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001-es BibID:BIBFORM090960
035-os BibID:(WOS)000595546200005 (Scopus)85096236870
Első szerző:Bús Csaba
Cím:Oxidized Juncuenin B Analogues with Increased Antiproliferative Activity on Human Adherent Cell Lines: Semisynthesis and Biological Evaluation / Csaba Bús, Ágnes Kulmány, Norbert Kúsz, Tímea Gonda, István Zupkó, Attila Mándi, Tibor Kurtán, Barbara Tóth, Judit Hohmann, Attila Hunyadi, Andrea Vasas
Dátum:2020
ISSN:0163-3864 1520-6025
Megjegyzések:Phenanthrenes have become the subject of intensive research during the past decades because of their structural diversity and wide range of pharmacological activities. Earlier studies demonstrated that semisynthetic derivatization of these natural compounds could result in more active agents, and oxidative transformations are particularly promising in this regard. In our work, a natural phenanthrene, juncuenin B, was transformed by hypervalent iodine(III) reagents using a diversity-oriented approach. Eleven racemic semisynthetic compounds were produced, the majority containing an alkyl substituted p-quinol ring. Purification of the compounds was carried out by chromatographic techniques, and their structures were elucidated by 1D and 2D NMR spectroscopic methods. Stereoisomers of the bioactive derivatives were separated by chiral-phase HPLC and the absolute configurations of the active compounds, 2,6-dioxo-1,8a-dimethoxy-1,7-dimethyl-8-vinyl-9,10-dihydrophenanthrenes (1a-d), and 8a-ethoxy-1,7-dimethyl-6-oxo-8-vinyl-9,10-dihydrophenanthrene-2-ols (7a,b) were determined by ECD measurements and TDDFT-ECD calculations. The antiproliferative activities of the compounds were tested on different (MCF-7, T47D, HeLa, SiHa, C33A, A2780) human gynecological cancer cell lines. Compounds 1a-d, 4a, 6a, and 7a possessed higher activity than juncuenin B on several tumor cell lines. The structure-activity relationship studies suggested that the p-quinol (2,5-cyclohexadien-4-hydroxy-1-one) moiety has a considerable effect on the antiproliferative properties, and substantial differences could be identified in the activities of the stereoisomers.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
folyóiratcikk
Megjelenés:Journal of Natural Products. - 83 : 11 (2020), p. 3250-3261. -
További szerzők:Kulmány Ágnes Kúsz Norbert Gonda Tímea Zupkó István Mándi Attila (1981-) (vegyész, német szakfordító) Kurtán Tibor (1973-) (vegyész, angol szakfordító) Tóth Barbara Hohmann Judit Hunyadi Attila Vasas Andrea
Pályázati támogatás:UNKP-18-3-SZTE-169
Egyéb
UNKP-19-3-SZTE-169
Egyéb
20391-3/2018/FEKUSTRAT
Egyéb
NKFIH K128963
Egyéb
NKFIH K119770
Egyéb
NKFIH K120181
Egyéb
GINOP-2.3.2-15-2016-00012
GINOP
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