New Conditions for the Effective Synthesis of Tri and Tetrasubstituted Imidazoles Catalysed by Recyclable Indium (III) Triflate and Magnesium Sulfate Heptahydrate

Karami, Bahador; Ferdosian, Roghayeh; Eskandari, Khalil

doi:10.3184/174751914x13863406090407

Cited by 13 publications

(3 citation statements)

References 26 publications

(9 reference statements)

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“…The progression of the reaction was monitored through TLC. On completion of the reaction confirmed through TLC, the mixture was diluted with excess MeOH and filtered to separate the catalyst, the filtrate was thus concentrated under vacuum and poured onto ice-cold solution of diluted MeOH, and the product was separated out as the precipitate, which was filtered, dried, and purified by column chromatography. − ,− …”

Section: Experimental Sectionmentioning

confidence: 99%

Novel Imidazole Phenoxyacetic Acids as Inhibitors of USP30 for Neuroprotection Implication via the Ubiquitin-Rho-110 Fluorometric Assay: Design, Synthesis, and In Silico and Biochemical Assays

Mandal

Kumar

Alam

et al. 2022

ACS Chem. Neurosci.

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USP30, a deubiquitinating enzyme family, forfeits the ubiquitination of E3 ligase and Parkin on the surface of mitochondria. Inhibition of USP30 results in mitophagy and cellular clearance. Herein, by understanding structural requirements, we discovered potential USP30 inhibitors from an imidazole series of ligands via a validated ubiquitin-rhodamine-110 fluorometric assay. A novel catalytic use of the Zn(l-proline)2 complex for the synthesis of tetrasubstituted imidazoles was identified. Among all compounds investigated, 3g and 3f inhibited USP30 at IC50 of 5.12 and 8.43 μM, respectively. The binding mode of compounds at the USP30 binding site was understood by a docking study and interactions with the key amino acids were identified. Compound 3g proved its neuroprotective efficacy by inhibiting apoptosis on SH-SY5Y neuroblastoma cells against dynorphin A (10 μM) treatment. Hence, the present study provides a new protocol to design and develop ligands against USP30, thereby offering a therapeutic strategy under conditions like kidney damage and neurodegenerative disorders including Parkinson’s disease.

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Section: Experimental Sectionmentioning

confidence: 99%

Novel Imidazole Phenoxyacetic Acids as Inhibitors of USP30 for Neuroprotection Implication via the Ubiquitin-Rho-110 Fluorometric Assay: Design, Synthesis, and In Silico and Biochemical Assays

Mandal

Kumar

Alam

et al. 2022

ACS Chem. Neurosci.

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“…Flavonoids and homoisoflavonoids (3‐benzylidene chroman‐4‐one) are important compounds with a broad spectrum of biological activities, such as the anti‐AChE activity, monoamine oxidase‐B inhibitory effect, corticosteroid inhibitory activity, anticancer, and antimicrobial properties, neuroprotection capability, amyloid‐β fibril formation inhibitory activity, and 15‐lipoxygenase inhibitory effect . In continuation of our research program on the efficient synthesis of newly prepared organic compounds, and potentially interesting biological active compounds, herein, we designed and synthesized novel series of chroman‐4‐one derivatives bearing aminoalkoxy moiety at the 7‐position of the 3‐benzylidene chroman‐4‐ones and evaluated their anti‐AChE and anti‐BuChE activities (Figure ). The cyclic aminoalkoxy part of designed molecules is found in some reported AChE inhibitors, such as ebselen and aurone derivatives …”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, biological evaluation, and molecular dynamics of novel cholinesterase inhibitors as anti‐Alzheimer's agents

