Design of pincer complexes based on (methylsulfanyl)acetic/propionic acid amides with ancillary S‐ and N‐donors as potential catalysts and cytotoxic agents |
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Authors: | Svetlana G Churusova Diana V Aleksanyan Andrei A Vasil'ev Ekaterina Yu Rybalkina Olga Yu Susova Zinaida S Klemenkova Rinat R Aysin Yulia V Nelyubina Vladimir A Kozlov |
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Institution: | 1. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia;2. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia;3. Blokhin Russian Cancer Research Center, Institute of Carcinogenesis, Moscow, Russia;4. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow, Russia |
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Abstract: | Pincer complexes featuring readily tunable tridentate ligand frameworks comprise one of the most actively studied classes of organometallic and metal–organic compounds and find extensive use in catalysis, organic synthesis, materials science, and other fields of chemistry and allied disciplines. Currently growing attention is devoted to non‐classical ligand scaffolds, such as functionalized carboxamides, which offer multiple options for directed structural modifications. In this study, the reactions of (methylsulfanyl)acetyl and propanoyl chlorides with 2‐(aminomethyl)pyridine, 2‐(2‐aminoethyl)pyridine, 8‐aminoquinoline and 2‐(diphenylthiophosphoryl)aniline afford a series of new pincer‐type ligands based on functionalized carboxamides. The ligands obtained readily undergo direct cyclopalladation under the action of PdCl2(NCPh)2 in dichloromethane at room temperature, resulting in Pd(II) pincer complexes with N,N,S‐ and S,N,S‐donor sets. Importantly, some of the cyclopalladated derivatives can also be produced efficiently under solvent‐free conditions according to the approach recently developed by our group. The complexes obtained have been tested for cytotoxicity against several human cancer cell lines and catalytic activity in the model Suzuki reaction. The results have been compared to those for the related Pd(II) pincer complexes to define the main structure–activity relationships and to outline the most promising structures for further investigations. |
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Keywords: | carboxamides catalytic activity cytotoxicity pincer complexes solid‐phase synthesis |
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