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Synthesis and Cytotoxicity Evaluation of Dehydroepiandrosterone Derivatives by Iron-Catalyzed Stereoselective Hydroamination.
- Source :
-
Chemical & pharmaceutical bulletin [Chem Pharm Bull (Tokyo)] 2023 May 01; Vol. 71 (5), pp. 349-353. Date of Electronic Publication: 2023 Mar 02. - Publication Year :
- 2023
-
Abstract
- The direct modification of structurally complex natural product dehydroepiandrosterone (DHEA) through iron-catalyzed direct hydroamination of DHEA with various nitro(hetero)arenes was carried out to afford 5α-arylamino-DHEAs (1-25) in good yields (53-72%). Though as a radical reaction, it features high stereoselectivity, and only the 5α-substituted derivatives were produced. The in vitro antiproliferative activity of these synthesized compounds against the human breast cancer MCF-7 cell was evaluated, showing that most of DHEA analogues possessed the moderate cytotoxic activity. The preliminary structure-activity relationship analysis revealed that the electron-withdrawing groups installed at the para-position of arylamine ring had a great contribution to the improvement of the DHEA's cytotoxic potency. Among them, (4-trifluoromethylaniline)-DHEA (4) displayed the most potent cytotoxicity, with an IC <subscript>50</subscript> value of 19.3 µM, which was 2.3-fold more active than DHEA.
Details
- Language :
- English
- ISSN :
- 1347-5223
- Volume :
- 71
- Issue :
- 5
- Database :
- MEDLINE
- Journal :
- Chemical & pharmaceutical bulletin
- Publication Type :
- Academic Journal
- Accession number :
- 36858603
- Full Text :
- https://doi.org/10.1248/cpb.c22-00857