Synthesis of 3-arylbenzo[1,4]dioxin-2-carboxamides by palladium-catalysed coupling of vinylstannanes with aryl halides

New Substituted 1,4-Benzoxazine Derivatives with Potential Intracellular Calcium Activity

“…Recently a new series of 1,4-benzoxazine derivatives (I) (Chart 1) possessing (4-phenyl-1-piperazinyl)alkyl moieties at the C-2 position of the oxazine ring 40 was synthesized and tested for calcium antagonistic, calmodulin antagonistic, and antihypertensive activities; for example compound I (R 1 ) 6,7-(CH 2 ) 4 -, R 2 ) 4-F, R 3 ) H, n = 3) has shown calmodulin antagonist activity (IC 50 ) 0.52 µM) (racemic or enantiomeric compounds have a similar activity). In connection with our interest in benzodioxine [41][42][43] and benzoxazine [44][45][46] chemistry, we have conceived a new set of 1,4-benzoxazine derivatives, divided in two structural models. The first (derivatives 1-4), in which the 1,4-benzoxazin-3-one skeleton has been replaced by a benzoxazine framework, has allowed us to explore, among others things, the influence of amine Y and the chain length (n) (Chart 2).…”

“…The first (derivatives 1-4), in which the 1,4-benzoxazin-3-one skeleton has been replaced by a benzoxazine framework, has allowed us to explore, among others things, the influence of amine Y and the chain length (n) (Chart 2). The second model (derivatives 5) was based on the introduction of a benzodioxane entity, which has already showed promising activities in our laboratory [41][42][43] (Chart 2). Herein we report the synthesis of these series of compounds and their pharmacological evaluation as potential intracellular calcium antagonists.…”