-carboximidamides by the reaction of chalcones with aminoguanidine hydrochloride in KOH has been described [20]. In addition to the antioxidant capacity of pyrazoles [16,17] several potential applications should be investigated.…”

Section: Introductionmentioning

confidence: 99%

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Anti-Candida, Anti-Enzyme Activity and Cytotoxicity of 3,5-Diaryl-4,5-dihydro-1H-pyrazole-1-carboximidamides

et al. 2014

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Because of the need for more effective and less harmful antifungal therapies, and interest in the synthesis of new carboximidamides, the goal of this study was to determine the antifungal and anti-enzyme activities of some new pyrazole carboximidamides and their cytotoxicity. For this purpose, tests were performed to evaluate: minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC); production of proteinases and phospholipase, and cytotoxicity of the extracts. Data were analyzed by ANOVA and Tukey Tests (α = 5%). The results were: MIC and MFC ≥ 62.5 μg/mL (C. albicans, C. parapsilosis, C. famata, C. glabrata, and Rhodotorula mucillaginosa) and OPEN ACCESSMolecules 2014, 19 5807 MIC and MFC ≥ 15.6 μg/mL (C. lipolytica). The values of proteinase and phospholipase (Pz) of C. albicans before and after exposure to the compounds were: 0.6 (±0.024) and 0.2 (±0.022) and 0.9 (±0.074) and 0.3 (±0.04), respectively. These proteinase results were not significant (p = 0.69), but those of phospholipase were (p = 0.01), and 15.6 μg/mL was the most effective concentration. The cytotoxicity means were similar among the tests (p = 0.32). These compounds could be useful as templates for further development through modification or derivatization to design more potent antifungal agents. Data from this study provide evidence that these new pyrazole formulations could be an alternative source for the treatment of fungal infections caused by Candida. However, a specific study on the safety and efficacy of these in vivo and clinical trials is still needed, in order to evaluate the practical relevance of the in vitro results.

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Section: Resultsmentioning

confidence: 71%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Anti-Candida, Anti-Enzyme Activity and Cytotoxicity of 3,5-Diaryl-4,5-dihydro-1H-pyrazole-1-carboximidamides

et al. 2014

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“…[20] The ultrasound on the other hand is known to accelerate the reaction rate considerably affording the desired product within short reaction time. Moreover, ultrasound assisted reactions (i) are viewed as green approaches in organic synthesis, [21] (ii) play important role in waste minimization and reduction of energy requirements [22] and (iii) are useful for the development of new, cost effective and environmentally safe methodologies for the synthesis of various organic molecules. [23,24] We therefore decided to adopt ultrasound assisted method for the faster access of our target compounds based on B.…”

Section: Resultsmentioning

confidence: 99%

Sonochemical Synthesis of 6‐Substituted Indolo[3′,2′:4,5]pyrrolo[2,3‐b]quinoxaline Derivatives as Potential Cytotoxic Agents

Rao

Srilaxmi

Vardhini³

et al. 2020

ChemistrySelect

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In the current study, we have explored 6‐substituted indolo[3′,2′:4,5]pyrrolo[2,3‐b]quinoxaline derivatives as potential cytotoxic agents. These compounds were readily prepared via the reaction of 2‐chloro‐3‐(2‐chloro‐1H‐indol‐3‐yl)quinoxaline with an appropriate amine under ultrasound irradiation in good to acceptable yields. The in vitro testing of all these compounds against MDA‐MB‐231 and MCF‐7 cell lines using a cell‐based assay and then against SIRT1 (or sirtuin 1) using an enzyme‐based assay was performed. The compound 3 a [i. e. 6‐(4‐methoxybenzyl)‐6,7‐dihydroindolo[3′,2′:4,5]pyrrolo[2,3‐b]quinoxaline] showed promising growth inhibition of both MDA‐MB‐231 and MCF‐7 cell lines (61 and 54 % at 10 μM, respectively) and inhibition of SIRT1 (IC50∼2.09±0.40 μM in vitro). Moreover, molecular modelling studies indicated interaction of 3 a with several residues e. g. GLU345, ILE347, PHE273, ILE270, PHE312, PRO271, ILE279, ILE316 at the active site of SIRT1 with estimated total energy=−99.90 kcal/mol and the ADME prediction in silico suggested 3 a as a potential hit molecule.

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“…The use of ultrasound to accelerate chemical reactions has proven to be a particularly important tool for meeting the "Green" Chemistry goals of minimization of waste, reduction of energy and time requirements ("Green" principles # 6, 8 and 11). Thus, nowadays the applications of ultrasonic irradiation are playing an increasing role in chemical processes, especially in cases where classical methods require drastic conditions or prolonged reaction times [35]. The chemical effects of ultrasound in liquids systems are derived from the formation, growth and implosion of small bubbles that appears when the liquid is irradiated by ultrasound waves, phenomenon called "acoustic cavitation" [36].…”

Section: Background and Physical Principles Of Sonochemistrymentioning

confidence: 99%

Toward Greener Chemistry Methods for Preparation of Hybrid Polymer Materials Based on Carbon Nanotubes

Ávila‐Orta¹,

González‐Morones²,

Espinoza-González³

et al. 2013

Syntheses and Applications of Carbon Nanotubes and Their Composites

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Recent Advances in the Ultrasound-Assisted Synthesis of Azoles

Cited by 26 publications

References 51 publications

Anti-Candida, Anti-Enzyme Activity and Cytotoxicity of 3,5-Diaryl-4,5-dihydro-1H-pyrazole-1-carboximidamides

Anti-Candida, Anti-Enzyme Activity and Cytotoxicity of 3,5-Diaryl-4,5-dihydro-1H-pyrazole-1-carboximidamides

Sonochemical Synthesis of 6‐Substituted Indolo[3′,2′:4,5]pyrrolo[2,3‐b]quinoxaline Derivatives as Potential Cytotoxic Agents

Toward Greener Chemistry Methods for Preparation of Hybrid Polymer Materials Based on Carbon Nanotubes

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