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1.
Bioorg Med Chem ; 107: 117756, 2024 Jun 01.
Artigo em Inglês | MEDLINE | ID: mdl-38759255

RESUMO

Herein, four silver(I) complexes bearing acetylated d-galactopyranoside-based N-heterocyclic carbene ligands were synthesized and fully characterized by elemental analysis, NMR, and X-ray photoelectron spectroscopy. All complexes were obtained with an anomeric ß-configuration and as monocarbene species. In this study, we investigated the biological effects of the silver(I) complexes 2a-d on the human rhabdomyosarcoma cell line, RD. Our results show concentration-dependent effects on cell density, growth inhibition, and activation of key signaling pathways such as Akt 1/2, ERK 1/2, and p38-MAPK, indicating their potential as anticancer agents. Notably, at 35.5 µM, the complexes induced mitochondrial network disruption, as observed with 2b and 2c, whereas with 2a, this disruption was accompanied by nuclear content release. These results provide insight into the utility of carbohydrate incorporated NHC complexes of silver(I) as new agents in cancer therapy.


Assuntos
Antineoplásicos , Proliferação de Células , Ensaios de Seleção de Medicamentos Antitumorais , Rabdomiossarcoma , Prata , Humanos , Acetilação , Antineoplásicos/farmacologia , Antineoplásicos/química , Antineoplásicos/síntese química , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Complexos de Coordenação/farmacologia , Complexos de Coordenação/química , Complexos de Coordenação/síntese química , Relação Dose-Resposta a Droga , Galactose/química , Galactose/farmacologia , Compostos Heterocíclicos/química , Compostos Heterocíclicos/farmacologia , Compostos Heterocíclicos/síntese química , Metano/química , Metano/análogos & derivados , Metano/farmacologia , Metano/síntese química , Estrutura Molecular , Rabdomiossarcoma/tratamento farmacológico , Rabdomiossarcoma/patologia , Prata/química , Prata/farmacologia , Relação Estrutura-Atividade
2.
RSC Adv ; 14(3): 1626-1633, 2024 Jan 03.
Artigo em Inglês | MEDLINE | ID: mdl-38179092

RESUMO

Following a rational design, three novel palladium(ii) complexes bearing galactopyranoside-based N-heterocyclic carbene ligands have been synthesized via transmetalation of the corresponding Ag(i) complexes. Palladium(ii) complexes have been characterized by NMR, FT-IR and elemental analysis. Catalytic studies, using the Stille and Suzuki-Miyaura cross-coupling reactions as model C-C coupling, reveal that the complexes are active and reusable. The best results in terms of TON values were achieved in aqueous medium using either the in situ deacetylation of the catalyst or the previously deacetylated catalyst. The catalytic condition using in situ deacetylation was more efficient because it avoids an additional deprotection step.

3.
RSC Adv ; 13(39): 27491-27500, 2023 Sep 08.
Artigo em Inglês | MEDLINE | ID: mdl-37711379

RESUMO

Our study unveils an innovative methodology that merges catechols with mono- and disaccharides, yielding a diverse array of compounds. This strategic fusion achieves robust yields and introduces ligands with a dual nature: encompassing both the chelating attributes of catechols and the recognition capabilities of carbohydrates. This synergistic design led us to couple one of the novel ligands with an Fe(iii) salt, resulting in the creation of Coordination Glycopolymer Particles (CGPs). These CGPs demonstrate remarkable qualities, boasting outstanding dispersion in both aqueous media and Phosphate Buffered Saline (PBS) solution (pH ∼7.4) at higher concentrations (0.26 mg µL-1). Displaying an average Z-size of approximately 55 nm and favourable polydispersity indices (<0.25), these particles exhibit exceptional stability, maintaining their integrity over prolonged periods and temperature variations. Notably, they retain their superior dispersion and stability even when subjected to freezing or heating to 40 °C, making them exceptionally viable for driving biological assays. In contrast to established methods for synthesizing grafted glycopolymers, where typically a glycopolymer is doped with catechol derivatives to create synergy between chelating properties and those inherent to the saccharide, our approach provides a more efficient and versatile pathway for generating CGPs. This involves combining catechols and carbohydrates within a single molecule, enabling the fine-tuning of organic structure from a monomer design step and subsequently transferring these properties to the polymer.

