Synthesis, structural characterization and chromatic features of new 2-phenyl-1-benzopyrylium and 2-phenyl-styryl-1-benzopyrylium amino-based blue dyes

Araújo, Paula; Pereira, Ana Rita; Freitas, Víctor de; Mateus, Nuno; Fernandes, Iva

doi:10.1016/j.tetlet.2021.153487

Cited by 6 publications

(12 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…5,7OH 2 st4′NMe 2 was obtained from the condensation between 2,4,6-trihydroxybenzaldehyde (1.3 × 10 –4 mol, 20 mg) and p -dimethylaminostyrylmethylketone (1.6 × 10 –4 mol, 30 mg) in 259 μL (2 mL/1 mmol) of acetic acid and in the presence of hexafluorphosphoric acid (0.5 mL/1 mmol), as previously reported 13 . The mixture was left to react at room temperature during 24 h under stirring.…”

Section: Methodsmentioning

confidence: 98%

“…7NEt 2 4′NMe 2 was synthesized by acidic aldol, condensation between 4-diethylaminosalicylaldehyde and 4′-dimethylaminoacetophenone 13 . 4-diethylaminosalicylaldehyde (1.3 × 10 –3 mol, 250 mg) and 4′-dimethylaminoacetophenone (2.5 × 10 –3 mol, 410 mg) were weighted in a round bottom flask and dissolved in 12.5 mL of a mixture of ethyl acetate: methanol (2:1).…”

Section: Methodsmentioning

confidence: 99%

“…7NEt 2 st4′NMe 2 was synthesized from the reaction between 4-diethylaminosalicylaldehyde (1.0 × 10 –3 mol, 200 mg) and 4′-dimethylaminoacetophenone (1.0 × 10 –3 mol, 200 mg) in 2 mL of acetic acid as reported elsewhere 13 . Chlorotrimethylsilane (TMSCl; 20 equiv) was added and the mixture was left to react overnight at room temperature under stirring.…”

Section: Methodsmentioning

confidence: 99%

“…7NEt 2 4′NH 2 was synthesized by condensation between 4-diethylaminosalicylaldehyde (5.1 × 10 –4 mol, 100 mg) and 4′-aminoacetophenone (1.0 × 10 –3 mol, 140 mg) in 5 mL of a mixture of ethyl acetate: methanol (2:1) in the presence of chlorotrimethylsilane (TMSCl; 20 equiv) at room temperature during 4 h under stirring 13 .…”

Section: Methodsmentioning

confidence: 99%

“…Based on the knowledge about the current PS, it is possible to optimize the native structures of anthocyanins (absorption in the visible range from 450–530 nm) to yield proper candidates for PDT. For instance, the absorption properties of amino substituents on the 2-phenylbenzopyrylium cores (550–700 nm) may confer them one of the necessary features to be applied in this type of therapy 13 . Also, their photochromic properties were already described 14 .…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Photoactivated cell-killing amino-based flavylium compounds

Oliveira

Araújo

Pereira

et al. 2021

Sci Rep

Self Cite

View full text Add to dashboard Cite

Photodynamic therapy (PDT) is a well-established therapeutic for the treatment of different diseases. The growing interest of this technique required the development of new photosensitizers with better photo-features. This work reports the study of the potential of five nature-inspired amino-based flavylium compounds with different structural features as photosensitizers towards topical PDT. In terms of dark cytotoxicity the five pigments were tested towards confluent skin cells in both fibroblasts and keratinocytes. In the range of concentrations tested (6.3–100 μM), keratinocytes were more prone to growth inhibition and the IC50 values for 5OH4′NMe2, 7NEt2st4′NMe2 and 7NEt24′NH2 were determined to be 47.3 ± 0.3 μM; 91.0 ± 0.8 μM and 29.8 ± 0.8 μM, respectively. 7NEt24′NMe2, 7NEt2st4′NMe2 and 7NEt24′NH2 showed significant fluorescence quantum yields (from 3.40 to 20.20%) and production of singlet oxygen (1O2). These latter chromophores presented IC50 values of growth inhibition of keratinocytes between 0.9 and 1.5 µM, after 10 min of photoactivation with white light. This cellular damage in keratinocyte cells upon white light activation was accompanied with the production of reactive oxygen species (ROS). It was also found that the compounds can induce damage by either type I (ROS production) or type II (singlet oxygen) PDT mechanism, although a higher cell survival was observed in the presence of 1O2 quenchers. Overall, a structure–activity relationship could be established, ranking the most important functional groups for the photoactivation efficiency as follows: C7-diethylamino > C4′-dimethylamino > C2-styryl.

show abstract

Section: Methodsmentioning

confidence: 98%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Photoactivated cell-killing amino-based flavylium compounds

Oliveira

Araújo

Pereira

et al. 2021

Sci Rep

Self Cite

View full text Add to dashboard Cite

show abstract

Synthesis and pyrolysis of methyl cyclopentenolone succinate diester

Pan

Lai

et al. 2023

Flavour & Fragrance J

View full text Add to dashboard Cite

To develop a new class of enol diketone esters, succinic acid monoesters were synthesized using the reaction of succinic anhydride with various aromatic alcohols. Subsequently, six types of methyl cyclopentenolone succinate diesters were synthesized using dicyclohexylcarbodiimide (DCC) as the condensation agent and 4‐dimethylaminopyridine (DMAP) as the catalyst for the condensation reaction with methyl cyclopentenolone. The target compounds were characterized by nuclear magnetic resonance (1H NMR, 13C NMR), infrared spectroscopy (IR) and high‐resolution mass spectrometry (HRMS). The aromas characteristics of esters were evaluated using gas chromatography–mass spectrometry‐olfactometer (GC–MS‐O). Compounds 5a ~ 5c, which had a strong aroma, were conducted with thermogravimetry‐derivative thermogravimetry (TG‐DTG) to analyse their heating‐stability. Additionally, these compounds were studied by pyrolysis‐gas chromatography/mass spectrometry (Py‐GC/MS) to analyse their pyrolysis behaviours at 300, 350 and 400°C. Results showed that methyl cyclopentenolone and a large number of small molecular flavouring substances were formed by 5a ~ 5c at the set temperature. The synthesis of methyl cyclopentenolone succinate diester can not only slow down the volatilization of methyl cyclopentenolone and aromatic alcohol, but also effectively enhance the aroma, improve the smoking taste of cigarettes, reduce the irritation and miscellaneous gas of smoking and provide more choices for cigarette flavouring.

show abstract