Abstract
Intermolecular Cu(I)-catalyzed azide-alkyne cycloadditions of 15β-azido-17β-hydroxy-5α-androstan-3β-yl acetate with different terminal alkynes under optimized reaction conditions were carried out to furnish 15β-triazolyl derivatives in good yields. Subsequent oxidation of the 'click' products with the Jones reagent afforded the corresponding 17-ketones. All the synthetized compounds were tested on three malignant human cell lines (HeLa, MCF7 and A431) in order to investigate their antiproliferative activities in vitro. Evidence of cell cycle blockade and apoptosis induction was obtained for the most effective five selected compounds by means of flow cytometry and microscopic techniques. The 15β-triazolyl-5α-androstane framework may be considered an appropriate base for the design of steroidal antiproliferative agents.
| Original language | English |
|---|---|
| Pages (from-to) | 1396-1402 |
| Number of pages | 7 |
| Journal | Bioorganic and Medicinal Chemistry |
| Volume | 20 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - Feb 15 2012 |
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Keywords
- 1,3-Dipolar cycloaddition
- Antiproliferative activity
- Cu(I) catalysis
- Steroidal azides
- Triazoles
ASJC Scopus subject areas
- Pharmaceutical Science
- Drug Discovery
- Organic Chemistry
- Molecular Medicine
- Molecular Biology
- Clinical Biochemistry
- Biochemistry
Cite this
A facile 'click' approach to novel 15β-triazolyl-5α-androstane derivatives, and an evaluation of their antiproliferative activities in vitro. / Kádár, Zalán; Molnár, Judit; Schneider, G.; Zupkó, I.; Frank, E.
In: Bioorganic and Medicinal Chemistry, Vol. 20, No. 4, 15.02.2012, p. 1396-1402.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - A facile 'click' approach to novel 15β-triazolyl-5α-androstane derivatives, and an evaluation of their antiproliferative activities in vitro
AU - Kádár, Zalán
AU - Molnár, Judit
AU - Schneider, G.
AU - Zupkó, I.
AU - Frank, E.
PY - 2012/2/15
Y1 - 2012/2/15
N2 - Intermolecular Cu(I)-catalyzed azide-alkyne cycloadditions of 15β-azido-17β-hydroxy-5α-androstan-3β-yl acetate with different terminal alkynes under optimized reaction conditions were carried out to furnish 15β-triazolyl derivatives in good yields. Subsequent oxidation of the 'click' products with the Jones reagent afforded the corresponding 17-ketones. All the synthetized compounds were tested on three malignant human cell lines (HeLa, MCF7 and A431) in order to investigate their antiproliferative activities in vitro. Evidence of cell cycle blockade and apoptosis induction was obtained for the most effective five selected compounds by means of flow cytometry and microscopic techniques. The 15β-triazolyl-5α-androstane framework may be considered an appropriate base for the design of steroidal antiproliferative agents.
AB - Intermolecular Cu(I)-catalyzed azide-alkyne cycloadditions of 15β-azido-17β-hydroxy-5α-androstan-3β-yl acetate with different terminal alkynes under optimized reaction conditions were carried out to furnish 15β-triazolyl derivatives in good yields. Subsequent oxidation of the 'click' products with the Jones reagent afforded the corresponding 17-ketones. All the synthetized compounds were tested on three malignant human cell lines (HeLa, MCF7 and A431) in order to investigate their antiproliferative activities in vitro. Evidence of cell cycle blockade and apoptosis induction was obtained for the most effective five selected compounds by means of flow cytometry and microscopic techniques. The 15β-triazolyl-5α-androstane framework may be considered an appropriate base for the design of steroidal antiproliferative agents.
KW - 1,3-Dipolar cycloaddition
KW - Antiproliferative activity
KW - Cu(I) catalysis
KW - Steroidal azides
KW - Triazoles
UR - http://www.scopus.com/inward/record.url?scp=84857031226&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84857031226&partnerID=8YFLogxK
U2 - 10.1016/j.bmc.2012.01.008
DO - 10.1016/j.bmc.2012.01.008
M3 - Article
C2 - 22277592
AN - SCOPUS:84857031226
VL - 20
SP - 1396
EP - 1402
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
SN - 0968-0896
IS - 4
ER -