6468-49-1

Usage

Uses

Used in Pharmaceutical Industry:
3-hydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one is used as a scaffold for the development of new drug molecules due to its unique structure and biological activities. Its anti-inflammatory and antioxidant properties make it a promising candidate for the treatment of various diseases and conditions.
Used in Natural Products:
3-hydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one is found in certain natural products, which may contribute to their therapeutic effects. Its presence in these products highlights the potential for further research and development of natural-based pharmaceuticals.

Upstream product

• 92549-46-7 1-(2,4-dihydroxy-phenyl)-2-(2-methoxy-phenyl)-ethanone 
• 63909-40-0 7-hydroxy-3-(2-methoxyphenyl)-4H-chromen-4-one 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 94303-12-5 ethyl 2-(2,4-dimethoxyphenyl)benzofuran-3-carboxylate 
• 108-95-2 phenol 
• 60946-77-2 ethyl 3-(3,5-dimethoxyphenyl)-3-oxopropanoate 
• 79762-15-5 6a,11a-dihydro-3-hydroxy-6H-benzofuro<3,2-c><1>benzopyran 

Relevant academic research and scientific papers

Copper-catalyzed intramolecular cross dehydrogenative coupling approach to coumestans from 2′-hydroxyl-3-arylcoumarins

A copper-catalyzed intramolecular cross dehydrogenative C-O coupling reaction of 2′-hydroxyl-3-arylcoumarins was developed. This protocol provided a facile and efficient strategy for the construction of natural coumestans and derivatives in moderate to high yields. This transformation exhibited good functional group compatibility and was amenable to substrates with free phenolic hydroxyl groups.

Copper-mediated synthesis of coumestans via C(sp2)-H functionalization: Protective group free route to coumestrol and 4′-O-methylcoumestrol

A simple and efficient two step synthesis of coumestans is described. The key reaction in the synthesis is the use of easily available Cu(OAc)2 for C[sbnd]H functionalization of 3-(2-hydroxyphenyl)coumarin to give coumestan ring system via formal oxidative cyclization. This approach provided a short protective group free route to naturally occurring coumestrol and 4′-O-methylcoumestrol.

COUMESTAN, COUMESTROL, COUMESTAN DERIVATIVES AND PROCESSES OF MAKING THE SAME AND USES OF SAME

The present invention provides new coumestans compounds and processes for the preparation of coumestans, pharmaceutical compositions having a coumestan as an active pharmaceutical ingredient, and methods of utilizing coumestans as selective estrogen receptor modulators (SERMs) for treating estrogen dependent diseases such as breast cancer.

Aerobic iron-based cross-dehydrogenative coupling enables efficient diversity-oriented synthesis of coumestrol-based selective estrogen receptor modulators

An iron-based cross-dehydrogenative coupling (CDC) approach was applied for the diversity-oriented synthesis of coumestrol-based selective estrogen receptor modulators (SERMs), representing the first application of CDC chemistry in natural product synthesis. The first stage of the two-step synthesis of coumestrol involved a modified aerobic oxidative cross-coupling between ethyl 2-(2,4-dimethoxybenzoyl)acetate and 3-methoxyphenol, with FeCl3 (10 mol %) as the catalyst. The benzofuran coupling product was then subjected to sequential deprotection and lactonization steps, affording the natural product in 59 % overall yield. Based on this new methodology other coumestrol analogues were prepared, and their effects on the proliferation of the estrogen receptor (ER)-dependent MCF-7 and of the ER-independent MDA-MB-231 breast cancer cells were tested. As a result, new types of estrogen receptor ligands having an acetamide group instead of the 9-hydroxyl group of coumestrol were discovered. Both 9-acetamido-coumestrol and 8-acetamidocoumestrol were found more active than the natural product against estrogen-dependent MCF-7 breast cancer cells, with IC50 values of 30 and 9 nM, respectively. Green medicinal chemistry: An iron-based cross-dehydrogenative coupling (CDC) approach was applied for the diversity-oriented synthesis of coumestrol-based selective estrogen receptor modulators (SERMs), representing the first application of CDC chemistry in natural product synthesis (see scheme; DCE=dichloroethane). Copyright

SUBSTITUTED BENZFUROCHROMENES AND RELATED COMPOUNDS FOR THE PREVENTION AND TREATMENT OF BONE RELATED DISORDERS

The present invention relates to novel substituted benzfurochromenes and related compounds having the general formula (I), salts and chiral, achiral derivatives thereof; wherein R1, R2, R3, R4, R5, R