One-Pot Synthesis of Benzo[b]furan and Indole Inhibitors of Tubulin Polymerization

Abstract

Benzo[b]furan and indole analogues of some recently identified benzo[b]thiophene inhibitors of tubulin polymerization have been prepared, and their biological activity has been assessed. Several very potent analogues were identified.

Synthesis and Evaluation of Antioxidant Activity of Some New Heterocyclic Compounds Bearing the Benzo[B]Furan Moiety

“…Thus the reaction of 2 with benzene diazonium chloride gave the hydrazone derivative 2-[2-(1-(5-methoxy-2-methylbenzofuran-3-yl)ethylidene)hydrazinyl]-2-oxo-Nphenylacetohydrazonoyl cyanide (8). The analytical and spectral data of the product is in consistent with the proposed structure.…”

A microwave-assisted multicomponent protocol for the synthesis of benzofuran-2-carboxamides

“…4 Drugs containing benzofuran rings are in clinical use for the treatment of cardiac arrhythmyas (Amiodarone, Dronedarone), urinary incontinence (Darifenacin), moderate Alzheimer disease (Galantamine), opioids overdose (Naloxone, Naltrexone), tubercolosis infections (Rifampicin, Rifapentin, Rifabutin), hypertension and heart failure (Saprisartan), jet-lag syndrome (Ramelteon). 3 Benzofurans are reported active as plant growth regulators, 5 insecticides, 6 herbicides, 7 anti-inflammatory, 8 anticancer, 9 antifungi, 10 antibacterial, 11 antimalarial 12 and antiviral agents, 13 GPCRs-targeting ligands, like Vilazodone (5-HT 1A partial agonist) and antagonists on Endothelin (1), 19 H 3 (2), 20 Melatonin (3), 21 Neurokinin-1 (4) 22 and Adenosine A 2A receptors ( A fast, versatile and practical microwave-assisted multicomponent protocol for the synthesis of substituted benzofuran-2-carboxamides has been developed. The present method proved to be effective on a series of commercially available amines, 2'-hydroxyacetophenones, aldehydes and benzonitriles and could be exploited in drug-discovery campaigns for the rapid identification of biologically active hit compounds.…”

Synthesis and Antibacterial Activity Study of C-3 α, β-Unsaturated Ketone Linked Benzofuran Derivatives

“…Substitution of the double bond linker with furan moiety is an effective method of structural modification in designing new derivatives from natural oligostilbene [1][2][3][4]. For example, natural product corsifuran C, a furan-substituted oligostilbene analogue bearing 4-methoxyphenyl group at the C-2′ position ( Figure 1) was reported as a neuron-protective and anti-tumor agent.…”

“…It is presumed that the C-3 position of benzofuran ring was a potential functional site, and the single or double hydroxyl substituted phenyl and mathanone linker on C-3 position were essential for antibacterial activity of benzofuran families. Meanwhile, it was noticed that introducing electron-rich groups into the leading compound is a conventional way of molecular structural modification, and may result better biological performance, for example, the ethylene group in Combrestastatin A-4 derivatives [1,3,4] and Chalcone family analogues [10][11][12][13][14][15][16][17]. To examine the effect of antibacterial activities induced by C-3′ linkers, we achieved a further structural modification on C-2 methoxyphenyl substituted benzofuran skeleton by introducing substituted phenyl groups through α, β-unsaturated ketone linker at the C-3′ position in this paper.…”