Catalysis-free synthesis of thiazolidine–thiourea ligands for metal coordination (Au and Ag) and preliminary cytotoxic studies

Salvador-Gil, Daniel ; P. Herrera, Raquel ; Gimeno, M. Concepción

Resumen: The reaction of propargylamines with isothiocyanates results in the selective formation of iminothiazolidines, aminothiazolines or mixed thiazolidine–thiourea compounds under mild conditions. It has been observed that secondary propargylamines lead to the selective formation of cyclic 2-amino-2-thiazoline derivatives, while primary propargylamines form iminothiazoline species. In addition, these cyclic thiazoline derivatives can further react with an excess of isothiocyanate to give rise to thiazolidine–thiourea compounds. These species can also be achieved by reaction of propargylamines with isothiocynates in a molar ratio of 1 : 2. Coordination studies of these heterocyclic species towards silver and gold with different stoichiometries have been carried out and complexes of the type [ML(PPh3)]OTf, [ML2]OTf (M = Ag, Au) or [Au(C6F5)L] have been synthesised. Preliminary studies of the cytotoxic activity in lung cancer cells have also been performed in both ligands and complexes, showing that although the ligands do not exhibit anticancer activity, their coordination to metals, especially silver, greatly enhances the cytotoxic activity.

Idioma: Inglés

DOI: 10.1039/d3dt00079f

Año: 2023

Publicado en: Dalton Transactions 23, 52 (2023), 7797-7808
ISSN: 1477-9226

Factor impacto JCR: 3.5 (2023)

Categ. JCR: CHEMISTRY, INORGANIC & NUCLEAR rank: 13 / 44 = 0.295 (2023) - Q2 - T1

Factor impacto SCIMAGO: 0.697 - Inorganic Chemistry (Q1)

Financiación: info:eu-repo/grantAgreement/ES/AEI/PID2019-104379RB-C21
Financiación: info:eu-repo/grantAgreement/ES/AEI/PID2020-117455GB-I00
Financiación: info:eu-repo/grantAgreement/ES/DGA-FSE/E07-20R
Financiación: info:eu-repo/grantAgreement/ES/MICINN-AEI/RED2018-102471-T

Tipo y forma: Artículo (Versión definitiva)