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Synthesis and biological evaluation of some 1, 3‐benzoxazol ‐2( 3H )‐one hybrid molecules as potential antioxidant and urease inhibitors
Author(s) -
Yilmaz Fatih,
Menteşe Emre,
Sökmen Bahar Bilgin
Publication year - 2021
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.4165
Subject(s) - chemistry , benzoxazole , trolox , abts , isatin , coumarin , antioxidant , ebselen , stereochemistry , nuclear chemistry , organic chemistry , dpph , catalase , glutathione peroxidase
A new series of 1,3‐benzoxazol‐2( 3H )‐one hybrid compounds, including coumarin, isatin 1,3,4‐triazole and 1,3,4‐thiadiazole moieties, were synthesized and biologically evaluated for their antioxidant capacities and anti‐urease properties. The synthesized benzoxazole‐coumarin ( 6a–e ) and benzoxazole‐isatin ( 10a–c ) hybrids showed remarkable urease inhibitory activities with IC 50 (μM), ranging from 0.0306 ± 0.0030 to 0.0402 ± 0.0030, while IC 50 of standard thiourea is 0.5027 ± 0.0293. The synthesized benzoxazole‐triazole ( 8a–c ) and benzoxazole‐thiadiazole ( 9a–c ) hybrids showed similar urease inhibitory activities with IC 50 (μM), ranging from 0.3861 ± 0.0379 to 0.5126 ± 0.0345. The antioxidant activity of the synthesized compounds was evaluated for their antioxidant activities, such as reducing power and ABTS (2,2′‐azino‐bis(3‐ethylbenzothiazoline‐6‐sulphonic acid) diammonium salt) radical scavenging. The results of ABTS radical scavenging activities of some of the synthesized molecules showed higher activities than standard Trolox, SC 50 (μM) = 213.04 ± 18.12. One benzoxazole‐coumarin ( 6f ), two benzoxazole‐isothiocyanate ( 7b, 7c ), and two benzoxazole‐triazole ( 8b, 8c ) derivatives showed higher activities (SC 50 (μM) values, 82.07 ± 10.34, 120.19 ± 7.30, 104.58 ± 10.55, 153.26 ± 7.14, and 144.82 ± 10.68, respectively) than standard Trolox, (SC 50 (μM) = 213.04 ± 18.12).