benzofurans and butenolide

Phthalides and α,β-butenolides are two related classes of oxygenated heterocycles with a wide range of biological activities. An innovative strategy to prepare these compounds is based on C-H bond functionalization reactions, in which two simple, unfunctionalized molecules are coupled together with cleavage of a C-H bond and formation of a C-X bond (X=C or heteroatom). This paper reviews the methods for the synthesis of phthalides and α,β-butenolides by C-H bond functionalization from non-halogenated starting materials. Over 30 methods are reported, mostly developed during the past ten years.

Topics: 4-Butyrolactone; Benzofurans; Catalysis; Coordination Complexes; Cycloaddition Reaction; Molecular Structure; Oxidation-Reduction; Transition Elements

The occurrence of two butenolides, menisdaurilide and aquilegiolide, in commercial specimens of Dicentra spectabilis is reported for the first time; a rapid and direct isolation protocol is described. The ability of these lactones to induce apoptosis in human tumour cell lines at 10 microM concentration is also described. The high abundance and apoptosis-inducing activity reported here indicates that these constituents play a more significant role than the hormonal action previously attributed to them.

Topics: 4-Butyrolactone; Antineoplastic Agents, Phytogenic; Apoptosis; Benzofurans; Cell Line, Tumor; Fumariaceae; HT29 Cells; Humans; Jurkat Cells; Phytotherapy; Plant Extracts; Plant Leaves; Plant Stems

Topics: 3',5'-Cyclic-AMP Phosphodiesterases; 3',5'-Cyclic-GMP Phosphodiesterases; 4-(3-Butoxy-4-methoxybenzyl)-2-imidazolidinone; 4-Butyrolactone; Animals; Benzofurans; Benzoin; Cytosol; Furans; Isoenzymes; Myocardium; Phosphodiesterase Inhibitors; Purinones; Rats; Vasodilator Agents