Synonyms:stannane;tin tetrahydride
The research focuses on the synthesis and biological evaluation of sugar-modified derivatives of cytostatic 6-hetaryl-7-deazapurine nucleosides, specifically 2′-C-methylribonucleosides, arabinonucleosides, and 2′-deoxy-2′-fluoroarabinonucleosides. The purpose of this study was to prepare and investigate the potential cytostatic and antiviral activities of these novel nucleoside analogs, which were synthesized through palladium-catalyzed cross-coupling reactions of protected 6-chloro-(7-fluoro)7-deazapurine nucleosides with various (het)arylboronic acids, stannanes, and trimethylaluminium, followed by deprotection steps. Key intermediates in the synthesis included 6-chloro-7-deazapurine 2′-C-methylβ-D-ribofuranoside and 6-chloro-7-deazapurine arabinofuranoside. Despite the complex synthesis process, none of the prepared compounds exhibited significant cytostatic or antiviral activity, suggesting that the cytostatic activity of 6-hetaryl-7-deazapurine nucleosides is limited to ribonucleosides. The chemicals used in this process included various nucleoside precursors, protecting groups, palladium catalysts, and coupling partners such as (het)arylboronic acids and stannanes.
The study focuses on the total synthesis of Spirastrellolide A Methyl Ester, a complex natural product with potent and selective inhibitory activity against protein phosphatase 2A, which plays a significant role in cellular processes and is implicated in diseases like cancer and Alzheimer's. The synthesis involves the creation of an advanced C17–C40 bis-spiroacetal subunit, a key structural component of Spirastrellolide A, using two complementary strategies: a Julia olefination (Strategy A) and a Suzuki cross-coupling reaction (Strategy B). The chemicals used in the study include a variety of reagents and intermediates such as stannane 4, seco acid 5, alkyne 6, sulfone 8, aldehyde 9, and others, which serve to construct and modify the complex carbon backbone and stereocenters of the target molecule. The purpose of these chemicals is to facilitate the formation of the necessary bonds, rings, and functional groups in a controlled manner to achieve the desired molecular structure, ultimately leading to the first total synthesis of Spirastrellolide A methyl ester.
The research describes the total synthesis of a potent hybrid of the anticancer natural products dictyostatin and discodermolide. The hybrid was designed to have enhanced cell growth inhibitory activity compared to discodermolide, and it was found to retain this potent activity even against the Taxol-resistant NCI/ADR-Res cell line. The synthesis involved a series of chemical reactions, including a cross-coupling–macrolactonisation endgame, a Still–Gennari ole?nation, and a copper-mediated Stille cross-coupling. Key chemicals used in the synthesis include aldehyde 47, b-ketophosphonate 5, lactate-derived ketone 79, aldehyde 8, vinyl iodide 14, stannane 6, and various reagents for reduction, hydrolysis, and protection steps. The resulting hybrid 3 demonstrated low nanomolar cell growth inhibitory activity in vitro against four human cancer cell lines, suggesting its potential as a novel anticancer agent. The study also explored the contribution of the C7,C9-diol to the pharmacophore by synthesizing and testing an acetonide derivative 15, which had significantly reduced cytotoxicity.
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