Azolylimidazoles: Synthetic strategies and medicinal applications

Abdel‐Wahab, Bakr F.; Khidre, Rizk E.

doi:10.3906/kim-1304-35

Cited by 8 publications

(3 citation statements)

References 13 publications

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“…On the other hand, it is well known that hydrazone derivatives also act as AChE, BChE and tyrosinase inhibitors [15d,28e, 29b, 34] . Apart from that, they indicate various biological activities such as analgesic and anti‐inflammatory [35a–b] …”

Section: Introductionmentioning

confidence: 99%

Design, Docking, Synthesis and Biological Evaluation of Novel Nicotinohydrazone Derivatives as Potential Butyrylcholinesterase Enzyme Inhibitor

2022

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In this research, some new heterocyclic hydrazone compounds bearing an aryl sulfonate moiety (2 a-i) were facilely synthesized for the first time and elucidated by some spectroscopic techniques (FT-IR, 1 H-and 13 C NMR). The inhibitory potentials of all synthesized molecules on acetylcholinesterase (AChE), butyrylcholinesterase (BChE), tyrosinase enzymes were investigated. Also, DPPH, ABTS and CUPRAC antioxidant activities of all molecules were examined. In BChE assay, it was determined that 2-Formylphenyl 4-chlorobenzenesulfonate (1 a) (IC 50 = 10.45 μM), 5-(diethylamino)-2-formylphenyl 4-Chlorobenzenesulfonate(1 h) (IC 50 = 10.12 μM), and 1-((2-Nicotinoylhydrazono)methyl)naphthalen-2-yl 4-chlorobenzene-sulfonate (2 i) (IC 50 = 9.89 μM) were found to be more effective than the standard compound galanthamine and donepezil. In DPPH assay, 2-((2-Nicotinoylhydrazono)methyl)phenyl 4-chlorobenzenesulfonate (2 a) (IC 50 = 361.03 μM) and 5-Methoxy-2-((2-nicotinoylhydrazono)methyl)phenyl 4-chlorobenzenesulfonate (2 e) (IC 50 = 348.9 μM) indicated the highest antioxidant activities. On the other hand, the molecular electrostatic potential (MEP) maps of compounds 1 a, 1 h, 2 i and galanthamine molecules were investigated. The molecular docking study for BChE enzyme structure was found to be compatible with the experimental results and MEP maps.

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Section: Introductionmentioning

confidence: 99%

Design, Docking, Synthesis and Biological Evaluation of Novel Nicotinohydrazone Derivatives as Potential Butyrylcholinesterase Enzyme Inhibitor

2022

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“…The pyrazoles possessing a formyl group –CHO at the 4‐position are versatile organic synthetic intermediates for the synthesis of many heterocyclic ring systems such as pyrazolylpyrazolines , pyrazoloquinolinones , 4 H ‐pyrazolopyran , pyrazolylbenzoxazole , pyrazolothiadiazepines , pyrazolyloxazolone , pyrazolyloxadiazolines , pyrazolylthiadiazolines , imidazolylpyrazoles , pyrazolopyridines , chromenopyrazolones , and thiopyranothiazolylpyrazoles . These are equally important in the field of medicinal as well as pharmaceutical chemistry because of significant biological activities, such as anti‐inflammatory , antioxidant, antibacterial, and antifungal activities .…”

Section: Introductionmentioning

confidence: 99%

Phthaloyl Dichloride–DMF Mediated Synthesis of Benzothiazole‐based 4‐Formylpyrazole Derivatives: Studies on Their Antimicrobial and Antioxidant Activities

Bala

Poonam

Sood

et al. 2018

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).Benzothiazole-based pyrazole derivatives prepared by a molecular hybridization approach with an aim to influence the biological activity significantly. Efficient conversion of hydrazones 3a-k derived from their corresponding methyl ketones to 4-formylpyrazoles 4a-k was carried out at 60°C in dioxane, using the Vilsmeier-Haack reagent isolated from phthaloyl dichloride and N,N-dimethylformamide. The newly synthesized compounds 4a-k and hydrazones 3a-k were screened in vitro for their antimicrobial activities using the broth macrodilution method. The compounds 4a-k were also screened for their antioxidant activities using the DPPH radical scavenging assay. Some of the synthesized compounds showed significant antibacterial and antifungal activities as evident from their minimum inhibitory concentrations. Compound 4d showed remarkable antioxidant activity. J. Heterocyclic Chem., 55, 2507 (2018. Scheme 1. Synthesis of compounds 3a-k and 4a-k. Reagents and conditions: (a) AcOH, MeOH, reflux, 1 h; (b) OPC-VH reagent 6, dioxane, 60°C, 2-5 h. Scheme 2. Synthesis of OPC-VH reagent. Reagents and conditions: (a) 2-Chlorotoluene, 50°C, 3 h.

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“…Nitrogen nucleophiles such as hydrazine, o-Phenylenediamine are important precursor to many heterocylic compounds like pyrazoles [4][5][6] , benzimidazoles 7,8 , quinoxalines 9 ,1,5-benzodiazipine 10,11 etc. Hydrazine finds application in the synthesis of azine derivatives 12 , which have anti-bacterial, anti-fungal and anti-tumour activities 13 .…”

Section: Introductionmentioning

confidence: 99%

Unexpected efficient reactions of nitrogen nucleophiles with α,β-unsaturated nitriles / esters

K¹,

Saravanan²,

Muthusubramanian³

2017

JOAASR

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α,β-Unsaturated compounds containing aldehyde, ketone, nitrile and ester functional groups are versatile precursor for the synthesis of novel organic molecules. All these compounds undergo Michael addition of carbon and other nucleophiles at b-carbon atom of the a,b-unsaturated system. Different carbo- and hetero-cyclic compounds can be synthesized by varying the conditions of cyclisation of the Michael adducts. In this context, it is planned to synthesize pyrazole derivatives and diazepine derivatives by reacting a,b-unsaturated compounds with different Nitrogen nucleophiles such as, o-phenylenediamine etc. The present investigation reports the unexpected hydrogenation of C=C in a,b-unsaturated nitriles and the unexpected synthesis of azine derivatives from a,b-unsaturated nitrileand hydrazinium sulphate.

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Azolylimidazoles: Synthetic strategies and medicinal applications

Abstract: Abstract:The current review summarizes the known routes to different azoles linked directly to imidazole. This review is divided into classes based on the type of azoles connected to an imidazole ring. Some medical applications are mentioned.

Cited by 8 publications

References 13 publications

Design, Docking, Synthesis and Biological Evaluation of Novel Nicotinohydrazone Derivatives as Potential Butyrylcholinesterase Enzyme Inhibitor

Design, Docking, Synthesis and Biological Evaluation of Novel Nicotinohydrazone Derivatives as Potential Butyrylcholinesterase Enzyme Inhibitor

Phthaloyl Dichloride–DMF Mediated Synthesis of Benzothiazole‐based 4‐Formylpyrazole Derivatives: Studies on Their Antimicrobial and Antioxidant Activities

Unexpected efficient reactions of nitrogen nucleophiles with α,β-unsaturated nitriles / esters

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