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Open AccessProceeding Paper

Exploration of New Inhibitors as Anti-Alzheimer Agents Through Molecular Modeling

by Ferdaous Hasni, Ismail Daoud and Nadjib Melkemi

Chem. Proc. 2025, 18(1), 133; https://doi.org/10.3390/ecsoc-29-26898 - 13 Nov 2025

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Alzheimer’s disease (AD) is a neurodegenerative disease that accounts for more than 80% of dementia cases worldwide. This a neurological disorder that encompasses various stages of development (mild, moderate, or severe cognitive impairment), including certain psychological and behavioral syndromes such as depression, psychosis, [...] Read more.

Alzheimer’s disease (AD) is a neurodegenerative disease that accounts for more than 80% of dementia cases worldwide. This a neurological disorder that encompasses various stages of development (mild, moderate, or severe cognitive impairment), including certain psychological and behavioral syndromes such as depression, psychosis, and aggression. The main drug classes currently used to treat AD are acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors. Advancements in bioinformatics and chemometrics have positioned the in silico approach as a pivotal tool in identifying novel therapeutic compounds.Therefore, we conducted a study to evaluate the effects of various newly developed N-substituted 5-chloro-2(3H)-benzoxazolone derivatives on AchE. The aim of this research paper was to utilize in silico ADMET profiling to investigate the potential of natural analogs as inhibitors of AchE, using computational techniques such as swissadme. Analysis of selected ligands with the highest affinity for the target was performed to evaluate ADME properties. The calculation of ADME properties proved that these ligands follow the rules of Lipinski, Veber, and Egan and confirmed the docking results, indicating that they are probably the best inhibitors. Furthermore, they could be utilized to create novel pharmaceutical medicines with which to treat individuals with AD. Full article

(This article belongs to the Proceedings of The 29th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 347 KB

Open AccessShort Note

(E)-5-(3-Oxo-3-(3,4,5-trimethoxyphenyl)prop-1-en-1-yl)benzo[d]oxazol-2(3H)-one

by Yordanka B. Ivanova, Filip E. Svetoslavov and Ognyan I. Petrov

Molbank 2024, 2024(3), M1866; https://doi.org/10.3390/M1866 - 13 Aug 2024

Cited by 1 | Viewed by 1604

Abstract

The title compound, (E)-5-(3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-en-1-yl)benzo[d]oxazol-2(3H)-one, was synthesized by the acid- and base-catalyzed aldol condensation of 2-oxo-2,3-dihydrobenzo[d]oxazole-5-carbaldehyde and 3,4,5-trimethoxyacetophenone. The structure of the target compound was confirmed using ¹H NMR, ¹³C NMR, HRMS, and elemental analysis. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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4 pages, 1078 KB

Open AccessProceeding Paper

Fe-Catalyzed Synthesis of 2-Benzoxazolone—An Important Fragment of Biologically Active Compounds

by Zemfira G. Urazbaeva, Alfiya R. Bayguzina and Ilfir R. Ramazanov

Chem. Proc. 2022, 12(1), 63; https://doi.org/10.3390/ecsoc-26-13564 - 14 Nov 2022

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Abstract

2-Benzoxazolone, as well as its derivatives, are valuable structural fragments of a number of important biologically active substances. 2-Benzoxazolone derivatives are promising as antitumor, antimicrobial, antiretroviral, anticonvulsant, tranquilizing, and insecticidal agents. 2-Benzoxazolone is usually produced by the condensation of o-aminophenol with urea, phosgene, [...] Read more.

