Synthesis and biological evaluation of some 1,3‐benzoxazol‐2(3H)‐one hybrid molecules as potential antioxidant and urease inhibitors

Abstract

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 IC50 (μM), ranging from 0.0306 ± 0.0030 to 0.0402 ± 0.0030, while IC50 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 IC50 (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, SC50 (μM) = 213.04 ± 18.12. One benzoxazole‐coumarin (6f), two benzoxazole‐isothiocyanate (7b, 7c), and two benzoxazole‐triazole (8b, 8c) derivatives showed higher activities (SC50 (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, (SC50 (μM) = 213.04 ± 18.12).

Urease Inhibition and Structure‐Activity Relationship Study of Thiazolidinone‐, Triazole‐, and Benzothiazole‐Based Heterocyclic Derivatives: A Focus Review

“…Yilmaz and coauthors [99] synthesized new analogs of 1,3benzoxazol-2(3H)-one containing 1,3,4-triazole (36) and tested their urease inhibition potency (Canavalia ensiformis). Results found that all the screened derivatives exhibited superior potency (IC 50 = 0.0307-0.0367 μM) than the used standard; thiourea (IC 50 = 0.5027 μM).…”

Synthesis of quinazolinone derivatives containing an acyl hydrazone skeleton as potent anti-urease agents enzyme kinetic studies and anti-oxidant properties

“…The IC 50 values reported in many urease enzyme inhibition studies in the literature are close and similar to the results we have obtained. [12][13][14][15][16][20][21][22]…”

“…According to recent studies, several quinazolinone derivatives with diverse side groups have anti-urease activity. [11][12][13][14][15][16] In our recent studies, we investigated quinazolinone derivatives, that were very active inhibitors of jack bean urease. However, there is still a considerable need for alternative or novel treatments of H. pylori associated with diseases.…”

Diverse and efficient catalytic applications of new cockscomb flower-like Fe3O4@SiO2@KCC-1@MPTMS@CuIImesoporous nanocomposite in the environmentally benign reduction and reductive acetylation of nitroarenes and one-pot synthesis of some coumarin compounds

“…These scaffolds have diverse biological properties including anticancer, 10 antioxidant, 11 antidepressant, 12 antimicrobial, 13 anti-nociceptive, 14 anti-asthmatic, 15 anti-inflammatory, 16 anti-pyretic, 17 antileishmanial, 18 anti-coagulant, 19 anti-tubercular, 20 antiviral, 21 antibacterial, 22 antifungal, 23 antimalarial, 24 antidiabetic, 25 anti-hepatitis C virus, 26 anti-HIV, 27 anti-proliferative, 28 antiplatelet, 29 and antiplasmodial 30 activities. They are also well-known inhibitors of urease, 31 acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), 32 cyclooxygenase (COX), 33 lipoxygenase (LOX), 34 monoamine oxidases A and B (MAO-A and MAO-B), 35 tubulin polymerization, 36 carbonic anhydrase, 37 α-glucosidase, 38 inositol-requiring enzyme 1 (IRE-1) RNase, 39 mitochondria-targeting antitumor STAT3, 40 selective cyclin-dependent kinase 9 (CDK9), 41 selective aldehyde dehydrogenase 1A1, 42 coagulation factor XIIa (FXIIa), 43 casein kinase 2 (CK2), 44 steroid sulfatase (STS), 45 chitin synthase (CHS), 46 etc. These heterocyclic scaffolds have antagonistic behavior against chemokine-like factor 1 (CKLF1), 47 G-protein-coupled receptor 35 (GPR35), 48 orphan G-protein-coupled receptor 55 (GPR55), 49 A 3 adenosine receptor, 50 and many others.…”