Novel naphtho[2,3-b]furan-2,4,9(3H)-trione derivatives as potent ERα inhibitors: design, regioselective synthesis, HMBC-NMR characterization, in silico molecular Docking and ADME studies.

Authors

Seyede Bita Sajjadi, Abolfazl Olyaei, Monir Shalbafan

Published in

BMC chemistry. Volume 19. Issue 1. Pages 253. Aug 31, 2025. Epub Aug 31, 2025.

Abstract

In this study, novel linear 3-(arylamino)naphtho[2,3-b]furan-2,4,9(3H)-trione derivatives has been synthesized via annulation reaction of 2-hydroxy-1,4-naphthoquinone with aromatic amines and glyoxylic acid monohydrate using p-TSOH as catalyst at ambient temperature for the first time. The mechanism proceeds via an initial intermolecular aldol condensation, subsequent Michael addition, and final intramolecular nucleophilic annulation. The linear or angular configurations of the products was confirmed through ¹-¹³ C heteronuclear multiple-bond correlation (HMBC) analysis. To evaluate the inhibitory activity of the synthesized compounds, computational methods such as molecular docking and ADME analysis were employed. Compounds 4h and 4i displayed potent activity against tested estrogen receptor alpha (ERα) as compared to Doxorubicin.

PMID:
40887587
Bibliographic data and abstract were imported from PubMed on 01 Sep 2025.

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