Vibrational spectroscopic study of some quinoline derivatives

Fernandes, Rafaella F.; Stroppa, Pedro Henrique Fazza; Ferreira, Gilson R.; Silva, Adilson David da; Edwards, Howell G. M.; Oliveira, Luiz Fernando Cappa de

doi:10.1016/j.vibspec.2016.06.005

Cited by 15 publications

(8 citation statements)

References 32 publications

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“…Further, the IR-active modes confirm that co-crystals were obtained with a monoclinic-like structure. These results are consistent with experimental observations for both (hydroxy)chloroquine and macrolide antibiotics [1,12,42,43]. As can be seen in Figure 3, the computed UV-vis absorption spectrum of these co-crystals revealed only one well-defined peak.…”

Section: Resultssupporting

confidence: 91%

New In Silico Insights into the Application of (Hydroxy)Chloroquine with Macrolide Antibiotic Co-Crystals against the SARS-CoV-2 Virus

Castro

Assis

Cunha

et al. 2022

COVID

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In this in silico study, different pharmaceutical co-crystals based on (hydroxy)chloroquine with macrolide antibiotics (azithromycin, clarithromycin, or erythromycin A) were analyzed for the first time. These findings present a new molecular perspective and therefore suggest that the combination of (hydroxy)chloroquine/azithromycin, in the stoichiometric ratio of 1:1, as model co-crystal systems has less toxicity and is the most effective for inhibiting the new severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2).

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Section: Resultssupporting

confidence: 91%

New In Silico Insights into the Application of (Hydroxy)Chloroquine with Macrolide Antibiotic Co-Crystals against the SARS-CoV-2 Virus

Castro

Assis

Cunha

et al. 2022

COVID

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“…The IR spectrum of 3 is illustrated in Figures S2 and S3. The ester group possesses two asymmetrically coupled vibrations, namely C-C(=O)-O and O-C-C, which appear in the region of 1250-1310 cm −1 and 1111 cm −1 , respectively [49,50]. For compound 3, we observed C-C(=O)-O and O-C-C stretching vibrations at 1258 and 1087 cm −1 , respectively.…”

Section: Vibrational Analysismentioning

confidence: 74%

Crystal Structure, Hirshfeld Surface Analysis, and Computational Study of Quinolin-8-yl 4-Chlorobenzoate: Insights from Spectroscopic, Thermal, and Antitumor Properties

2023

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We report the time-efficient synthesis of quinolin-8-yl 4-chlorobenzoate (3) via an O-acylation reaction between 8-hydroxyquinoline (1) and 4-chlorobenzoyl chloride (2) mediated by triethylamine in acetonitrile under heating at 80 °C for 20 min in the Monowave 50 reactor. This protocol is distinguished by its short reaction time, operational simplicity, and clean reaction profile. The structure of 3 was fully characterized through a combination of analytical techniques, including NMR, IR, and UV–Vis spectroscopy, MS spectrometry, differential scanning calorimetry (DSC), thermogravimetry (TG), and crystallographic studies. Interestingly, X-ray diffraction analyses of 3 show that the crystal structure is characterized by C-H···N, C-H···O, Cl···π, and π···π interactions. The molecular conformation presents an orthogonal orientation between aromatic rings in the solid state. The calculated interaction energies using the CE-B3LYP model show that dispersion forces act in a higher proportion to build the crystal, which is consistent with the few short hydrogen interactions detected. Electrostatic potential maps suggest the formation of σ-holes over the Cl atoms. Although they can behave as both Lewis acid and base sites, Cl··Cl interactions are absent due to the shallow depth of these σ-holes. Quantum chemical descriptors and global reactivity descriptors were examined using the B3LYP method with the 6-31G(d,p) basis set implemented in CrystalExplorer. Finally, compound 3 exhibited low activity against HOP-92 and EKVX non-Small-cell lung and UO-31 Renal cancer cell lines, with a growth inhibition percentage (GI%) ranging from 6.2% to 18.1%.

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“…The peaks at 1057, 1133, and 1314 cm –1 are attributed to CH bending. The peak at 1264 cm –1 represents CNC bending, and the peak at 1463 can be assigned to CH rocking. − The quinoline peak assignments are summarized in the Supporting Information (Table S2). Two non-quinoline peaks at 1002 and 1145 cm –1 found in the experimental spectra could be contributed to the residual of methanol used to clean the microscope objective lens as their peak intensity did not increase with the increase of quinoline concentration.…”

Section: Resultsmentioning

confidence: 99%

“…CCC stretching modes contribute to the peaks at 1372, 1392, and 1571 cm –1 . CH rocking modes give rise to the peak at 1433 cm –1 . − Two peaks at 760 and 1372 cm –1 are the most intense among all peaks. For quinoline quantification, the Raman peak at 770 cm –1 (a shift from 760 cm –1 ) was first used for signal quantification.…”

Section: Materials and Methodsmentioning

confidence: 99%

Sensing Antibiotics in Wastewater Using Surface-Enhanced Raman Scattering

Huang

Hong

Santiago

et al. 2023

Environ. Sci. Technol.

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Rapid and cost-effective detection of antibiotics in wastewater and through wastewater treatment processes is an important first step in developing effective strategies for their removal. Surface-enhanced Raman scattering (SERS) has the potential for label-free, real-time sensing of antibiotic contamination in the environment. This study reports the testing of two gold nanostructures as SERS substrates for the label-free detection of quinoline, a small-molecular-weight antibiotic that is commonly found in wastewater. The results showed that the self-assembled SERS substrate was able to quantify quinoline spiked in wastewater with a lower limit of detection (LoD) of 5.01 ppb. The SERStrate (commercially available SERS substrate with gold nanopillars) had a similar sensitivity for quinoline quantification in pure water (LoD of 1.15 ppb) but did not perform well for quinoline quantification in wastewater (LoD of 97.5 ppm) due to interferences from non-target molecules in the wastewater. Models constructed based on machine learning algorithms could improve the separation and identification of quinoline Raman spectra from those of interference molecules to some degree, but the selectivity of SERS intensification was more critical to achieve the identification and quantification of the target analyte. The results of this study are a proof-of-concept for SERS applications in label-free sensing of environmental contaminants. Further research is warranted to transform the concept into a practical technology for environmental monitoring.

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Vibrational spectroscopic study of some quinoline derivatives

Cited by 15 publications

References 32 publications

New In Silico Insights into the Application of (Hydroxy)Chloroquine with Macrolide Antibiotic Co-Crystals against the SARS-CoV-2 Virus

New In Silico Insights into the Application of (Hydroxy)Chloroquine with Macrolide Antibiotic Co-Crystals against the SARS-CoV-2 Virus

Crystal Structure, Hirshfeld Surface Analysis, and Computational Study of Quinolin-8-yl 4-Chlorobenzoate: Insights from Spectroscopic, Thermal, and Antitumor Properties

Sensing Antibiotics in Wastewater Using Surface-Enhanced Raman Scattering

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