A new series of asymmetric bis-isatin derivatives containing urea/thiourea moiety: Preparation, spectroscopic elucidation, antioxidant properties and theoretical calculations

Yakan, Hasan; ÇAVUŞ, Muhammet Serdar; Kurt, Belma Zengin; MUĞLU, Halit; Sönmez, Fatih; Güzel, Emre

doi:10.1016/j.molstruc.2021.130495

A new series of asymmetric bis-isatin derivatives containing urea/thiourea moiety: Preparation, spectroscopic elucidation, antioxidant properties and theoretical calculations

Yazarlar (6)

Doç. Dr. Hasan Yakan Ondokuz Mayıs Üniversitesi, Türkiye

Prof. Dr. Muhammet Serdar ÇAVUŞ Kastamonu Üniversitesi, Türkiye

Prof. Dr. Belma Zengin Kurt Bezmiâlem Vakıf Üniversitesi, Türkiye

Prof. Dr. Halit MUĞLU Kastamonu Üniversitesi, Türkiye

Prof. Dr. Fatih Sönmez Sakarya University Of Applied Sciences, Türkiye

Prof. Dr. Emre Güzel Sakarya Uygulamalı Bilimler Üniversitesi, Türkiye

Makale Türü	Özgün Makale (SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale)
Dergi Adı	Journal of Molecular Structure
Dergi ISSN	0022-2860 Wos Dergi Scopus Dergi
Dergi Tarandığı Indeksler	SCI
Makale Dili	İngilizce	Basım Tarihi	09-2021
Cilt / Sayı / Sayfa	1239 / 1 / –	DOI	10.1016/j.molstruc.2021.130495
Makale Linki	http://dx.doi.org/10.1016/j.molstruc.2021.130495

Özet

In the present study, design, synthesis, characterization, and investigation of antioxidant properties of novel asymmetric bis-isatin derivatives (1-8) containing urea/thiourea moiety are reported for the first time. FT-IR, ¹H-NMR, and ¹³C-NMR spectroscopic methods and elemental analysis were used to elucidate the structures of the synthesized compounds. Their CUPRAC and ABTS cation radical scavenging abilities were investigated for antioxidant activity. The bis-isatins containing urea moiety (compounds 1-4) did not show ABTS activity, while those containing the thiourea moiety (compounds 5-8) showed moderate ABTS activity. Besides, all bis-isatins were observed to exhibit CUPRAC activity at a low micromolar level The 1-(5-chloro-2-oxoindolin-3-ylidene)-5-(2-oxoindolin-3-ylidene)thiocarbonohydrazide (compound 5) showed the highest ABTS activity with IC50 value of 18.44 µM; on the other hand, the 1-(5-chloro-2-oxoindolin-3-ylidene)-5-(5-methoxy-2-oxoindolin-3-ylidene)carbonohydrazide (compound 2) had the strongest CUPRAC activity with A0.50 value of 0.600 µM. Both spectroscopic and antioxidant properties of the compounds were examined computationally, and the structure-activity relationship was investigated theoretically by comparing with experimental data. The ground state geometries and chemical reactivity parameters of the compounds were calculated using the B3LYP hybrid functional with 6-311++g(2d,2p) and 6-31g(d) basis sets. After determining the local electron affinity of the compounds, the Laplacian bond order and intrinsic bond strength indexes (independent gradient model-δg^IGMH and IBSI^IGMH descriptors based on Hirshfeld approach) of hydrogen bonds at possible reactive sites were calculated and associated with the antioxidant properties of the compounds.

Anahtar Kelimeler

Science Direct

BM Sürdürülebilir Kalkınma Amaçları

Atıf Sayıları
Scopus	28

A new series of asymmetric bis-isatin derivatives containing urea/thiourea moiety: Preparation, spectroscopic elucidation, antioxidant properties and theoretical calculations

Dergi Adı	Journal of Molecular Structure
Yayıncı	Elsevier B.V.
Açık Erişim	Hayır
ISSN	0022-2860
E-ISSN	1872-8014
CiteScore	8,0
SJR	0,628
SNIP	0,999

A new series of asymmetric bis-isatin derivatives containing urea/thiourea moiety: Preparation, spectroscopic elucidation, antioxidant properties and theoretical calculations

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