N,N -Disubstituted Aminomethyl Benzofuran Derivatives: Synthesis and Preliminary Binding Evaluation

Antioxidant activity of benzoxazolinonic and benzothiazolinonic derivatives in the LDL oxidation model

“…The formyl derivative 6 was condensed with nitromethane in the presence of a catalytic amount of ammonium acetate to afford the expected nitrovinyl product 7 by a Henry reaction. 28,29 Reduction of the a,b-unsaturated nitroalkene 7 to the desired saturated compound 5b was performed with sodium borohydride in a mixture of chloroform and isopropanol in the presence of silica gel, followed by hydrogenation over Pd/C. This way gave low yield of 29% while compound 5b was obtained using the first way in three steps with 47% yield.…”

Short and Efficient Route to the Fully Functionalized Polar Core of Scyphostatin

“…This left us with the challenge of controlling the stereochemistry of 4 , hopefully by diastereoselective oxidative dearomatization 8 of benzopyran 5 . Such benzopyranes can be easily prepared from 2,4-dihydroxybenzaldehyde ( 6 ) 2 Retrosynthetic Plan for Scyphostatin's Polar Core a a PIFA = [bis(trifluoroacetoxy)iodo]benzene. …”

“…Thus, the required aminobenzopyrane 8a (R 1 = Bn, Scheme ) was easily prepared, in analogy with the known aminobenzopyrane 8b (R 1 = Me), in three steps and 61% overall yield from 4-benzyloxy-2-hydroxy-benzaldehyde ( 7 ) . To explore the feasibility of our strategy, we chose palmitic acid as a surrogate for the fatty side chain of scyphostatin and decided to utilize racemic aminobenzopyrane 8a .…”

Synthesis and Biological Activity of New Melatonin Receptor Ligands

“…In our continuing study of heterocyclic compounds with potential biological activity (Savelon et al 1998;Boye  et al 1999), we present here initial results on the design of new non-indole melatoninlike compounds in which the amide group has a carbon-nitrogen sequence (Leclerc et al 1998), in contrast with that of melatonin in which the order is opposite (nitrogen-carbon). The aim of this study was to evaluate for three ®xed skeletonsÐ1,4benzodioxin, 2,3-dihydro-1,4-benzodioxin and 2,3dihydro-1,4-benzoxathiinÐthe importance of the length of the retroamide side-chain in the interaction of the molecule when binding to, and acting on, the melatonin receptor.…”