1H-1,2,3-triazole grafted tacrine-chalcone conjugates as potential cholinesterase inhibitors with the evaluation of their behavioral tests and oxidative stress in mice brain cells

Rani, Anu; Singh, Amandeep; Kaur, Jashanpreet; Singh, Gurjit; Bhatti, Rajbir; Gumede, Njabulo Joyfull; Kisten, Prishani; Singh, Pushpinder; Sumanjit,; Kumar, Vipan

doi:10.1016/j.bioorg.2021.105053

Cited by 17 publications

(14 citation statements)

References 52 publications

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“…In vivo assays and biochemical analysis of oxidative stress factors showed that the most promising compounds induce a substantial reversal of scopolamine-induced oxidative stress. Molecular docking studies of compounds 69h and 69i in the active site of AChE confirm the interaction of these compounds with residues of this enzyme [ 112 ].…”

Section: Other Activitiesmentioning

confidence: 97%

“…Considering the potential of tacrine, which was used for the treatment of AD, and aiming to develop new compounds using this moiety in combination with chalcones, also known for their neuroprotective potential, Rani et al (2021) reported the synthesis of a series of 1,2,3-triazole-linked chalcone- and ferrocenylchalcone-tacrine conjugates and their anti-AChE activity [ 112 ]. The Click Chemistry step from corresponding chalcone azides and propargylated tacrine achieved the desired compounds in 64–78% yield.…”

Section: Other Activitiesmentioning

confidence: 99%

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Recent Advances in Bioactive Flavonoid Hybrids Linked by 1,2,3-Triazole Ring Obtained by Click Chemistry

et al. 2021

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As a result of the biological activities of natural flavonoids, several synthetic strategies aiming to obtain analogues with improved potency and/or pharmacokinetic profile have been developed. Since the triazole ring has been associated with several biological activities and metabolic stability, hybridization with a 1,2,3-triazole ring has been increasingly reported over the last years. The feasible synthesis through copper (I) catalyzed azide-alkyne cycloaddition (CuAAC) has allowed the accomplishment of several hybrids. Since 2017, almost 700 flavonoid hybrids conjugated with 1,2,3-triazole, including chalcones, flavones, flavanones and flavonols, among others, with antitumor, antimicrobial, antidiabetic, neuroprotective, anti-inflammatory, antioxidant, and antifouling activity have been reported. This review compiles the biological activities recently described for these hybrids, highlighting the mechanism of action and structure–activity relationship (SAR) studies.

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Section: Other Activitiesmentioning

confidence: 97%

Section: Other Activitiesmentioning

confidence: 99%

Recent Advances in Bioactive Flavonoid Hybrids Linked by 1,2,3-Triazole Ring Obtained by Click Chemistry

et al. 2021

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“…Only compound 146 attained 50% inhibition at 10 µM concentration against the AChE enzyme. An IC 50 value of 5.328 µM was obtained for compound 146, indicating that these hybrid analogs are selective inhibitors of the AChE enzyme 224 ( Table 5 ).…”

Section: Synthetic Cholinesterase Inhibitorsmentioning

confidence: 99%

Inhibitory potential of nitrogen, oxygen and sulfur containing heterocyclic scaffolds against acetylcholinesterase and butyrylcholinesterase

et al. 2022

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“…Many of them had tacrine as a structural scaffold (thienothiazines, thiazoles, quinuclidines, benzofuranes, quinolines, etc. ), but many other structural scaffolds were also used, as well as hybrids containing galantamine, donepezil and rivastigmine as moieties [ 14 , 15 , 16 , 17 , 18 , 19 , 20 ]. However, so far, no drug that is a selective BChE inhibitor has been approved for the treatment of AD.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Biological Evaluation of Biscarbamates as Potential Selective Butyrylcholinesterase Inhibitors for the Treatment of Alzheimer’s Disease

et al. 2022

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As butyrylcholinesterase (BChE) plays a role in the progression of symptoms and pathophysiology of Alzheimer’s disease (AD), selective inhibition of BChE over acetylcholinesterase (AChE) can represent a promising pathway in treating AD. The carbamate group was chosen as a pharmacophore because the carbamates currently or previously in use for the treatment of AD displayed significant positive effects on cognitive symptoms. Eighteen biscarbamates with different substituents at the carbamoyl and hydroxyaminoethyl chain were synthesized, and their inhibitory potential toward both cholinesterases and inhibition selectivity were determined. The ability of carbamates to cross the blood–brain barrier (BBB) by passive transport, their cytotoxic profile and their ability to chelate biometals were also evaluated. All biscarbamates displayed a time-dependent inhibition with inhibition rate constants within 10−3–10−6 M−1 min−1 range for both cholinesterases, with generally higher preference to BChE. For two biscarbamates, it was determined that they should be able to pass the BBB by passive transport, while for five biscarbamates, this ability was slightly limited. Fourteen biscarbamates did not exhibit a cytotoxic effect toward liver, kidney and neuronal cells. In conclusion, considering their high BChE selectivity, non-toxicity, ability to chelate biometals and pass the BBB, compounds 2 and 16 were pointed out as the most promising compounds for the treatment of middle and late stages of AD.

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1H-1,2,3-triazole grafted tacrine-chalcone conjugates as potential cholinesterase inhibitors with the evaluation of their behavioral tests and oxidative stress in mice brain cells

Cited by 17 publications

References 52 publications

Recent Advances in Bioactive Flavonoid Hybrids Linked by 1,2,3-Triazole Ring Obtained by Click Chemistry

Recent Advances in Bioactive Flavonoid Hybrids Linked by 1,2,3-Triazole Ring Obtained by Click Chemistry

Inhibitory potential of nitrogen, oxygen and sulfur containing heterocyclic scaffolds against acetylcholinesterase and butyrylcholinesterase

Design, Synthesis and Biological Evaluation of Biscarbamates as Potential Selective Butyrylcholinesterase Inhibitors for the Treatment of Alzheimer’s Disease

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