Síntese de teluroalquinos mediada por K3PO4 e DMSO

In the present work, a simple and efficient methodology is described by reactions between terminal alkynes 1a-m and diorganyl ditellurides 2a-e in the presence of potassium phosphate (K3PO4) and DMSO, in order to obtain different alkynyltellurides 3a-qAfter determination of the best reaction condition, this method was applied to different terminal alkynes 1a-m and diorganyl ditellurides 2a-e, using electron donating and withdrawing substituents. In both substrates, it was possible to vary the aryl and alkyl groups, obtaining the products of interest in short reaction times and in yields ranging from 30 to 93%. This methodology, differently from those already reported in literature, has the advantage of not using metallic catalysts, but only a weak base is used.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESNo presente trabalho, descreve-se uma metodologia simples e eficiente através de reações entre alquinos terminais 1a-m e diteluretos de diorganoíla 2a-e na presença de fosfato de potássio (K3PO4) e DMSO, para a obtenção de diferentes teluroalquinos 3a-qApós a determinação da melhor condição reacional, este método foi aplicado a diferentes alquinos terminais 1a-m e diteluretos de diorganoíla 2a-e, utilizando-se grupos doadores e retiradores de elétrons como substituintes. Em ambos os substratos, foi possível variar os grupos arila e alquila, obtendo os produtos de interesse em curtos tempos reacionais e com rendimentos que variaram de 30 a 93%. Esta metodologia tem como vantagem, frente as já descritas na literatura, não fazer o uso de catalisadores metálicos, uma vez que utiliza-se apenas uma base fraca

Correction: Computational and biological evidences on the serotonergic involvement of SeTACN antidepressant-like effect in mice.

[This corrects the article DOI: 10.1371/journal.pone.0187445.]

Selective Synthesis of 2-(1,2,3-Triazoyl) Quinazolinones through Copper-Catalyzed Multicomponent Reaction

We describe here our results from the copper-catalyzed three component reaction of 2-azidobenzaldehyde, anthranilamide and terminal alkynes, using Et3N as base, and DMSO as solvent. Depending on the temperature and amount of Et3N used in the reactions, 1,2,3-triazolyl-quinazolinones or 1,2,3-triazolyl-dihydroquinazolinone could be obtained. When the reactions were performed at 100 °C using 2 equivalents of Et3N, 1,2,3-triazolyl-dihydroquinazolinone was formed in 82% yield, whereas reactions carried out at 120 °C using 1 equivalent of Et3N provided 1,2,3-triazolyl-quinazolinones in moderate-to-good yields

Computational and biological evidences on the serotonergic involvement of SeTACN antidepressant-like effect in mice

<div><p>A series of phenylselanyl-1<i>H</i>-1,2,3-triazole-4-carbonitriles with different substituents were screened for their binding affinity with serotonin transporter (SERT) and dopamine transporter (DAT) by docking molecular. 5-(4methoxyphenyl)-1-(2-(phenylselanyl)phenyl)-1H-1,2,3-triazole-4-carbonitrile (SeTACN) exhibited the best conformation with SERT even higher than fluoxetine and serotonin, suggesting a competitive inhibition. SeTACN demonstrated additional affinity to other serotonergic receptors involved in antidepressant effects: 5HT_1a, 5HT_2a and 5HT₃. In another set of experiments, SeTACN led to significant reductions in the immobility time of mice submitted to forced swimming test (FST) in the dose range of 0.1- 20mg/kg, suggesting an antidepressant-like effect. The possible mechanism of action was investigated using serotonergic and dopaminergic antagonists. The antidepressant-like effect of SeTACN (0.1mg/kg i.g.) was prevented by the pretreatment with WAY100635 (a selective 5HT_1a antagonist), ketanserin (a 5HT2_a/c antagonist) and ondansetron (a selective 5ht₃ antagonist), PCPA (an inhibitor of serotonin synthesis) but not with SCH23390 (dopaminergic D₁ antagonist) and sulpiride (D₂ antagonist). Sub-effective dose of fluoxetine was able to potentiate the effects of a sub-effective dose of SeTACN in FST. None of the treatments affected locomotor activity in open field test (OFT). These results together, suggest that the SeTACN antidepressant-like effect is mediate, at least in parts, by serotonergic system.</p></div

Scores (kcal/mol) of docking results of phenylselanyl-1<i>H</i>-1,2,3-triazole-4-carbonitriles class of compounds in serotonin transporter (SERT) and dopamine transporter (DAT).

<p>Scores (kcal/mol) of docking results of phenylselanyl-1<i>H</i>-1,2,3-triazole-4-carbonitriles class of compounds in serotonin transporter (SERT) and dopamine transporter (DAT).</p

Computational and biological evidences on the serotonergic involvement of SeTACN antidepressant-like effect in mice - Fig 6

<p>Effect of pretreatment of mice with (A) SCH233390 (0.05 mg/kg, s.c., a dopaminergic D₁ receptor antagonist) and (B) sulpiride (50 mg/kg, i.p., a dopaminergic D₂ receptor antagonist) on the anti-immobility effect of SeTACN (0.1mg/kg, i.g) in the FST. Data are presented as the mean ± S.E.M. (***) P < 0.001 in comparison to the vehicle treated group.</p

Experimental paradigms illustrating the drugs and compound administration followed by behavioral tests.

<p>(A) Antidepressant-like activity of 5-(4methoxyphenyl)-1-(2-(phenylselanyl)phenyl)-1H-1,2,3-triazole-4-carbonitrile (SeTACN). (B) Evaluation of mechanism of action involved in antidepressant-like effect of SeTACN. (C) Synergic effect of the combined treatment with sub-effective doses of clinical antidepressants and SeTACN.</p

Chemical structure of class phenylselanyl-1<i>H</i>-1,2,3-triazole-4-carbonitriles compounds.

<p>Compound 1: 5-phenyl-1-(2-(phenylselanyl)phenyl)-1H-1,2,3-triazole-4-carbonitrile; Compound 2: 5-(4-fluorophenyl)-1-(2-(phenylselanyl)phenyl)-1H- 1,2,3-triazole-4-carbonitrile; Compound 3: 5-(4-chlorophenyl)-1-(2-(phenylselanyl)phenyl)-1H- 1,2,3-triazole-4-carbonitrile; Compound 4: 5-(4-methoxyphenyl)-1-(2-(phenylselanyl)phenyl)-1H- 1,2,3-triazole-4-carbonitrile and Compound 5: 1-(2-(phenylselanyl)phenyl)-5-(p-tolyl)-1H-1,2,3- triazole-4-carbonitrile.</p