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ChemInform Abstract: Cobalt-Catalyzed Cross-Coupling of Alkynyl Grignard Reagents with Alkenyl Triflates
Abstract
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... Compound 9 was then protected as a Bocsulfonamide by treatment with di-(tert-butyl)dicarbonate in CH 2 Cl 2 using 4- (dimethylamino)pyridine (DMAP) as acylation catalyst [22]. The N-protected intermediate 10 was submitted to the Sonogashira reaction [23,24] in the presence of Pd(II), CuI, triphenylphosphine and triethylamine to afford the acetylenic derivative 11. Acid hydrolysis with TFA allowed to deprotect the carboxylic acid and the sulfonamidic nitrogen in a single step. ...
Matrix metalloproteinases (MMPs) are important factors in gliomas since these enzymes facilitate invasion into the surrounding brain and participate in neovascularization. In particular, the gelatinases (MMP-2 and MMP-9), and more recently MMP-25, have been shown to be highly expressed in gliomas and have been associated with disease progression. Thus, inhibition of these MMPs may represent a promising non-cytotoxic approach to glioma treatment. We report herein the synthesis and biological evaluation of a series of 4-butylphenyl(ethynylthiophene)sulfonamido-based hydroxamates. Among the new compounds tested, a promising derivative, 5a, was identified, which exhibits nanomolar inhibition of MMP-2, MMP-9, and MMP-25, but weak inhibitory activity toward other members of the MMP family. This compound also exhibited anti-invasive activity of U87MG glioblastoma cells at nanomolar concentrations, without affecting cell viability.
Alkenyl triflates in combination with Co(acac)(3) as a catalyst were found to be excellent coupling partners of alkynyl Grignard reagents, where no special additives (even a phosphine ligand) but a common solvent, THF, are required to obtain variously substituted enynes.