Metalations utilizing aryllithiums; ortho-functionalization of p-bromoanisole (pBrA)
An ortho-metalation protocol has been developed, which permits the survival of a bromine substituent in p-bromoanisole. Eight derivatives of the generated ortho-lithiated intermediate have been prepared. A neglected metalation concept is being explored here; one which proposes that minimizing the pKa difference between the aryl substrate and the conjugate acid of the metalating agent will lead to a regiospecific and selective metalation process.
Slocum,Reece, Troy L.,Sandlin, Rebecca D.,Reinscheld, Thomas K.,Whitley, Paul E.
experimental part
p. 1593 - 1595
(2009/06/18)
Cationic chalcone antibiotics. Design, synthesis, and mechanism of action
This paper describes how the introduction of "cationic" aliphatic amino groups in the chalcone scaffold results in potent antibacterial compounds. It is shown that the most favorable position for the aliphatic amino group is the 2-position of the B-ring, in particular in combination with a lipophilic substituent in the 5-position of the B-ring. We demonstrate that the compounds act by unselective disruption of cell membranes. Introduction of an additional aliphatic amino group in the á-ring results in compounds that are selective for bacterial membranes combined with a high antibacterial activity against both Gram-positive and -negative pathogens. The most potent compound in this study (78) has an MIC value of 2 μM against methicillin resistant Staphylococus aureus.
Nielsen, Simon F.,Larsen, Mogens,Boesen, Thomas,Sch?nning, Kristian,Kromann, Hasse
p. 2667 - 2677
(2007/10/03)
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