10.1134/S1070363211010208
The research focuses on the synthesis of substituted 4H-[1,3]thiazino[3,2-a]benzimidazol-4-ols using N-tert-butyl-1-aza-1,3-enynes and symmetrically substituted 2-mercaptobenzimidazoles in water-alcohol solutions. The reaction is chemo- and regioselective, yielding a series of fused [1,3]thiazin-4-ols (IVa–IVf) without the need to isolate intermediates. The structures of these compounds were confirmed through 1H and 13C NMR spectroscopy and X-ray diffraction data. The experiments involved the addition of 2-mercaptobenzimidazole to N-tert-butyl-1-aza-1,3-enynes in methanol, sometimes with a DMF admixture, leading to the formation of the desired compounds with high melting points. The presence of water and DMF in methanol facilitated the hydrolysis of the intermediate [1,3]thiazine-4-tert-butylamine to the final [1,3]thiazin-4-ol products. The crystallographic data of one of the compounds, IVa, was deposited at the Cambridge Crystallographic Data Center with the reference number 757744.
10.1021/jm00387a026
This research aimed to investigate the anti-inflammatory activity of substituted 2-[(2,2,2-trifluoroethyl)sulfonyl]-1H-benzimidazoles, a series of compounds with a distinct mechanism from typical cyclooxygenase inhibiting nonsteroidal anti-inflammatory drugs (NSAIDs). The study focused on compounds that showed activity in the rat adjuvant-induced arthritis model but not in the carrageenan paw edema model, suggesting a unique pharmacological profile. The compounds were found to inhibit the release of lysosomal enzymes from neutrophils, indicating a potential anti-inflammatory effect mediated by neutrophil function. Key chemicals used in the synthesis process included various substituted 2-mercaptobenzimidazoles, alkyl iodides, and perfluoroalkyl iodides, along with reagents like m-chloroperoxybenzoic acid for oxidation to sulfones.
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