Synthesis, structure elucidation, antioxidant properties, and theoretical calculations of new Schiff bases–isatin derivatives

BAKIR, Temel Kan; ÇAVUŞ, Muhammet Serdar; MUĞLU, Halit; Yakan, Hasan

doi:10.1007/s11164-024-05318-1

Synthesis, structure elucidation, antioxidant properties, and theoretical calculations of new Schiff bases–isatin derivatives

Yazarlar (4)

Prof. Dr. Temel Kan BAKIR Kastamonu Üniversitesi, Türkiye

Prof. Dr. Muhammet Serdar ÇAVUŞ Kastamonu Üniversitesi, Türkiye

Prof. Dr. Halit MUĞLU Kastamonu Üniversitesi, Türkiye

Doç. Dr. Hasan Yakan Ondokuz Mayis Üniversitesi, Türkiye

Makale Türü	Özgün Makale (SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale)
Dergi Adı	Research on Chemical Intermediates (Q2)
Dergi ISSN	0922-6168 Wos Dergi Scopus Dergi
Dergi Tarandığı Indeksler	SCI-Expanded
Makale Dili	İngilizce	Basım Tarihi	06-2024
Cilt / Sayı / Sayfa	50 / 8 / 3937–3962	DOI	10.1007/s11164-024-05318-1
Makale Linki	http://dx.doi.org/10.1007/s11164-024-05318-1

Özet

Isatin-derived Schiff bases are the subject of many studies, finding wide application areas in polymer technology, pharmaceutical industry, and medicine. In this study, a series of new Schiff bases were prepared from monothiocarbohydrazones based on isatins with different substituents (5-F, 5-Br, 5-I, and 5-MeO). The chemical structures of the synthesized compounds were determined using ¹H NMR, ¹³C NMR, FTIR spectroscopic techniques, and elemental analysis. Antioxidant activity determinations of 23 compounds were performed using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical quenching method. The highest percent inhibition value at 10 µM concentration was shown by compound number 22, 5-bromoisatin Schiff base containing 3-methoxy-4-hydroxy group. Compound 17, a 5-iodoisatin Schiff base containing 3-methoxy-4-hydroxy group, showed the highest antioxidant activity with an IC50 value of 9.76 ± 0.03 µM. In addition to the theoretical analysis of the compounds, both their spectroscopic and antioxidant properties were investigated. The ground-state geometries and some chemical reactivity parameters of the compounds were calculated using the B3LYP/6-311 + + G(2d,2p) approach. Besides intramolecular interactions, substituent effects, and some QTAIM parameters, the calculations were also performed to study the electronic properties of reactive N/O–H bonds and were used to interpret the experimental results. The effects of the electronic parameters and intramolecular interactions of reactive N/O–H bonds on the antioxidant properties of the compounds were investigated. Additionally, the relationships of DPPH reactions with delocalization indices of N/O-H bonds and the pattern of SET/HAT mechanisms with electronic variables were analyzed. Examination of electron and hydrogen atom transfer mechanisms has shown the dominance of electron transfer, supported by the correlation coefficients between IC50 values and SET reaction energies.

Anahtar Kelimeler

13C NMR | Antioxidant activity | DFT studies | Thiocarbohydrazone

BM Sürdürülebilir Kalkınma Amaçları

Atıf Sayıları
Scopus	19

Synthesis, structure elucidation, antioxidant properties, and theoretical calculations of new Schiff bases–isatin derivatives

Dergi Adı	RESEARCH ON CHEMICAL INTERMEDIATES
Yayıncı	Springer Netherlands
Açık Erişim	Hayır
ISSN	0922-6168
E-ISSN	1568-5675
CiteScore	5,7
SJR	0,528
SNIP	0,724

Synthesis, structure elucidation, antioxidant properties, and theoretical calculations of new Schiff bases–isatin derivatives

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