Novel series of triazole containing coumarin and isatin based hybrid molecules as acetylcholinesterase inhibitors

Bhagat, Kavita; Singh, Jatinder; Sharma, Aakriti; Kaur, Avneet; Kumar, Nitish; Gulati, Harmandeep Kaur; Singh, Atamjit; Singh, Harbinder; Bedi, Preet Mohinder Singh

doi:10.1016/j.molstruc.2021.131085

Cited by 21 publications

(15 citation statements)

References 55 publications

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“…SAR studies revealed that the presence of an electronegative group such as F, Cl, or NO 2 on the benzoyl ring improves AChE inhibition. These two hit/lead molecules may be further optimized to obtain potent AChEIs [ 123 ].…”

Section: Conjugates Of 123-triazole As Potential Ache and Buche Inhib...mentioning

confidence: 99%

An Overview of 1,2,3-triazole-Containing Hybrids and Their Potential Anticholinesterase Activities

Khan¹,

Akhtar²,

Gogoi

et al. 2023

Pharmaceuticals

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Acetylcholine (ACh) neurotransmitter of the cholinergic system in the brain is involved in learning, memory, stress responses, and cognitive functioning. It is hydrolyzed into choline and acetic acid by two key cholinesterase enzymes, viz., acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). A loss or degeneration of cholinergic neurons that leads to a reduction in ACh levels is considered a significant contributing factor in the development of neurodegenerative diseases (NDs) such as Alzheimer’s disease (AD). Numerous studies have shown that cholinesterase inhibitors can raise the level of ACh and, therefore, enhance people’s quality of life, and, at the very least, it can temporarily lessen the symptoms of NDs. 1,2,3-triazole, a five-membered heterocyclic ring, is a privileged moiety, that is, a central scaffold, and is capable of interacting with a variety of receptors and enzymes to exhibit a broad range of important biological activities. Recently, it has been clubbed with other pharmacophoric fragments/molecules in hope of obtaining potent and selective AChE and/or BuChE inhibitors. The present updated review succinctly summarizes the different synthetic strategies used to synthesize the 1,2,3-triazole moiety. It also highlights the anticholinesterase potential of various 1,2,3-triazole di/trihybrids reported in the past seven years (2015-2022), including a rationale for hybridization and with an emphasis on their structural features for the development and optimization of cholinesterase inhibitors to treat NDs.

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Section: Conjugates Of 123-triazole As Potential Ache and Buche Inhib...mentioning

confidence: 99%

An Overview of 1,2,3-triazole-Containing Hybrids and Their Potential Anticholinesterase Activities

Khan¹,

Akhtar²,

Gogoi

et al. 2023

Pharmaceuticals

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“…Inspired from the biological efficacy of coumarin moiety [74,75] and 1,2,3-triazole nucleus, Dongamanti et al designed and synthesized dimers of coumarin and 1,2,3-triazole hybrids bearing alkyl spacer. The compounds were evaluated for antifungal activity against the Candida albicans and amongst all the compounds, 45 was emerge as most potent antifungal agent with MIC value of 20.95 μmol/mL.…”

Section: 23-triazole Derivatives Containing Coumarin Moietymentioning

confidence: 99%

1,2,3‐Triazole Derivatives as an Emerging Scaffold for Antifungal Drug Development against Candida albicans: A Comprehensive Review

Singh

Sharma

et al. 2023

Chemistry & Biodiversity

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Candida infections are most prominent among fungal infections majorly target immunocompromised and hospitalized patients and cause significant morbidity and mortality. Candida albicans is the notorious and most prevalent among all pathogenic Candida strains. Its emerging resistance toward available antifungal agents making it hard to tackle and emerging as global healthcare emergency. Simultaneously, 1,2,3-triazole nucleus is a privileged scaffold that is gaining importance in antifungal drug development due to being a prominent bioactive linker and isostere of triazole based antifungal class core 1,2,4-triazole. Numerous reports have been updated in scientific literature in last few decades related to utilization of 1,2,3-triazole nucleus in antifungal drug development against Candida albicans. Present review will shed light on various preclinical studies focused on development of 1,2,3-triazole derivatives targeting Candida albicans along with brief highlight on clinical trials and newly approved drugs. Structure-activity relationship has been precisely discussed for each architect along with future perspective that will help medicinal chemists in design and development of potent antifungal agents for tackling infections derived from Candida albicans.

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“…On the other hand, isatin (1H-indol-2,3-dione), a privileged structure, and its derivatives have received special attention among medicinal chemists since they can be used as starting materials for the synthesis of heterocycles with potential bioactivities [23][24][25]. During last decades, a large number of isatin derivatives have been reported to exhibit a wide range of biological activities [26][27][28][29][30][31][32][33][34].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, in-vitro biological evaluation, and molecular docking study of novel spiro-β-lactam-isatin hybrids

et al. 2022

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In our ongoing search for bioactive compounds, a class of novel spiro-β-lactam isatin hybrids has been synthesized through a [2+2] cycloaddition reaction from 1-allyl-3-(arylimino)indolin-2-one, ketenes and various aryloxy acetic acids. The formation of all cycloadducts was confirmed by FTIR, 1 H NMR, 13 C NMR, and mass spectroscopy as well as elemental analyses. The new βlactams were subsequently evaluated for their biological activities demonstrating moderate to good activities against P. falciparum K1 strain. Among them, 4b and 4e lead to the best results with IC 50 of 5.04 and 7.18 µM, respectively. The molecular docking simulation of 4b with P. falciparum dihydrofolate reductase enzyme (PfDHFR) binding site presented several important intermolecular interactions. All the synthesized β-lactams were also evaluated for their antimicrobial activities against both Gram-positive (S. aureus ATCC 25923) and Gram-negative bacteria (E. coli ATCC 28922, P. aeruginosa ATCC 27853) but unfortunately MICs up to 200 µg/mL were encountered in all cases.

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Novel series of triazole containing coumarin and isatin based hybrid molecules as acetylcholinesterase inhibitors

Cited by 21 publications

References 55 publications

An Overview of 1,2,3-triazole-Containing Hybrids and Their Potential Anticholinesterase Activities

An Overview of 1,2,3-triazole-Containing Hybrids and Their Potential Anticholinesterase Activities

1,2,3‐Triazole Derivatives as an Emerging Scaffold for Antifungal Drug Development against Candida albicans: A Comprehensive Review

Synthesis, in-vitro biological evaluation, and molecular docking study of novel spiro-β-lactam-isatin hybrids

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