A one-pot domino synthesis and discovery of highly functionalized dihydrobenzo[b]thiophenes as AChE inhibitors

Jeyachandran, Veerappan; Kumar, Raju Ranjith; Ali, Mohamed Ashraf; Choon, Tan Soo

doi:10.1016/j.bmcl.2013.01.122

Cited by 23 publications

(8 citation statements)

References 14 publications

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“…Organosulfur molecules are ubiquitous structural motifs found in varieties of bioactive natural products as well as pharmaceuticals and functional materials . In particular, dihydrobenzo[b]thiophenes are distributed with significant applications in many medicinal compounds, such as analgesic agents, antifungal agents, Na + /H + antiporter inhibitors, acetylcholinesterase inhibitors, and peroxisome proliferator-activated receptor γ agonists (Figure ). Therefore, the search for constructing C–S bonds has received great attention, and numerous methods for the formation of C–S bonds have been developed …”

Section: Introductionmentioning

confidence: 99%

Copper-Catalyzed Cycloaddition of Heterobicyclic Alkenes with Diaryl Disulfides to Synthesize Dihydrobenzo[b]thiophene Derivatives

et al. 2021

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A novel copper-catalyzed cycloaddition of diaryl disulfides to heterobicyclic alkenes has been developed. The CS and CC bonds can be formed simultaneously on the CC bond of the olefins via a single-step cycloaddition to afford a series of 2,3-dihydrobenzo[b]thiophene derivatives. This reaction exhibits excellent diastereoselectivity and relatively broad substrate scope. Various functional groups attached to the substrates are tolerated in this protocol to give the corresponding exo adducts in moderate yields.

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Section: Introductionmentioning

confidence: 99%

Copper-Catalyzed Cycloaddition of Heterobicyclic Alkenes with Diaryl Disulfides to Synthesize Dihydrobenzo[b]thiophene Derivatives

et al. 2021

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“…Dihydrobenzo [b]thiophenes 323 exhibiting acetylcholinesterase (AChE) inhibitory activity were obtained by a multi-step domino reaction that involved a Knoevenagel condensation/Michael addition/intramolecular Thorpe-Ziegler cyclization/tautomerization/elimination sequence (Scheme 74). 70 Screening of the products revealed that they had moderate AChE inhibitory activity.…”

Section: Review Synthesismentioning

confidence: 99%

Synthesis of Biologically Active Heterocycles via a Domino Sequence Involving an SN2/Thorpe–Ziegler Reaction Step

et al. 2021

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“…compound [(G3)-Mor] [37]; acts as an muscarinic receptor 1 agonist; enhances memory function in Alzheimer's type dementia animal models; and modulates APP secretion [38,39]. It became evident that various thiophene (Figure 4) conjugates were potential AChE inhibitors [40][41][42]. Erucic acid ( Figure 4) is a monounsaturated omega-9 fatty acid present in wallflower seed, rapeseed oil and canola (20-54%), and in mustard oil (42%).…”

Section: Conjugated Moieties (Piperidine Morpholine Thiophene and Ementioning

confidence: 99%

Multi-targeted directed ligands for Alzheimer’s disease: design of novel lead coumarin conjugates

Repsold

Malan

Joubert

et al. 2018

SAR and QSAR in Environmental Research

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Alzheimer's Disease (AD) is a neurodegenerative disease characterized by central nervous system insults with progressive cognitive (memory, attention) and non-cognitive (anxiety, depression) impairments. Pathophysiological events affect predominantly cholinergic neuronal loss and dysfunctions of the dopaminergic system. The aim of the current study was to design multi-targeted directed lead structures based on the coumarin scaffold with inhibitory properties at two key enzymes in disease relevant systems, i.e. acetylcholinesterase (AChE) and monoamine oxidase B (MAO-B). Conventional and microwave synthetic methods were utilized to synthesize coumarin scaffold-based novel morpholino, piperidino, thiophene and erucic acid conjugates. Biological assays indicated that the coumarin-morpholine ether conjugate BPR 10 was the most potent hMAO-B inhibitor. The coumarin-piperidine conjugates BPR 13 and BPR 12 were the most potent inhibitors of eeAChE at 100 μM and 1 μM, respectively. Molecular modelling studies were conducted with Accelrys Discovery Studio V3.1.1 utilising the published hMAO-B (2V61) and hAChE (4EY7) crystal structures. Compound BPR 10 occupies both the entrance and substrate cavities of the active site of MAO-B. BPR 13 resides in both the peripheral anionic site (PAS) and the catalytic anionic site (CAS) of hAChE. This study demonstrated that the coumarin scaffold serves as a promising pharmacophore for MTDLs design.

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A one-pot domino synthesis and discovery of highly functionalized dihydrobenzo[b]thiophenes as AChE inhibitors

Cited by 23 publications

References 14 publications

Copper-Catalyzed Cycloaddition of Heterobicyclic Alkenes with Diaryl Disulfides to Synthesize Dihydrobenzo[b]thiophene Derivatives

Copper-Catalyzed Cycloaddition of Heterobicyclic Alkenes with Diaryl Disulfides to Synthesize Dihydrobenzo[b]thiophene Derivatives

Synthesis of Biologically Active Heterocycles via a Domino Sequence Involving an SN2/Thorpe–Ziegler Reaction Step

Multi-targeted directed ligands for Alzheimer’s disease: design of novel lead coumarin conjugates

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