Room temperature ionic liquids, such as N,N,N-trimethyl-N-(2-hydroxyethyl)ammonium bis(trifluoromethylsulfonyl)imide, [N1 1 1 2(OH)][NTf2] and 1-ethyl-3-methylimidazolium ethylsulfate, [C2mim][C2SO4], have been used for the electroreductive intramolecular cyclization of unsaturated bromo derivatives 1 in Ni(II)-catalyzed reactions. Controlled-potential electrolyses led to five-membered-ring compounds in moderate ...
Radical cyclization continues to be a central methodology for the preparation of natural products containing heterocyclic rings. Hence, some electrochemical results obtained by cyclic voltammetry and controlled-potential electrolysis in the study of electroreductive intramolecular cyclization of ethyl (2S, 3R)-2-bromo-3-propargyloxy-3-(2’,3’,4’,6’-tetra-O-acetyl-beta-D-glucopyranosyloxy) propanoate (1a), 2-brom...
New benzopsoralen analogues were synthesized and their inhibitory effect on the growth of tumourtumour cell lines (MDA MB231 and TCC-SUP) was evaluated. The in vitro antitumour activity of the new benzopsoralen analogues was discussed in terms of structure–activity relationship. Molecular docking studies with human-CYP2A6 enzymes were also carried out with the synthesized compounds to evaluate the potential of ...
Radical cyclization continues to be a central methodology for the preparation of natural products containing heterocyclic rings. The use of electrogenerated nickel(I) complexes as mediators for cathodic intramolecular cyclizations proved to be successful in the formation of carbocyclic products. In this work, the indirect electroreductive intramolecular cyclization of bromoalkoxylated derivatives 1 catalyzed by...
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New tetracyclic benzofurocoumarin (benzopsoralen) analogues were synthesized and their inhibitory effect on the growth of tumor cell lines was evaluated. The human tumor cell lines used were MDA MB231 (breast adenocarcinoma), HeLa (cervix adenocarcinoma) and TCC-SUP (bladder transitional cell carcinoma). The in vitro antitumor activity of the new benzopsoralens was discussed in terms of structure–activity relat...
Mushroom extracts or isolated compounds may be useful in the search of new potent antimicrobial agents. Herein, it is described the synthesis of protected (acetylated) glucuronide derivatives of p-hydroxybenzoic and cinnamic acids, two compounds identified in the medicinal mushroom Ganoderma lucidum. Their antimicrobial and demelanizing activities were evaluated and compared to the parent acids and G. lucidum e...
The synthesis of a series of novel 1,4-disubstituted 1,2,3-triazole compounds bearing a D-glucose derivative and an heteroaromatic system is described. Alkylation of isatin, 3-methyl-carbazole and one tetrahydro-gamma-carboline with propargyl bromide gave their N-propargyl derivatives in good yields. These compounds further reacted with acetylated D-glucose with the azide group in position 1, to give three fina...
The preparation of several alkynyl esters, derived from amino acids, coumarins and an alkynyl derivative of acetylated D-glucose is described. Eight new glycoconjugates containing the 1,2,3-triazole unit were obtained, by a click approach from the above referred alkynyl derivatives with tetracetyl-beta-D-glucosylazide, prepared in situ from alpha-acetobromoglucose.