Intramolecular 4π photocyclization of chalconoid-like compounds in solution and antimicrobial activities

Yaylı, Nurettin; Sivrikaya, Serpil Ö.; Yaşar, Ahmet; Üçüncü, Osman; Güleç, Canan; Kolaylı, Sevgi; Küçük, Murat; Çelik, Elif

doi:10.1016/j.jphotochem.2005.03.025

Cited by 11 publications

(12 citation statements)

References 25 publications

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“…Figure 1 shows the natural antioxidants which posses the chalcone backbone. Some of the synthetic chalcones which have hydroxyl and methoxy substitutions also are found to posses antioxidant activity (Yayli et al, 2005). Previous researchers also found that o-, m-, and p-nitro substituted azachalcones are also potential antioxidant agents (Yayli et al, 2006).…”

Section: Superoxide (Omentioning

confidence: 98%

Synthesis, antioxidant evaluation, and quantitative structure–activity relationship studies of chalcones

2010

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Synthesis, antioxidant activity, and quantitative structure-activity relationship (QSAR) of 25 of chalcone derivatives is reported here. They were synthesized by Claisen-Schmidt reaction and were characterized by FTIR, NMR, and mass spectroscopy. Antioxidant activity is evaluated through four different methods namely, superoxide radical-scavenging, hydrogen peroxide scavenging, reducing power, and DPPH radical-scavenging assays. Generally, compounds with -SCH 3 and -OCH 3 in the para position of the A-ring and -OH in the B-ring were more active than others. In few cases some of the compounds were more active than ascorbic acid or butylated hydroxytoluene. QSAR was developed correlating the antioxidant activity with the structural features of the compounds and the predictive capability of the models was estimated using internal and external validation methods. All the predictions were within the 99% confidence level. Spatial, structural, and lipophilic properties of the compounds determine their antioxidant properties.

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Section: Superoxide (Omentioning

confidence: 98%

Synthesis, antioxidant evaluation, and quantitative structure–activity relationship studies of chalcones

2010

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“…The alternative mechanism, illustrated in Scheme , depends on charge location at the nitro group ( 19 ). In pathway a, the elimination of H 2 O occurs through formation of a triple bond as a consequence of a ‐hydrogen shift leading to the formation of 23 . Another mechanism can be rationalized by considering a ‐hydrogen shift of the acidic hydrogen neighbour to the nitro group ( 25 , pathway b).…”

Section: Resultsmentioning

confidence: 99%

“…The antimicrobial activity of several ortho ‐, meta ‐ and para ‐NO 2 , OCH 3 and CH 3 ring A‐substituted cinnamylideneacetophenones was investigated more recently . All these compounds showed antimicrobial activity against Gram‐positive and Gram‐negative bacteria, but no antifungal activity was observed against yeast‐like fungi.…”

Section: Methodsmentioning

confidence: 99%

“…All these compounds showed antimicrobial activity against Gram‐positive and Gram‐negative bacteria, but no antifungal activity was observed against yeast‐like fungi. Of this series, the ortho ‐nitro‐substituted compound showed the most promising results (namely 60 µg/mL minimum inhibitory concentration against S. aureus , B. cereus and E. faecalis ) . Cinnamylideneacetophenones bearing ortho ‐OH and para ‐OCH 3 substituents on ring A were also screened for their potential use as hypolipidemic agents .…”

Section: Methodsmentioning

confidence: 99%

“…[4] The antimicrobial activity of several ortho-, meta-and para-NO 2 , OCH 3 and CH 3 ring A-substituted cinnamylideneacetophenones was investigated more recently. [5] All these compounds showed antimicrobial activity against Gram-positive and Gram-negative bacteria, but no antifungal activity was observed against yeastlike fungi. Of this series, the ortho-nitro-substituted compound showed the most promising results (namely 60 mg/mL minimum inhibitory concentration against S. aureus, B. cereus and E. faecalis).…”

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confidence: 99%

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Tandem mass spectrometry based investigation of cinnamylideneacetophenone derivatives: valuable tool for the differentiation of positional isomers

Resende

Silva

Barros

et al. 2011

Rapid Comm Mass Spectrometry

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Cinnamylideneacetophenones have been extensively used as versatile starting materials in numerous different transformations. The structural characterization of this type of compounds is, therefore, of crucial importance since it can give information on the chemistry, reactivity and also the potential biological activity of this type of compounds. Thus, 24 derivatives were systematically studied by tandem mass spectrometry (MS(2)) with electrospray ionization (ESI), in positive ion mode. The protonated molecules, [M + H](+), formed under ESI conditions were induced to dissociate and the fragmentation patterns were studied. The information collected provided important structural information on the type of substituents present and constitute an important database concerning this family of compounds. Overall, it was found that the substitution pattern of the cinnamylideneacetophenone derivatives changes the ESI-MS(2) fragmentation considerably. These results indicate that ESI-MS(2) is a useful technique for distinguishing positional isomers of these cinnamylideneacetophenone derivatives.

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Do cinnamylideneacetophenones have antioxidant properties and a protective effect toward the oxidation of phosphatidylcholines?

Silva

Melo

Sousa

et al. 2016

European Journal of Medicinal Chemistry

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Intramolecular 4π photocyclization of chalconoid-like compounds in solution and antimicrobial activities

Cited by 11 publications

References 25 publications

Synthesis, antioxidant evaluation, and quantitative structure–activity relationship studies of chalcones

Synthesis, antioxidant evaluation, and quantitative structure–activity relationship studies of chalcones

Tandem mass spectrometry based investigation of cinnamylideneacetophenone derivatives: valuable tool for the differentiation of positional isomers

Do cinnamylideneacetophenones have antioxidant properties and a protective effect toward the oxidation of phosphatidylcholines?

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