2-Benzoxazolone, as well as its derivatives, are valuable structural fragments of a number of important biologically active substances. 2-Benzoxazolone derivatives are promising as antitumor, antimicrobial, antiretroviral, anticonvulsant, tranquilizing, and insecticidal agents. 2-Benzoxazolone is usually produced by the condensation of o-aminophenol with urea, phosgene, and other carbonic acid derivatives. There are also methods for the synthesis of 2-benzoxazolone from salicylamide with trichloroisocyanuric acid as a chlorinating agent, from hydroxybenzoic acid using ammonium azide and the Vilsmeier complex. The disadvantages of these methods are the high cost of the initial reagents, the need to use aggressive and toxic reagents (phosgene, ammonium azide), and the complexity of the hardware design for the reactors. We have developed the highly efficient oxidative cyclocarbonylation of 2-aminophenol to oxazolidin-2-one using FeCl₃*6H₂O and Fe(acac)₃ as catalysts under relatively mild conditions (100–120 °C) in the presence of CCl₄ and water. We assume that in situ-formed carbon dioxide is involved in a cyclization reaction with o-aminophenol to form the target 2-benzoxazole. The reaction takes 2–10 h to give 2-benzoxazolone a high yield. Full article

(This article belongs to the Proceedings of The 26th International Electronic Conference on Synthetic Organic Chemistry)

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9 pages, 2371 KB

Open AccessArticle

Solvent Effects in the Regioselective N-Functionalization of Tautomerizable Heterocycles Catalyzed by Methyl Trifluoromethanesulfonate: A Density Functional Theory Study with Implicit Solvent Model

by Nelson H. Morgon, Srijit Biswas, Surajit Duari and Aguinaldo R. de Souza

Computation 2022, 10(10), 172; https://doi.org/10.3390/computation10100172 - 26 Sep 2022

Cited by 2 | Viewed by 3197

Abstract

Methyl trifluoromethanesulfonate was found to catalyze the reaction of the nucleophilic substitution of the hydroxyl group of alcohols by N-heterocycles followed by X- to N- alkyl group migration (X = O, S) to obtain N-functionalized benzoxazolone, benzothiazolethione, indoline, [...] Read more.

Methyl trifluoromethanesulfonate was found to catalyze the reaction of the nucleophilic substitution of the hydroxyl group of alcohols by N-heterocycles followed by X- to N- alkyl group migration (X = O, S) to obtain N-functionalized benzoxazolone, benzothiazolethione, indoline, benzoimidazolethione and pyridinone derivatives. A high degree of solvent dependency on the yield of the products was observed during optimization of the reaction parameters. The yield of the product was found to be 0%, 48% and 70% in acetonitrile, 1,2-dichloroethane and chloroform, respectively. The mechanism of the reaction was established through experiments as well as DFT calculations. The functional B3LYP and 6-311++G(d) basis function sets were used to optimize the molecular geometries. D3 Grimme empiric dispersion with Becke–Johnson dumping was employed, and harmonic vibrational frequencies were calculated to characterize the stationary points on the potential energy surface. To ensure that all the stationary points were smoothly connected to each other, intrinsic reaction coordinate (IRC) analyses were performed. The influence of solvents was considered using the solvation model based on density (SMD). The free energy profiles of the mechanisms were obtained with vibrational unscaled zero-point vibrational energy (ZPE), thermal, enthalpy, entropic and solvent corrections. Full article

(This article belongs to the Special Issue Calculations in Solution)

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8 pages, 2227 KB

Open AccessArticle

Experimental and Theoretical Investigation on the Thermochemistry of 3-Methyl-2-benzoxazolinone and 6-Nitro-2-benzoxazolinone

by Ana L. R. Silva, Vânia M. S. Costa and Maria D. M. C. Ribeiro da Silva

Molecules 2022, 27(1), 24; https://doi.org/10.3390/molecules27010024 - 21 Dec 2021

Cited by 1 | Viewed by 3811

Abstract

The determination of the reliable thermodynamic properties of 2-benzoxazolinone derivatives is the main goal of this work. Some correlations are established between the energetic properties determined and the structural characteristics of the title compounds, and the reactivity of this class of compounds is [...] Read more.

