[3 + 2] Cycloaddition Synthesis of New (Chromene‐1,3,4‐Oxadiazole) Hybrids Linked to Pyrazole Units as Potential Acetylcholinesterase Inhibitors

ChemistrySelect, Год журнала: 2025, Номер 10(2)

Опубликована: Янв. 1, 2025

Abstract A lot of interest has been gained recently in developing novel acetylcholinesterase (AChE) inhibitors that can alleviate Alzheimer's symptoms. In the current study, we aimed to explore AChE inhibitory activity new chromenes attached 1,3,4‐oxadiazole and/or pyrazole units. The hybrids were obtained via [3 + 2] cycloaddition reaction between appropriate chromene‐based enaminones and hydrazonyl chlorides. inhibition percentages products against recorded at tested concentrations 15 25 µM compared donepezil. 3‐(3‐Acetyl‐1‐(4‐methoxyphenyl)‐1 H ‐pyrazole‐4‐carbonyl)‐6‐(((5‐phenyl‐1,3,4‐oxadiazol‐2‐yl)thio)methyl)‐2 ‐chromen‐2‐one displayed promising with 73.2 87.3, respectively, aforementioned concentrations. Moreover, previous hybrid gave 2,2‐diphenylpicrylhydrazyl (DPPH) using reference ascorbic acid. It had an percentage 86.6 a concentration µM.

Язык: Английский

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New thieno[2,3-b]pyridine-fused pyrimidin-4(3H)-ones as potential thymidylate synthase inhibitors: Synthesis, SAR, in vitro and in silico study

Journal of Molecular Structure, Год журнала: 2023, Номер 1282, С. 135236 - 135236

Опубликована: Фев. 26, 2023

Язык: Английский

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One-pot synthesis and antibacterial screening of new (nicotinonitrile-thiazole)-based mono- and bis(Schiff bases) linked to arene units

Synthetic Communications, Год журнала: 2023, Номер 53(3), С. 245 - 261

Опубликована: Янв. 2, 2023

AbstractTwo series of (nicotinonitrile-thiazole)-based Schiff bases 1 and their bis(Schiff bases) analogs 2 are efficiently prepared in this study. A one-pot protocol was designed to prepare the target products involved reaction respective nicotinonitrile-based salicylaldehyde, thiosemicarbazide, appropriate mono- or bis(α-haloketones). The heated at 100 °C for 5–8 h dioxane mediated by triethylamine produce hybrids 80–92% yields. Generally, demonstrated superior antibacterial activity over 2. 1d 1e linked p-tolyl 4-methoxyphenyl units best against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, Pseudomonas aeruginosa strains. They had MIC MBC values ranging from 3.8 4.0 7.7 8.0 µM, respectively. Using SwissADME predict physicochemical properties, lipophilicity, drug-likeness new products, can be considered as drug-like scaffolds. Keywords: Hantzsch thiazole synthesisin vitro screeningmulticomponent reactionsSchiff baseSwissADME

Язык: Английский

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The most Recent Compilation of Reactions of Enaminone Derivatives with various Amine Derivatives to Generate Biologically Active Compounds

Mini-Reviews in Medicinal Chemistry, Год журнала: 2023, Номер 24(8), С. 793 - 843

Опубликована: Сен. 14, 2023

Heterocyclic derivatives serve as the fundamental components of both natural and synthetic drugs. Enaminones play a crucial role foundational units in synthesis numerous bioactive heterocyclic compounds, including pyrazoles, pyridines, oxazoles, isoxazoles, well fused structures like indoles, carbazoles, quinolines, acridines, phenanthridines. These diverse rings are well-known for their various therapeutic activities, encompassing anticancer, anti-inflammatory, antimicrobial, antidepressant, antiviral properties. By reacting with nitrogenbased nucleophiles, enaminones can generate azoles, azines, systems. This study focuses on recent advancements enaminone reactions (a) nitrogen-based such aliphatic amines, aniline, hydroxylamine, hydrazine derivatives, guanidine urea, thiourea (b) electrophiles, diazonium salts. have led to wide range compounds from 2010 end 2022.

Язык: Английский

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Three-component regioselective synthesis and antibacterial evaluation of new arene-linked bis(pyrazolo[1,5-a]pyrimidine) hybrids

Synthetic Communications, Год журнала: 2023, Номер 53(9), С. 658 - 672

Опубликована: Март 22, 2023

In the current study, a three-component protocol was adopted to efficiently synthesize butane-linked bis(pyrazolo[1,5-a]pyrimidines) 1 attached arene units in 74–81% yields. The one-pot reaction involved reacting bis(aldehyde) with respective 1H-pyrazole-3,5-diamines and acetophenones ethanol at 80 °C presence of potassium hydroxide for 6 h. Using similar protocol, another series regioisomeric 2 prepared, 77–87% yields, utilizing appropriate synthons bis(acetyl) benzaldehydes. new products showed wide spectrum antibacterial activity against six different ATCC strains. general, 3-(4-methoxybenzyl) exceeded their analogues 3-(4-chlorobenzyl) activity. Moreover, hybrids which are linked para-electron releasing substituents demonstrated improved hybrid 2h, 7-(4-methoxyphenyl) units, had best all strains tested. It more effective than ciprofloxacin MIC/MBC values up 2.0/4.0 µM.

Язык: Английский

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New Arylazo‐Based (Chromene‐Thiazole) Hybrids as Potential MRSA Inhibitors

Chemistry & Biodiversity, Год журнала: 2023, Номер 20(4)

Опубликована: Март 22, 2023

A three-component protocol was established to efficiently synthesize (chromene-thiazole) and related arylazo analogs in good excellent yields. The desired products were prepared by reacting the appropriate salicylaldehydes, 2-cyanothioacetamide, chloroacetone or hydrazonyl chlorides. Using piperidine as a mediator ethanol at 80 °C for 4-6 h, produce target hybrids 87-96 % newly synthesized showed broad range of antibacterial activity. addition an unit chromene-C6 position significantly improved activity, while impact adding group thiazole-C5 varied based on electronic characteristics para-substituted arene unit. Generally, series that is linked two units, one other thiazole-C5, best Some new effective activity than ciprofloxacin with MIC/MBC values up 1.9/3.9 μM against S. aureus E. coli. Additionally, they demonstrated better effectiveness MRSA ATCC:33591 ATCC:43300 compared linezolid, 4.0/16.1 3.9/15.6 μM, respectively. data predicted physicochemical properties, lipophilicity, pharmacokinetics, drug-likeness arylazo-based chromene-thiazole evaluated SwissADME. As result above, are units can be considered drug-like scaffolds.

Язык: Английский

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Bis(ethanones) and their derivatives: Versatile precursors for bis(heterocycles)

Advances in heterocyclic chemistry, Год журнала: 2023, Номер unknown, С. 227 - 276

Опубликована: Дек. 14, 2023

Язык: Английский

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