4.
ACS Omega ; 7(25): 21788-21799, 2022 Jun 28.
Artigo em Inglês | MEDLINE | ID: mdl-35785281

RESUMO

A series of novel gold(I) complexes bearing galactopyranoside-based N-heterocyclic carbene ligands have been synthesized via transmetalation of the corresponding Ag(I) complex. Gold(I) complexes have been characterized by NMR, Fourier transform infrared (FTIR), and elemental analysis. An exhaustive NMR analysis shows that the complexes are not stable when hydroxyl groups are deprotected. Catalytic studies, using the alkyne hydration as a model reaction, indicate that the synthesized complexes are active and reusable.

5.
Ultrason Sonochem ; 80: 105834, 2021 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-34814046

RESUMO

In organic and inorganic synthesis and in analytical methods, an external conventional heat source is usually applied to carry out a chemical reaction at a high temperature, or an extraction procedure. In the last decades, the use of ultrasound as an alternative energy source has become an interesting field of research in these topics in the South Cone region (Argentina, Chile, Uruguay, Southern Brazil and Paraguay). For this reason, the present review, covering the period 2009 to mid-2021, is a compilation of ultrasound-assisted synthetic and analytical methodologies.

6.
Ultrason Sonochem ; 20(3): 826-32, 2013 May.
Artigo em Inglês | MEDLINE | ID: mdl-23219615

RESUMO

The solvent-free indium-promoted reaction of alkanoyl chlorides with sterically and electronically diverse arylstannanes is a simple and direct method for the regioselective synthesis of primary, secondary and tertiary alkyl aryl ketones in good to excellent isolated yields (42-84%) under mild and neutral conditions. The protocol is also adequate for the synthesis of aryl vinyl ketones. Reaction times are drastically reduced (from 3-32h to 10-70min) under ultrasonic irradiation. Evidences for the involvement of a homolytic aromatic ipso-substitution mechanism, in which indium metal acts as radical initiator, are presented. It is possible the transference of two aryl groups from tin, thus improving effective mass yield, working with diarylstannanes as starting substrates.


Assuntos
Índio/química , Cetonas/síntese química , Sonicação , Compostos de Estanho/química , Catálise , Hidrocarbonetos Clorados/química , Cetonas/química , Cetonas/efeitos da radiação , Estrutura Molecular , Som , Compostos de Estanho/efeitos da radiação
7.
J Org Chem ; 76(6): 1707-14, 2011 Mar 18.
Artigo em Inglês | MEDLINE | ID: mdl-21338129

RESUMO

Bulky arylstannanes and bulky aroyl chlorides are good reaction partners for the synthesis of two-, three-, and even four-ortho-substituted benzophenones, in good to excellent isolated yields (47-91%). Three simple and direct routes, with differential advantages, are proposed: (i) a catalyst-free protocol, in o-dichlorobenzene (ODCB) at 180 °C; (ii) a room temperature protocol, using AlCl(3) (0.5 equiv), in dichloromethane (DCM); and (iii) a solvent-free, indium-promoted procedure. A radical mechanism is proposed for the indium-mediated reactions.


Assuntos
Cetonas/química , Cetonas/síntese química , Compostos de Estanho/química , Catálise , Clorobenzenos/química , Indicadores e Reagentes/química , Índio/química , Especificidade por Substrato
8.
J Org Chem ; 73(22): 9184-7, 2008 Nov 21.
Artigo em Inglês | MEDLINE | ID: mdl-18950227

RESUMO

The exceptional leaving group ability of the trimethylstannyl group in electrophilic aromatic substitutions makes possible the synthesis, in a single step, of bi- and triaroylarenes through the catalyst-free, regioselective reaction of bi- and tristannylarenes with different aroyl halides in o-dichlorobenzene as solvent. Specific di- and triketones are obtained in good to excellent yields (45-83%).


Assuntos
Hidrocarbonetos Policíclicos Aromáticos/química , Catálise , Halogênios/química , Compostos de Estanho/química
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