Departamento de Química Inorgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, 50009 Zaragoza, Spain.
Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, 50009 Zaragoza, Spain.
Dalton Trans. 2023 Jun 13;52(23):7797-7808. doi: 10.1039/d3dt00079f.
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(PPh)]OTf, [ML]OTf (M = Ag, Au) or [Au(CF)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.
炔丙胺与异硫氰酸酯反应，在温和条件下选择性生成亚氨基噻唑啉、氨基噻唑啉或混合噻唑啉-硫脲化合物。已经观察到，仲炔丙胺导致选择性地形成环状 2-氨基-2-噻唑啉衍生物，而伯炔丙胺形成亚氨基噻唑啉。此外，这些环状噻唑啉衍生物可以与过量的异硫氰酸酯进一步反应，生成噻唑啉-硫脲化合物。这些化合物也可以通过炔丙胺与异硫氰酸酯的摩尔比为 1:2 的反应来实现。已经对这些杂环化合物与银和金的配位研究进行了不同的化学计量，并合成了[ML(PPh)]OTf、[ML]OTf（M=Ag，Au）或[Au(CF)L]型的配合物。还对配体和配合物在肺癌细胞中的细胞毒性进行了初步研究，结果表明，尽管配体没有表现出抗癌活性，但它们与金属的配位，特别是银的配位，大大增强了细胞毒性。
