Construction of benzofuranone library via a metal-free, one-pot intermolecular condensation, and their application as efficient estrogen receptor β modulators

Facile synthesis of benzofuranone was achieved through a metal-free, one-pot intermolecular condensation between α-hydroxy aryl ketones and resorcinol derivatives. A library of 20 compounds with moderate to good overall yields was prepared. These compounds showed strong binding toward estrogen recep...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019-12, Vol.55 (97), p.14570-14573
Main Authors: Peng, Xueke, Hu, Zhiye, Zhang, Jing, Ning, Wentao, Zhang, Silong, Dong, Chune, Shi, Xiaodong, Zhou, Hai-Bing
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Aromatic compounds
Benzofurans - chemical synthesis
Benzofurans - chemistry
Benzofurans - pharmacology
Cell Line, Tumor
Cell Proliferation - drug effects
Crystallography
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Estrogen Receptor alpha - antagonists & inhibitors
Estrogen Receptor alpha - metabolism
Estrogen Receptor beta - agonists
Estrogen Receptor beta - metabolism
Estrogen Receptor Modulators - chemical synthesis
Estrogen Receptor Modulators - chemistry
Estrogen Receptor Modulators - pharmacology
Estrogens
Humans
Ketones
Models, Molecular
Modulators
Molecular Structure
Receptors
Selectivity
Structure-Activity Relationship
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Summary:Facile synthesis of benzofuranone was achieved through a metal-free, one-pot intermolecular condensation between α-hydroxy aryl ketones and resorcinol derivatives. A library of 20 compounds with moderate to good overall yields was prepared. These compounds showed strong binding toward estrogen receptors along with good selectivity for ERβ (>190-fold over ERα). Anti-proliferative activity on DU-145, U-87, and MCF-7 cells gave inhibition IC values in the low μM range, which suggested the promising potential therapeutic applications of these new classes of benzofuranones.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc05756k