Microwave-assisted one-pot synthesis of steroid-quinoline hybrids and an evaluation of their antiproliferative activities on gynecological cancer cell lines

Ádám Baji, András Gyovai, J. Wölfling, Renáta Minorics, I. Ocsovszki, I. Zupkó, E. Frank

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8 Citations (Scopus)

Abstract

Novel D- and A-ring-fused quinolines in the estrone and 5α-androstane series were efficiently synthesized from the corresponding β-chlorovinyl aldehydes with different arylamines in DMF under microwave irradiation. The rates of the one-pot catalyst-free syntheses and the yields of the desired products were found to be affected significantly by the electronic and steric character of the substituents on the anilines and the different reactivities of rings D and A of the sterane skeleton. All the synthesized compounds were tested in vitro on human cervical (C33A, HeLa and SiHa) and breast (MCF-7, MDA-MB-231, MDA-MB-361 and T47D) cancer cell lines in order to investigate their antiproliferative activities in vitro. Evidence of cell cycle blockade and apoptosis induction was obtained for the most effective compound 14c by means of flow cytometry, caspase-3 activity determination and microscopic techniques.

Original languageEnglish
Pages (from-to)27501-27516
Number of pages16
JournalRSC Advances
Volume6
Issue number33
DOIs
Publication statusPublished - 2016

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Aniline Compounds
Steroids
Microwaves
Cells
Quinolines
Microwave irradiation
Flow cytometry
Estrone
Cell death
Aniline
Aldehydes
Caspase 3
Apoptosis
Catalysts
quinoline
androstane

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)

Cite this

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abstract = "Novel D- and A-ring-fused quinolines in the estrone and 5α-androstane series were efficiently synthesized from the corresponding β-chlorovinyl aldehydes with different arylamines in DMF under microwave irradiation. The rates of the one-pot catalyst-free syntheses and the yields of the desired products were found to be affected significantly by the electronic and steric character of the substituents on the anilines and the different reactivities of rings D and A of the sterane skeleton. All the synthesized compounds were tested in vitro on human cervical (C33A, HeLa and SiHa) and breast (MCF-7, MDA-MB-231, MDA-MB-361 and T47D) cancer cell lines in order to investigate their antiproliferative activities in vitro. Evidence of cell cycle blockade and apoptosis induction was obtained for the most effective compound 14c by means of flow cytometry, caspase-3 activity determination and microscopic techniques.",
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T1 - Microwave-assisted one-pot synthesis of steroid-quinoline hybrids and an evaluation of their antiproliferative activities on gynecological cancer cell lines

AU - Baji, Ádám

AU - Gyovai, András

AU - Wölfling, J.

AU - Minorics, Renáta

AU - Ocsovszki, I.

AU - Zupkó, I.

AU - Frank, E.

PY - 2016

Y1 - 2016

N2 - Novel D- and A-ring-fused quinolines in the estrone and 5α-androstane series were efficiently synthesized from the corresponding β-chlorovinyl aldehydes with different arylamines in DMF under microwave irradiation. The rates of the one-pot catalyst-free syntheses and the yields of the desired products were found to be affected significantly by the electronic and steric character of the substituents on the anilines and the different reactivities of rings D and A of the sterane skeleton. All the synthesized compounds were tested in vitro on human cervical (C33A, HeLa and SiHa) and breast (MCF-7, MDA-MB-231, MDA-MB-361 and T47D) cancer cell lines in order to investigate their antiproliferative activities in vitro. Evidence of cell cycle blockade and apoptosis induction was obtained for the most effective compound 14c by means of flow cytometry, caspase-3 activity determination and microscopic techniques.

AB - Novel D- and A-ring-fused quinolines in the estrone and 5α-androstane series were efficiently synthesized from the corresponding β-chlorovinyl aldehydes with different arylamines in DMF under microwave irradiation. The rates of the one-pot catalyst-free syntheses and the yields of the desired products were found to be affected significantly by the electronic and steric character of the substituents on the anilines and the different reactivities of rings D and A of the sterane skeleton. All the synthesized compounds were tested in vitro on human cervical (C33A, HeLa and SiHa) and breast (MCF-7, MDA-MB-231, MDA-MB-361 and T47D) cancer cell lines in order to investigate their antiproliferative activities in vitro. Evidence of cell cycle blockade and apoptosis induction was obtained for the most effective compound 14c by means of flow cytometry, caspase-3 activity determination and microscopic techniques.

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