Synthesis of beta-phenylchalcogeno-alpha, beta-unsaturated esters, ketones and nitriles using microwave and solvent-free conditions

Lenardão, Eder J.; Silva, Márcio S.; Mendes, Samuel R.; Jacob, Raquel G.; Santos, Paulo César S.; Perin, Gelson

doi:10.1590/s0103-50532007000500011

Cited by 25 publications

(8 citation statements)

References 28 publications

(39 reference statements)

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“…Consequently, occupational exposure is a constant risk for laboratory workers (Petragnani, 1994;Comasseto et al, 1997;Zeni et al, 2003Zeni et al, , 2006. The organotellurium 3-butyl-1-phenyl-2-(phenyltelluro)oct-en-1-one is an a,bunsaturated ketone functionalized vinyl chalcogenide that has been found to be a potential tool in organic synthesis (Lenardão et al, 2007;Penz et al, 2009;Carvalho et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

Inhibition of creatine kinase activity by 3‐butyl‐1‐phenyl‐2‐(phenyltelluro)oct‐en‐1‐one in the cerebral cortex and cerebellum of young rats

Andrade

Gemelli

Guerra

et al. 2010

J of Applied Toxicology

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In the present study, we investigated the potential in vitro toxicity of the tellurium compound 3-butyl-1-phenyl-2-(phenyltelluro)oct-en-1-one on creatine kinase activity in cerebral cortex and cerebellum of 30-day-old Wistar rats. First, enriched mitochondrial and cytosolic fractions from the two tissues were pre-incubated for 30 min in the presence or absence of 1, 5 or 20 microm of organotellurium and the creatine kinase activity was measured. The organochalcogen reduced creatine kinase activity in a concentration-dependent pattern in the two tissues studied. Furthermore, the enzyme activity was performed after pre-incubation for 30, 60 or 90 min in the presence of 5 microm of the organotellurium. The compound inhibited creatine kinase activity in a time-dependent way in the enriched mitochondrial fraction of both tissues, but not in the cytosolic fraction, indicating different mechanisms for the organochalcogen in the mitochondrial and in the cytosolic creatine kinase. Pre-incubation of tellurium compound with reduced glutathione suggests that creatine kinase activity inhibition might be caused by direct interaction with thiol groups or by oxidative stress. Our findings suggest that creatine kinase inhibition may be one of the mechanisms by which this organotellurium could cause toxicity to the rat brain.

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Section: Introductionmentioning

confidence: 99%

Inhibition of creatine kinase activity by 3‐butyl‐1‐phenyl‐2‐(phenyltelluro)oct‐en‐1‐one in the cerebral cortex and cerebellum of young rats

Andrade

Gemelli

Guerra

et al. 2010

J of Applied Toxicology

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“…The solvent‐free hydrochalcogenation of alkynes 41 promoted by NaBH 4 /Al 2 O 3 was extended to several other Michael acceptor alkynes 41 (esters, ketones and nitrile) and diphenyl disulfides 4 c , diselenides 1 a and ditellurides 38 a (Scheme ) . Diphenyl ditellurides gave better selectivity ( Z:E ratio=83:17‐100:0), while diphenyl disulfide was not effective in the hydrothiolation reaction; in this case, the commercially available sodium phenylthiolate was used as the sulfur source.…”

Section: Synthesis Of Vinyl Chalcogenidesmentioning

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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“…Vinylic compounds are important synthetic intermediates because of their easy transformation into other organic compounds with retention of configuration. 14,15 Several lines of investigations on the cellular metabolism of purines in peripheral tissues have generated considerable interest in adenosine deaminase (ADA; E.C. 3.5.4.4), an enzyme involved in purine metabolism that catalyzes the hydrolytic deamination of adenosine or 2 0 -deoxyadenosine to inosine or 2 0 -deoxyinosine.…”

Section: Introductionmentioning

confidence: 99%

“…Vinylic compounds are important synthetic intermediates because of their easy transformation into other organic compounds with retention of configuration. 14,15…”

Section: Introductionmentioning

confidence: 99%

Differential effects of organic and inorganic selenium compounds on adenosine deaminase activity and scavenger capacity in cerebral cortex slices of young rats

et al. 2013

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Selenium (Se) has anti-inflammatory and antioxidant properties and is necessary for the development and normal function of the central nervous system. This study was aimed to compare the in vitro effects of 3-methyl-1-phenyl-2-(phenylseleno)oct-2-en-1-one (C21H2HOSe; organoselenium) and sodium selenate (inorganic Se) on adenosine deaminase (ADA) activity, cell viability, lipid peroxidation, scavenger of nitric oxide (NO) and nonprotein thiols (NP-SH) content in the cerebral cortex slices of the young rats. A decrease in ADA activity was observed when the slices were exposed to organoselenium at the concentrations of 1, 10 and 30 µM. The same compound showed higher scavenger capacity of NO than the inorganic compound. Inorganic Se was able to protect against sodium nitroprusside-induced oxidative damage and increased the NP-SH content. Both the compounds displayed distinctive antioxidant capacities and were not cytotoxic for the cerebral cortex slices in the conditions tested. These findings are likely to be related to immunomodulatory and antioxidant properties of this compound.

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Synthesis of beta-phenylchalcogeno-alpha, beta-unsaturated esters, ketones and nitriles using microwave and solvent-free conditions

Abstract: a,b-unsaturated esters, ketones and nitriles, in good yield and higher selectivity, compared with those that use organic solvent and inert atmosphere. The use of microwave (MW) irradiation facilitates the procedure and accelerates the reaction.]]>

Cited by 25 publications

References 28 publications

Inhibition of creatine kinase activity by 3‐butyl‐1‐phenyl‐2‐(phenyltelluro)oct‐en‐1‐one in the cerebral cortex and cerebellum of young rats

Inhibition of creatine kinase activity by 3‐butyl‐1‐phenyl‐2‐(phenyltelluro)oct‐en‐1‐one in the cerebral cortex and cerebellum of young rats

Synthesis of Organochalcogen Compounds using Non-Conventional Reaction Media

Differential effects of organic and inorganic selenium compounds on adenosine deaminase activity and scavenger capacity in cerebral cortex slices of young rats

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