KF/Al2O3 and PEG-400 as a recyclable medium for the selective α-selenation of aldehydes and ketones. Preparation of potential antimicrobial agents

Victoria, Francine Novack; Radatz, Cátia S.; Sachini, Maraísa; Jacob, Raquel G.; Perin, Gelson; Silva, Wladimir Padilha da; Lenardão, Eder J.

doi:10.1016/j.tetlet.2009.09.093

Cited by 52 publications

(8 citation statements)

References 24 publications

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“…All reagents and chemicals were commercially available and used as received. Alumina-supported potassium fluoride (KF/Al 2 O 3 ) was prepared by literature method [ 24 ]. The dihydrobenzothiazole derivatives 1 were prepared as reported method by us [ 19 , 20 ].…”

Section: Methodsmentioning

confidence: 99%

Antinociceptive properties of new coumarin derivatives bearing substituted 3,4-dihydro-2H-benzothiazines

et al. 2014

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BackgroundCoumarins are an important class of widely distributed heterocyclic natural products exhibiting a broad pharmacological profile. In this work, a new series of coumarins bearing substituted 3,4-dihydro-2H-benzothiazines were described as potential analgesic agents. The clinical use of NSAIDs as traditional analgesics is associated with side effects such as gastrointestinal lesions and nephrotoxicity. Therefore, the discovery of new safer drugs represents a challenging goal for such a research area.ResultsThe target compounds 3-(3-methyl-3,4-dihydro-2H-benzo[b][1,4]thiazin-3-yl)-2H-chromen-2-ones 2a-u were synthesized and characterized by spectral data. The antinociceptive properties of target compounds were determined by formalin-induced test and acetic acid-induced writhing test in mice. Among the tested compounds, compound 2u bearing 2-(4-(methylsulfonyl)benzoyl)- moiety on benzothiazine ring and 4-(methylsulfonyl)phenacyloxy- group on the 7 position of coumarin nucleus showed better profile of antinocecieption in both models. It was more effective than mefenamic acid during the late phase of formalin-induced test as well as in the acetic acid-induced writhing test.ConclusionConsidering the significant antinoceciptive action of phenacyloxycoumarin derivatives, compound 2u prototype might be further used as model to obtain new more potent analgesic drugs.

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Section: Methodsmentioning

confidence: 99%

Antinociceptive properties of new coumarin derivatives bearing substituted 3,4-dihydro-2H-benzothiazines

et al. 2014

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“…75,76 Estas substâncias apresentaram efeito antiplaquetário, o que indica um elevado potencial desta classe de compostos para o possível uso como agentes antitrombóticos. 49,54,57,61,65,77 Neste contexto, a metodologia de eneciclização do (R)-citronelal 1 (Esquema 2) foi aplicada diretamente no óleo essencial bruto de citronela (C. nardus), sem isolamento prévio do citronelal. 49 Quando o OE de citronela (contendo 45 % de (R)-citronelal 1) foi irradiado no micro-ondas (427 W) por 1 minuto, na presença de SiO 2 /ZnCl 2 (10 %), observou-se 10 0% de conversão ao (-)-isopulegol 2.…”

Section: Eugenolunclassified

Essential Oils as a Sustainable Raw Material for the Preparation of Products with Higher Value-Added

Jacob

2017

Rev. Virtual Quim.

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Abstract:The use of renewable feedstocks, which may substitute those derived from petroleum, is currently a great challenge in the chemical and pharmaceutical industries. However, plant essential oils (EOs) that have been studied for their biological activities, such as antioxidant, antimicrobial, antifungal and antinociceptive are generally regarded as safe additives maintaining the microbiological stability of foods. EOs are a mixture of natural volatile compounds, that are predominantly formed during the secondary metabolism in plants and commonly concentrated in the leaves, bark or fruits of aromatic plants. They are complex mixtures composed mainly of terpenes (hydrocarbons or oxygenated compounds) and phenylpropanoids, which can be used as a source of raw materials for fine chemicals industry. In recent years, researchers and industries have been focusing on the major compounds of EOs in order to use them as solvents or as bio-based building blocks adding value to this material derived from biomass.Keywords: Essential oil; bio-based compounds; biomass. ResumoO uso de matérias-primas renováveis, que podem substituir os derivados de petróleo, é atualmente um grande desafio para as indústrias químicas e farmacêuticas. No entanto, os óleos essenciais (OEs) de plantas que têm sido estudados pelas suas atividades biológicas, tais como antioxidante, antimicrobiana, antifúngica e antinociceptiva, são geralmente considerados como aditivos seguros para a manutenção da estabilidade microbiológica de alimentos. Os OEs são uma mistura de compostos voláteis naturais, que são formados durante o metabolismo secundário das plantas e geralmente concentrados nas folhas, casca ou frutos de plantas aromáticas. Eles são misturas complexas compostas principalmente de terpenos (hidrocarbonetos ou compostos oxigenados) e fenilpropanoides, que podem ser utilizados como uma fonte de matéria-prima para a indústria de química fina. Nos últimos anos, pesquisadores e indústrias estão focados nos componentes majoritários dos OEs, a fim de usá-los como solventes ou como blocos de construção de base biológica agregando valor a este material derivado de biomassa.

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“…The solid‐supported KF/Al 2 O 3 associated with PEG‐400 as the solvent was employed by us as a reusable catalytic system in the α‐selenylation of aldehydes and ketones to prepare functionalized selenoethers 191 and 192 respectively (Scheme ) . This clean synthetic protocol was successfully applied to aliphatic and cyclic ketones 26 giving the 2‐phenylseleno derivatives 192 in 67–96 % yields after few hours.…”

Section: Synthesis Of Chalcogen Ethersmentioning

confidence: 99%

Synthesis of Organochalcogen Compounds using Non-Conventional Reaction Media

et al. 2016

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This review is dedicated to the memory of Prof. Nicola Petragnani, a pionner in the chemistry of selenium and tellurium in Brazil, who passed away on December 5, 2015.Organochalcogen compounds (containing S, Se and Te) are interesting either for use as an intermediate in the synthesis of complex molecules or for the exploitation of their biological properties. The growing in the number of papers on the synthesis and application of organochalcogen compounds has been accompanied by a concern about how they are prepared. Here, we provide a comprehensive and updated review on re-cent synthetic methods available for their synthesis using alternative solvents or solvent-free conditions and non-classical energy sources (microwaves irradiation, sonochemistry and mechanochemistry). Organized in fourteen sections, this review brings the more than one hundred alternative methods described so far to access organic compounds containing selenium, tellurium and sulfur.[a] Prof.

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KF/Al2O3 and PEG-400 as a recyclable medium for the selective α-selenation of aldehydes and ketones. Preparation of potential antimicrobial agents

Cited by 52 publications

References 24 publications

Antinociceptive properties of new coumarin derivatives bearing substituted 3,4-dihydro-2H-benzothiazines

Antinociceptive properties of new coumarin derivatives bearing substituted 3,4-dihydro-2H-benzothiazines

Essential Oils as a Sustainable Raw Material for the Preparation of Products with Higher Value-Added

Synthesis of Organochalcogen Compounds using Non-Conventional Reaction Media

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