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1.
J Org Chem ; 89(8): 5353-5362, 2024 Apr 19.
Artículo en Inglés | MEDLINE | ID: mdl-38564378

RESUMEN

Catalyst-free Markovnikov-selective hydrothiolation of unactivated alkenes still remains a great challenge. Herein, we develop a catalyst/metal/solvent-free methodology for the Markovnikov hydrothiolation of unactivated alkenes with in situ prepared dithiocarbamic acids, providing a wide array of alkyl dithiocarbamates. A variety of terminal, internal, cyclic, and acyclic unactivated alkenes were applied successfully in this protocol. This three-component thiol-ene reaction can be considered as a new family of click reactions.

2.
Beilstein J Org Chem ; 20: 1462-1467, 2024.
Artículo en Inglés | MEDLINE | ID: mdl-38978745

RESUMEN

Herein, we report the first environmentally friendly systematic fluoroalkoxylation reactions in bicyclic systems. New oxyfluorination products were obtained with excellent yields (up to 98%) via Wagner-Meerwein rearrangement using benzonorbornadiene and the chiral natural compound (+)-camphene as bicyclic alkenes, selectfluor as an electrophilic fluorine source, and water and various alcohols as nucleophile sources. The structure of bicyclic oxy- and alkoxyfluorine compounds was determined by NMR and QTOF-MS analyses.

3.
Chem Biodivers ; 20(1): e202200509, 2023 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-36514919

RESUMEN

Salicylic acid is an NSAID with serious side effects on the GIS. The side effects of salicylic acid on the GIS are slightly reduced by acetylating salicylic acid. 12 new ester analogs of salicylic acid were synthesized with high yields in this study. The chemical structures of the synthesized compounds were characterized by 1 H-NMR, 13 C-NMR, and HRMS spectra. The inhibitory potential of the compounds was evaluated on COXs by in vitro and in silico studies. The COX2 inhibitory activity of the most potent inhibitor MEST1 (IC50 : 0.048 µM) was found to be much higher than the COX2 inhibitory activity of aspirin (IC50 : 2.60 µM). In docking studies, the strongest inhibitor among the compounds synthesized was predicted to be MEST1, with the lowest binding energy. Docking studies revealed that MEST1 extends from the hydrophobic channel to the top of the cyclooxygenase active site, forming various interactions with residues in the binding pocket.


Asunto(s)
Inhibidores de la Ciclooxigenasa 2 , Ácido Salicílico , Inhibidores de la Ciclooxigenasa 2/química , Ácido Salicílico/farmacología , Ésteres/farmacología , Simulación del Acoplamiento Molecular , Antiinflamatorios no Esteroideos/farmacología , Ciclooxigenasa 2/metabolismo , Relación Estructura-Actividad , Estructura Molecular
4.
Chem Biodivers ; 19(6): e202200015, 2022 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-35470963

RESUMEN

The major cholinesterase enzymes, acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), are important in the therapy of Alzheimer's disease (AD) based on the cholinergic hypothesis. As a result, in recent years, the investigation of dual cholinesterase inhibition methods has become important among scientists. In this study, novel N-(4-chlorobenzyl)-3,4-dimethoxy-N-(m-substituted)benzamide derivatives were synthesized. Then, inhibitory properties of these derivatives were examined in human AChE and BuChE in vitro and possible interactions were determined by molecular docking studies. All benzamide derivatives were exhibited dual inhibitory character and high BBB permeability. The most effective inhibitor was found as N7 for both AChE and BuChE with IC50 values of 1.57 and 2.85 µM, respectively. Besides the most potent inhibitor was predicted as N7 in terms of binding energies with -12.18 kcal/mol and -9.92 kcal/mol, respectively. The reason for these results is that bromine (N7) is the bulkiest molecule among the other substituted groups. These derivatives could be exploited to develop new medications for the treatment of central nervous system-related diseases as AD by acting as dual inhibitors of AChE and BChE.


Asunto(s)
Enfermedad de Alzheimer , Inhibidores de la Colinesterasa , Acetilcolinesterasa/metabolismo , Enfermedad de Alzheimer/tratamiento farmacológico , Benzamidas , Butirilcolinesterasa/metabolismo , Inhibidores de la Colinesterasa/química , Humanos , Simulación del Acoplamiento Molecular , Estructura Molecular , Relación Estructura-Actividad
5.
Artículo en Inglés | MEDLINE | ID: mdl-38497359

RESUMEN

Many disorders, including cancer and malaria, could be targeted via the pentose phosphate pathway (PPP), whose products are key in biosynthetic reactions in cells. The goal of this study was to find new PPP inhibitors. The inhibition effects of malononitrile derivatives on Glucose 6-phosphate dehydrogenase (G6PD) and 6-phosphogluconate dehydrogenase (6PGD) were analyzed through in vitro experiments. Besides, molecular docking studies were performed to predict the interactions having role in inhibition of compounds. K i constants of derivatives were found between 4.24 ± 0.46-69.63 ± 7.75 µM for G6PD and 1.91 ± 0.12-95.07 ± 11.08 µM for 6PGD. Derivatives indicated non-competitive inhibition on both enzymes except for compound 4. The findings of the molecular docking studies revealed that free-binding energy estimations agreed with in vitro data. The structure of these malononitrile derivatives may guide for drug discovery in targeting the PPP.

6.
Org Lett ; 24(45): 8261-8264, 2022 Nov 18.
Artículo en Inglés | MEDLINE | ID: mdl-36129307

RESUMEN

Herein, we report the first metal-free and molecular halogen reagent-free dihomohalogenation methodology by using Selectfluor as an oxidant and tetrabutylammonium bromide/chloride salts as a halogen source. This effective strategy provides various fluorine-free halogenated products easily in quantitative yields from alkenes, alkynes, and natural products.

7.
Beilstein J Org Chem ; 5: 39, 2009 Aug 11.
Artículo en Inglés | MEDLINE | ID: mdl-19777139

RESUMEN

Dimeric forms of norbornadiene and benzonorbornadiene were synthesized starting with known monobromide derivatives. The Diels-Alder cycloaddition reaction of dimers with TCNE and PTAD was investigated and new norbornenoid polycyclics were obtained. All compounds were characterized properly using NMR spectroscopy.

8.
Chem Commun (Camb) ; 53(92): 12418-12421, 2017 Nov 16.
Artículo en Inglés | MEDLINE | ID: mdl-29052684

RESUMEN

ML2 type complexes of an olefin terminated 5H-dipyrrin ligand can be subjected to twofold ring closing metathesis to give bis(dipyrrinato)copper(ii) and bis(dipyrrinato)zinc(ii) [2]catenates. Demetalation of the copper(ii) [2]catenate with KCN/N2H4·H2O gave the corresponding bis(dipyrrin) [2]catenand. The boron difluoride complex of this bis(dipyrrin) was obtained as the first fluorescent F-BODIPY [2]catenane.

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