An interdisciplinary study on monosubstituted benzene involving computation, statistics and chemistry

Ferreira, João Elias Vidueira; Costa, Clauber Henrique Souza da; Miranda, Ricardo Morais de; Figueiredo, Antonio Florêncio de; Ginarte, Yoanna María Álvarez

doi:10.1016/s0187-893x(14)70061-8

Cited by 5 publications

(4 citation statements)

References 5 publications

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“…Subsequently, it was decided to introduce electron donating groups (EDG) and electron withdrawing groups (EWG) in the aromatic ring to observe its effect on the biological activity. Although all substitutions improved activity with respect to derivative 2b, the trend shows that substitutions with strong EDG and EWG 28 (3d and 3j) generate worse results with respect to derivatives that have weak EDG and EWG 29,30 (3f, 3h and 3i). This effect is due to the greater lipophilic capacity of these derivatives (3f = 8.14; 3h = 8.04 and 3i = 8.37) ( Table 3).…”

Section: Resultsmentioning

confidence: 96%

Synthesis and biological screening of a library of macamides as TNF-α inhibitors

et al. 2020

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Section: Resultsmentioning

confidence: 96%

Synthesis and biological screening of a library of macamides as TNF-α inhibitors

et al. 2020

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“…PCA and HCA are pattern recognition methods that generate potent visualization tools (dendrogram for HCA and score plots for PCA). In this study, HCA was used for classifying pineapple samples into its varieties and PCA was used primarily to find principal components which describe each variable [27]. PCA analyses were performed on the same data sets to determine which parameter explains how each sample was different from one another [28].…”

Section: Resultsmentioning

confidence: 99%

Combining Chemometrics, Sensory Analysis and Chromatographic Fingerprint of Volatile, and Phenolic Compositions for Systematic Classification of Pineapple (Ananas comosus L.)

2021

MJCHEM

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Classification and quality control of fruits in Malaysia is based on the morphological traits manual carried out by the agricultural officer. As this approach is based on human perception and judgment, it may be biased and inconsistent. The aroma of pineapple is made up of a wide range of volatile and non-volatile compounds depending on the varieties and maturity stages of the fruits and thus, can be valuable factors in classifying the fruits. The chromatographic fingerprints of volatile and phenolic compounds from pineapple pulp were obtained by using Gas Chromatography-Mass Spectrometry Detector (GC-MSD) and 2-Dimensional-Liquid Chromatography -Diode Array Detector (2D-LC-DAD), respectively. Sensory profiles, conducted using quantitative descriptive analysis (QDA), showed that the fruity aroma of pineapple were not able to differentiate between the pineapple varieties with scales of 4.13±2.07, 5.33±2.58, 3.87±2.07, and 3.00±0.00 for the Morris, Josephine, MD2, and Sarawak varieties, respectively. Thus, sensory analysis alone could be biased and unreliable in discriminating pineapple varieties. Chemometric techniques based on unsupervised (principal component analysis (PCA) and hierarchical cluster analysis (HCA)), and supervised (discriminant analysis (DA) and partial least squares discriminant analysis (PLS-DA) using 13 sensory attributes, 10 selected phenolic compounds, and 35 volatile compounds allowed the discrimination of these four pineapple varieties.

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“…Based on these results, we decided to analyse how the introduction of a methyl group (electron donating groups, EDG) [42][43] in the ortho (11), meta (12) and para (13) positions in the aromatic ring of the analogue 7 influences the pharmacological activity. Our results show that the substitutions in the meta (analogue 12) and para (analogue 13) positions with the methyl group led to a slight decrease in cell viability, showing CC 50 values between 86.23-87.73 μM and 87.8-88.97 μM, respectively ( not significant statistically when compared to analogue 7, ns p > 0.999) ( Table 1).…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Pharmacological Evaluation of N‐Benzyl Linoleamide Analogues from Tropaeolum tuberosum as NF‐κB Inhibitors and Nrf2 Activators

et al. 2020

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Nineteen N-benzyl linoleamide analogues (macamide from Tropaeolum tuberosum) were synthesised, modifying the molecular structure (benzyl position, aromatic ring and carbonyl group). The structures were confirmed using nuclear magnetic resonance and mass spectrometry techniques. Cell viability and anti-inflammatory activity of these compounds were evaluated in three brain cell lines (C8-D1 A, Neuro-2a, and EOC 13.31). Regarding the effect on NF-kB, several analogues had better inhibition potential than their natural precursor (N-benzyl linoleamide), being the N-(1-(3,5-dimethyl-α-methylbenzyl)-linolethiamide the most active, with IC 50 values of 0.01 � 0.01, 0.01 � 0.01 and 0.02 � 0.01 μM, respectively. Finally, all analogues activated Nrf2, with the same compound being the most active, presenting EC 50 values of 0.03 � 0.01, 0.07 � 0.01 and 0.11 � 0.02 nM, respectively. Analysing the link between chemical structure and pharmacological activity, our study shows that the changes made to N-benzyl linoleamide lead us to obtaining an analogue with greater anti-inflammatory activity than its precursor and with potential for the treatment of migraine.

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An interdisciplinary study on monosubstituted benzene involving computation, statistics and chemistry

Cited by 5 publications

References 5 publications

Synthesis and biological screening of a library of macamides as TNF-α inhibitors

Synthesis and biological screening of a library of macamides as TNF-α inhibitors

Combining Chemometrics, Sensory Analysis and Chromatographic Fingerprint of Volatile, and Phenolic Compositions for Systematic Classification of Pineapple (Ananas comosus L.)

Design, Synthesis and Pharmacological Evaluation of N‐Benzyl Linoleamide Analogues from Tropaeolum tuberosum as NF‐κB Inhibitors and Nrf2 Activators

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