Synthesis and anticholinesterase activities of novel glycosyl benzoxazole derivatives

Wu, Yu-Ran; Ren, Shuting; Wang, Lei; Wang, You-Xian; Liu, Shu-Hao; Liu, Weiwei; Shi, Da–Hua; Cao, Zhiling

doi:10.1177/1747519819901251

Cited by 7 publications

(2 citation statements)

References 21 publications

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“…After this, a docking study was conducted using the optimized enzyme and analogue structures. Our earlier investigations contain all of the detailed information about the docking process [ 54 , 55 , 56 ].…”

Section: Methodsmentioning

confidence: 99%

Investigation of Novel Benzoxazole-Oxadiazole Derivatives as Effective Anti-Alzheimer’s Agents: In Vitro and In Silico Approaches

et al. 2023

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Alzheimer’s disease (AD) is a progressive neurological illness that is distinguished clinically by cognitive and memory decline and adversely affects the people of old age. The treatments for this disease gained much attention and have prompted increased interest among researchers in this field. As a springboard to explore new anti-Alzheimer’s chemical prototypes, the present study was carried out for the synthesis of benzoxazole-oxadiazole analogues as effective Alzheimer’s inhibitors. In this research work, we have focused our efforts to synthesize a series of benzoxazole-oxadiazole (1–19) and evaluating their anti-Alzheimer properties. In addition, the precise structures of synthesized derivatives were confirmed with the help of various spectroscopic techniques including 1H-NMR, 13C-NMR and HREI-MS. To find the anti-Alzheimer potentials of the synthesized compounds (1–19), in vitro acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), inhibitory activities were performed using Donepezil as the reference standard. From structure-activity (SAR) analysis, it was confirmed that any variation found in inhibitory activities of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes were due to different substitution patterns of substituent(s) at the variable position of both acetophenone aryl and oxadiazole aryl rings. The results of the anti-Alzheimer assay were very encouraging and showed moderate to good inhibitory potentials with IC50 values ranging from 5.80 ± 2.18 to 40.80 ± 5.90 µM (against AChE) and 7.20 ± 2.30 to 42.60 ± 6.10 µM (against BuChE) as compared to standard Donepezil drug (IC50 = 33.65 ± 3.50 µM (for AChE) and 35.80 ± 4.60 µM (for BuChE), respectively. Specifically, analogues 2, 15 and 16 were identified to be significantly active, even found to be more potent than standard inhibitors with IC50 values of 6.40 ± 1.10, 5.80 ± 2.18 and 6.90 ± 1.20 (against AChE) and 7.50 ± 1.20, 7.20 ± 2.30 and 7.60 ± 2.10 (against BuChE). The results obtained were compared to standard drugs. These findings reveal that benzoxazole-oxadiazole analogues act as AChE and BuChE inhibitors to develop novel therapeutics for treating Alzheimer’s disease and can act as lead molecules in drug discovery as potential anti-Alzheimer agents.

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Section: Methodsmentioning

confidence: 99%

Investigation of Novel Benzoxazole-Oxadiazole Derivatives as Effective Anti-Alzheimer’s Agents: In Vitro and In Silico Approaches

et al. 2023

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“…Some benzoxazoles have been described as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors [ 19 , 20 , 21 , 22 ]. Recently, new glycosyl derivatives of benzoxazole were described as AChE inhibitors [ 23 ]. The most active compounds had IC 50 values against AChE and BChE at low µM levels [ 20 ].…”

Section: Introductionmentioning

confidence: 99%

Cholinesterases Inhibition, Anticancer and Antioxidant Activity of Novel Benzoxazole and Naphthoxazole Analogs

et al. 2022

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Benzoxazole and naphthoxazole fused systems are found in many biologically active molecules. Novel benzoxazole and naphthoxazole analogs functionalized by the 2,4-dihydroxyphenyl moiety were designed, obtained and evaluated as a broad spectrum of biological potency compounds. Sulfinylbis[(2,4-dihydroxyphenyl)methanethione] or its analogs and 2-aminophenols or 1-amino-2-naphthol were used as starting reagents. 4-(Naphtho[1,2-d][1,3]oxazol-2-yl)benzene-1,3-diol was identified as the most promising compound of the nanomolar activity against AChE (IC50 = 58 nM) of the mixed-type inhibition and of the moderate activity against BChE (IC50 = 981 nM). The higher antiproliferative potency against a panel of human cancer cell lines for naphtho[1,2-d][1,3]oxazoles than for benzoxazoles was found. The activity of the analog with chlorine atom was in the range of 2.18–2.89 µM (IC50) against all studied cells and it is similar to that of cisplatin studied comparatively. Moreover, this compound was not toxic at this concentration to human normal breast cells and keratinocytes. For some compounds it also has proved antioxidant properties at the level of IC50 = 0.214 µM, for the most active compound. The lipophilicity of all compounds, expressed as log p values, is within the range recommended for potential drugs. The biological activity profile of the considered analogs and their lipophilic level justify the search for agents used in AD or in anticancer therapy in this group of compounds.

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Synthesis of 2‐Amino Benzazoles Through Elemental Selenium‐Promoted Cyclization of Ortho‐Substituted Anilines and Isocyanides

Ding,

Ma,

Shi

et al. 2024

Eur J Org Chem

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A facile and transition metal‐free method has been developed for the synthesis of 2‐amino benzazoles through elemental selenium promoted cyclization reaction of ortho‐substituted anilines with isocyanides under mild conditions. Through this strategy, a series of 2‐amino benzooxa/(thia)zoles and benzimidazoles could be efficiently obtained in good to excellent yields with favorable functional group tolerance.

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Synthesis and anticholinesterase activities of novel glycosyl benzoxazole derivatives

Cited by 7 publications

References 21 publications

Investigation of Novel Benzoxazole-Oxadiazole Derivatives as Effective Anti-Alzheimer’s Agents: In Vitro and In Silico Approaches

Investigation of Novel Benzoxazole-Oxadiazole Derivatives as Effective Anti-Alzheimer’s Agents: In Vitro and In Silico Approaches

Cholinesterases Inhibition, Anticancer and Antioxidant Activity of Novel Benzoxazole and Naphthoxazole Analogs

Synthesis of 2‐Amino Benzazoles Through Elemental Selenium‐Promoted Cyclization of Ortho‐Substituted Anilines and Isocyanides

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