Shamsimeymandi

Pourshojaei

Eskandari

et al. 2019

Archiv der Pharmazie

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A series of novel chroman-4-one derivatives were designed and synthesized successfully with good to excellent yield (3a-l). In addition, the obtained products were evaluated for their cholinesterase (ChE) inhibitory activities. The results show that among the various synthesized compounds, analogs bearing the piperidinyl ethoxy side chain with 4-hydroxybenzylidene on the 3-positions of chroman-4-one (3l) showed the most potent activity with respect to acetylcholinesterase (anti-AChE activity; IC 50 = 1.18 μM). In addition, the structure-activity relationship was studied and the results revealed that the electron-donating groups on the aryl ring of the 3benzylidene fragment (3k, 3l) resulted in the designed compounds to be more potent ChE inhibitors in comparison with those having electron-withdrawing groups (3h). In this category, the strongest ChE inhibition was found for the compound containing piperidine as cyclic amine, and a hydroxyl group (for AChE, compound 3l) and fluoro group (for butyrylcholinesterase (BuChE, compound 3i) on the para-position of the aryl ring of the benzylidene group. The molecular docking and dynamics studies of the most potent compounds (3i and 3l against BuChE and AChE, respectively) demonstrated remarkable interactions with the binding pockets of the ChE enzymes and confirmed the results obtained through in vitro experiments. K E Y W O R D S acetylcholinesterase, Alzheimer's disease, butyrylcholinesterase, chroman-4-one, molecular dynamics (MD)

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“…[9,10,36] Recently, solid supported catalysts have attracted significant interest because of their unique advantages including easy separation from the reaction mixture and reusability, [37][38][39] easy handling and storing, avoiding the generation of residual salts, nontoxicity, low solubility, increasing selectivity of the reactions, and high stability. [40][41][42] Very recently a green and recyclable inexpensive Brønsted base prepared and called silica sodium carbonate (SSC) 3, [43] via a cascade two steps method from silica gel (1) and silica chloride 2 (Scheme 1). SSC has several important advantages including environmentally benign, reusability, easy handling, high perdurability, and convenience work-up.…”

Section: Introductionmentioning

confidence: 99%

Ultrasound-assisted and Efficient Knoevenagel Condensation Reaction Catalyzed by Silica Sodium Carbonate Nanoparticles

et al. 2018

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An efficient and ultrasound-assisted route to the synthesis of arylidene malononitriles/methylciano-or ethylciano acetates in a onepot reaction catalyzed by silica sodium carbonate nanoparticles (SSC NPs) is described. In this reaction, SSC NPs demonstrated high efficiency as catalyst to obtain target products. By this achievement, a wide range of α,β-unsaturated compounds as Knoevenagel condensation products with good to excellent yields are obtained from reaction between numerous arylaldehydes, and malononitrile, methyl cianoacetate or ethyl cianoacetate. Target products which prepared in high yield and high purity can be candidate as important biologically active molecules. This method is an easy, cheap, rapid and highly efficient for the synthesis of desired products. In addition, capability of catalyst to separate from reaction mixture and reuse in further runs and being compatible with green chemistry are considered as other advantages of this procedure. All products were deduced from their FT-IR and FT-NMR spectroscopic and elemental analysis data.

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New Conditions for the Effective Synthesis of Tri and Tetrasubstituted Imidazoles Catalysed by Recyclable Indium (III) Triflate and Magnesium Sulfate Heptahydrate

Cited by 13 publications

References 26 publications

Novel Imidazole Phenoxyacetic Acids as Inhibitors of USP30 for Neuroprotection Implication via the Ubiquitin-Rho-110 Fluorometric Assay: Design, Synthesis, and In Silico and Biochemical Assays

Novel Imidazole Phenoxyacetic Acids as Inhibitors of USP30 for Neuroprotection Implication via the Ubiquitin-Rho-110 Fluorometric Assay: Design, Synthesis, and In Silico and Biochemical Assays

Design, synthesis, biological evaluation, and molecular dynamics of novel cholinesterase inhibitors as anti‐Alzheimer's agents

Ultrasound-assisted and Efficient Knoevenagel Condensation Reaction Catalyzed by Silica Sodium Carbonate Nanoparticles

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