The determination of the reliable thermodynamic properties of 2-benzoxazolinone derivatives is the main goal of this work. Some correlations are established between the energetic properties determined and the structural characteristics of the title compounds, and the reactivity of this class of compounds is also evaluated. Static-bomb combustion calorimetry and high-temperature Calvet microcalorimetry were used to determine, respectively, the standard molar enthalpies of formation in the solid state and the standard molar enthalpies of sublimation, both at T = 298.15 K. Using the results obtained for each compound, the respective gas-phase standard molar enthalpy of formation was derived. High-level quantum chemical calculations were performed to estimate the same property and the results evidence good accordance. Moreover, the gas-phase relative thermodynamic stability of 2-benzoxazolinone derivatives was also evaluated using the respective gas-phase standard molar Gibbs energy of formation. In addition, the relationship between the energetic and structural characteristics of the benzoxazolinones is presented, evidencing the enthalpic increments associated with the presence of a methyl and a nitro groups in the molecule, and this effect is compared with similar ones in other structurally related compounds. Full article

(This article belongs to the Special Issue Synergies on the Trio Energy-Structure-Reactivity: Nitrogen- containing Heterocyclic Compounds)

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3 pages, 371 KB

Open AccessShort Note

6-[1-Acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-3-yl]-2(3H)-benzoxazolone

by Yordanka Ivanova, Antonya Todorova, Christo Chanev and Ognyan Petrov

Molbank 2018, 2018(4), M1021; https://doi.org/10.3390/M1021 - 30 Sep 2018

Viewed by 2801

Abstract

The title compound, 6-[1-acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl]-2(3H)-benzoxazolone, was synthesized by condensation of 6-[3-(4-methoxyphenyl)-2-propenoyl]-2(3H)-benzoxazolone (1) and hydrazine hydrate in acetic acid in 84% yield. The structure of the target compound was confirmed using ¹H-NMR, ¹³C-NMR, IR, MS, and elemental analysis. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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3 pages, 347 KB

Open AccessShort Note

6-[(4-Chlorophenyl)(1H-1,2,4-triazol-1-yl)methyl]-3-methyl-2(3H)-benzoxazolone

by Mariana S. Gerova, Yordanka B. Ivanova, Christo D. Chanev and Ognyan I. Petrov

Molbank 2016, 2016(2), M901; https://doi.org/10.3390/M901 - 1 Jun 2016

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Abstract

A new hybrid molecule containing a triazole and a benzoxazolone ring was synthesized. The structure of 6-[(4-chlorophenyl)(1H-1,2,4-triazol-1-yl) methyl]-3-methyl-2(3H)-benzoxazolone was confirmed by IR, ¹H-, ¹³C-NMR, MS and elemental analysis. Full article

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15 pages, 753 KB

Open AccessArticle

TDAE Strategy in the Benzoxazolone Series: Synthesis and Reactivity of a New Benzoxazolinonic Anion

by Aïda R. Nadji-Boukrouche, Omar Khoumeri, Thierry Terme, Messaoud Liacha and Patrice Vanelle

Molecules 2015, 20(1), 1262-1276; https://doi.org/10.3390/molecules20011262 - 14 Jan 2015

Cited by 6 | Viewed by 7364

Abstract

We describe an original pathway to produce new 5-substituted 3-methyl-6-nitro-benzoxazolones by the reaction of aromatic carbonyl and α-carbonyl ester derivatives with a benzoxazolinonic anion formed exclusively via the TDAE strategy. Full article

(This article belongs to the Section Organic Chemistry)

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2 pages, 118 KB

Open AccessShort Note

3-(2-Oxopropyl)-2(3H)-benzoxazolone

by Ognyan I. Petrov, Yordanka B. Ivanova, Mariana S. Gerova and Katya V. Petrova

Molbank 2007, 2007(3), M552; https://doi.org/10.3390/M552 - 30 May 2007

Cited by 1 | Viewed by 4002

Abstract

The title compound is an important intermediate for the preparation of 3,4- and 3,4,5-substituted 1-(2-hydroxy-phenyl)imidazolin-2-ones [1,2] and 6-methyl-4-(2-hydroxyphenyl)-1,2,4-triazin-3-ones [3].[...] Full article

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