دورية أكاديمية

Alkylated Sesamol Derivatives as Potent Antioxidants.

التفاصيل البيبلوغرافية
العنوان: Alkylated Sesamol Derivatives as Potent Antioxidants.
المؤلفون: C Palheta I; Núcleo de Estudos e Seleção de Moléculas Bioativas, Instituto de Ciências da Saúde, Universidade Federal do Pará, Belém 66075-110, Brazil., R Ferreira L; Núcleo de Estudos e Seleção de Moléculas Bioativas, Instituto de Ciências da Saúde, Universidade Federal do Pará, Belém 66075-110, Brazil.; Programa de Pós-Graduação em Química Medicinal e Modelagem Molecular, Instituto de Ciências da Saúde, Universidade Federal do Pará, Belém 66075-110, Brazil., K L Vale J; Núcleo de Estudos e Seleção de Moléculas Bioativas, Instituto de Ciências da Saúde, Universidade Federal do Pará, Belém 66075-110, Brazil., P P Silva O; Núcleo de Estudos e Seleção de Moléculas Bioativas, Instituto de Ciências da Saúde, Universidade Federal do Pará, Belém 66075-110, Brazil., M Herculano A; Programa de Pós-Graduação em Química Medicinal e Modelagem Molecular, Instituto de Ciências da Saúde, Universidade Federal do Pará, Belém 66075-110, Brazil., R H M Oliveira K; Programa de Pós-Graduação em Química Medicinal e Modelagem Molecular, Instituto de Ciências da Saúde, Universidade Federal do Pará, Belém 66075-110, Brazil., Neto AMJC; Faculdade de Física, Instituto de Ciências Exatas e Naturais, Universidade Federal do Pará, Belém 66075-110, Brazil., M Campos J; Department of Pharmaceutical Organic Chemistry, University of Granada, 18071 Granada, Spain., B R Santos C; Programa de Pós-Graduação em Química Medicinal e Modelagem Molecular, Instituto de Ciências da Saúde, Universidade Federal do Pará, Belém 66075-110, Brazil.; Laboratorio de Modelagem e Química Computacional-LMQC, Federal University of Amapá. Rod. Juscelino Kubitschek, Km 02, Macapá 68902-280, Brazil., S Borges R; Núcleo de Estudos e Seleção de Moléculas Bioativas, Instituto de Ciências da Saúde, Universidade Federal do Pará, Belém 66075-110, Brazil.; Programa de Pós-Graduação em Química Medicinal e Modelagem Molecular, Instituto de Ciências da Saúde, Universidade Federal do Pará, Belém 66075-110, Brazil.
المصدر: Molecules (Basel, Switzerland) [Molecules] 2020 Jul 21; Vol. 25 (14). Date of Electronic Publication: 2020 Jul 21.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: MDPI Country of Publication: Switzerland NLM ID: 100964009 Publication Model: Electronic Cited Medium: Internet ISSN: 1420-3049 (Electronic) Linking ISSN: 14203049 NLM ISO Abbreviation: Molecules Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Basel, Switzerland : MDPI, c1995-
مواضيع طبية MeSH: Antioxidants/*chemical synthesis , Benzodioxoles/*chemical synthesis , Phenols/*chemical synthesis, Alkylation ; Benzodioxoles/chemistry ; Butylated Hydroxyanisole/chemistry ; Butylated Hydroxytoluene/chemistry ; Chromans/chemistry ; Electron Transport ; Free Radicals/chemistry ; Molecular Structure ; Phenols/chemistry
مستخلص: Sesamol is a phenolic derivative. Its antioxidant activity is low than that of Trolox and depends on benzodioxole moiety. Thus, a molecular modification strategy through alkylation, inspired by natural and synthetic antioxidants, was studied by molecular modeling at the DFT/B3LYP level of theory by comparing the 6-31+G(d,p) and 6-311++G(2d,2p) basis sets. All proposed derivatives were compared to classical related antioxidants such as Trolox, t -butylated hydroxytoluene (BHT) and t -butylated hydroxyanisole (BHA). According to our results, molecular orbitals, single electron or hydrogen-atom transfers, spin density distributions, and alkyl substitutions at the ortho positions related to phenol moiety were found to be more effective than any other positions. The trimethylated derivative was more potent than Trolox. t -Butylated derivatives were stronger than all other alkylated derivatives and may be new alternative forms of modified antioxidants from natural products with applications in the chemical, pharmaceutical, and food industries.
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فهرسة مساهمة: Keywords: DFT; antioxidant capacity; electron transfer; hydrogen transfer; sesamol
المشرفين على المادة: 0 (Antioxidants)
0 (Benzodioxoles)
0 (Chromans)
0 (Free Radicals)
0 (Phenols)
1P9D0Z171K (Butylated Hydroxytoluene)
25013-16-5 (Butylated Hydroxyanisole)
94IEA0NV89 (sesamol)
S18UL9710X (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid)
تواريخ الأحداث: Date Created: 20200726 Date Completed: 20210317 Latest Revision: 20210317
رمز التحديث: 20240628
مُعرف محوري في PubMed: PMC7397082
DOI: 10.3390/molecules25143300
PMID: 32708143
قاعدة البيانات: MEDLINE