benzofurans and coumarin

The favorability of ring closure reactions as per Baldwin rules has gained immense importance recently. This is evident from the current literature such as research articles, reviews, and books that have been published in this area. This review covers the recent applications of 5-endo-dig cyclization in organic synthesis focusing in the last two decades. A variety of 5-membered heterocycles as well as carbocycles could be synthesized via 5-endo-dig cyclization reactions. The important applications of 5-endo-dig cyclization in organic synthesis covering different aspects have been summarized in this review.

Topics: Benzofurans; Catalysis; Chemistry Techniques, Synthetic; Coumarins; Cyclization; Indoles; Molecular Structure

Grapefruit juice (GFJ) consumption has been shown to increase the bioavailability of certain orally administered drugs. The furanocoumarin derivatives Paradisin A and bergamottin, which are present in GFJ, are potent mechanism-based inhibitors of CYP3A4. The primary aim of this work was to synthesize a series of furanocoumarin derivatives with a view to determining the relationship between the structure of the inhibitors and their inhibitory CYP3A4 activity. Furanocoumarin derivatives that were more stable and accessible than the furanocoumarin derivatives in GFJ were prepared, and their ability to inhibit CYP3A4 was examined. Synthesized furanocoumarin monomers showed strong mechanism-based inhibition of CYP3A4. The furanocoumarin dimers are also mechanism-based inhibitors of CYP3A4. These monomers and dimers are more potent inhibitors of CYP3A4 than bergamottin and Paradisin A, respectively.

Topics: Benzofurans; Citrus paradisi; Coumarins; Cytochrome P-450 CYP3A Inhibitors; Fruit and Vegetable Juices; Furocoumarins; Humans; Structure-Activity Relationship

This study identified three coumarins (

Topics: Benzofurans; Chemical Fractionation; Coumarins; Epoxide Hydrolases; Models, Molecular; Molecular Conformation; Molecular Structure; Morus; Plant Leaves

Alzheimer's disease (AD), the most common cause of dementia, is a neurodegenerative disorder characterized by progressive deterioration of memory and cognition. The evidenced multifactorial nature of AD has been considered the main reason for the absence of cure so far. Therefore, the development of novel hybrids to treat the disease is very much essential. Focusing on this, a novel series of coumarin-benzofuran hybrids have been designed and screened as anti-Alzheimer's disease agents. The strategy is to obtain an effective mimetic of donepezil, which is acetylcholinesterase inhibitor. Herein, the two main scaffolds namely coumarin and benzofuran are known pharmacophore moieties and we have performed their molecular design, pharmacokinetic descriptor studies for drug-likeliness. Further, in vitro studies such as antioxidant capacity, acetylcholinesterase (AChE) inhibition and amyloid-β (Aβ) self-aggregation inhibition have also been performed. Most importantly, these studies revealed that the newly synthesized hybrids can be versatile and promising drug-like moieties as efficient anti-AD agents.

Topics: Alzheimer Disease; Amyloid beta-Peptides; Benzofurans; Binding Sites; Cholinesterase Inhibitors; Coumarins; Donepezil; Drug Design; Humans; Molecular Docking Simulation; Peptide Fragments; Structure-Activity Relationship

Coumestan is a natural tetracycle with a C═C bond shared by a coumarin moiety and a benzofuran moiety. In addition to the function of the hydroxyl group on the antioxidant activity of coumestan, it is worth exploring the influence of the oxygen-abundant scaffold on the antioxidant activity as well. In this work, seven coumestans containing electron-withdrawing and electron-donating groups were synthesized to evaluate the abilities to trap 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(•+)), 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively, and to inhibit the oxidations of DNA mediated by (•)OH, Cu(2+)/glutathione (GSH), and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH), respectively. It was found that all of the coumestans used herein can quench the aforementioned radicals and can inhibit (•)OH-, Cu(2+)/GSH-, and AAPH-induced oxidations of DNA. In particular, substituent-free coumestan exhibits higher ability to quench DPPH and to inhibit AAPH-induced oxidation of DNA than Trolox. In addition, nonsubstituted coumestan shows a similar ability to inhibit (•)OH- and Cu(2+)/GSH-induced oxidations of DNA relative to that of Trolox. The antioxidant effectiveness of the coumestan can be attributed to the lactone in the coumarin moiety and, therefore, a hydroxyl group may not be a necessary functional group for coumestan to be an antioxidant.

Topics: Amidines; Antioxidants; Benzofurans; Biphenyl Compounds; Coumarins; DNA; Glutathione; Hydroxyl Radical; Oxidation-Reduction; Picrates

Human microsomal cytochrome P450 (CYP) 2A6 contributes extensively to nicotine detoxication but also activates tobacco-specific procarcinogens to mutagenic products. We prepared a series of benzofuran and coumarin derivatives that have inhibitory effects on the activity of human CYP2A6. The reported compounds methoxalen and menthofuran had potent inhibitory effects on the activity of CYP2A6 with IC50 values of 0.47 µM and 1.27 µM, respectively. Synthetic benzofuran (4-methoxybenzofuran: IC₅₀=2.20 µM) and coumarin (5-methoxycoumarin: IC₅₀=0.13 µM and 6-methoxycoumarin: IC₅₀=0.64 µM) derivatives, which have more selective effects than those of methoxalen and menthofuran, exhibited comparable activities against CYP2A6. These compounds can be used as a lead compounds in the design of CYP2A6 inhibitor drugs to reduce smoking and tobacco-related cancers.

Topics: Aryl Hydrocarbon Hydroxylases; Benzofurans; Coumarins; Cytochrome P-450 CYP2A6; Enzyme Inhibitors; Humans; Models, Chemical; Monoterpenes; Protein Binding

A novel coumarin (1, mucodianin A), three new 2-arylbenzofurans (2-4, mucodianins B-D) along with four known ones were isolated from the vine stems of Mucuna birdwoodiana. Their structures were elucidated on basis of spectral analysis. This is the first report of 7-quinonylcoumarin (1) as stable form in natural products.

Topics: Benzofurans; Coumarins; Molecular Structure; Mucuna; Plant Stems

In a three-step sequence, an array of angularly fused polycyclic heterocycles with coumarin, benzofuran and pyridine rings were synthesized from 4-bromomethylcoumarins and salicylonitrile. All the final compounds were fully characterized and screened for anti-microbial, anti-inflammatory and analgesic activities. Several compounds exhibited promising inflammation inhibiting and anti-microbial properties.

Topics: Analgesics; Animals; Anti-Bacterial Agents; Anti-Inflammatory Agents; Benzofurans; Colony Count, Microbial; Coumarins; Heterocyclic Compounds, 4 or More Rings; Pain Measurement; Pyridines; Structure-Activity Relationship

Topics: Antihypertensive Agents; Benzofurans; Chemistry, Pharmaceutical; Coumarins; Furans; Mice; Pharmacology; Research