Cycloaddition of steroidal cyclic nitrones to C=N dipolarophiles: Stereoselective synthesis and antiproliferative effects of oxadiazolidinones in the estrone series

E. Mernyák, Judit Huber, Johanna Szabó, G. Schneider, A. Hetényi, L. Márk, Gábor Maász, Ágnes Berényi, Ida Kovács, Renáta Minorics, I. Zupkó, J. Wölfling

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Cyclic nitrones of estrone 3-methyl or 3-benzyl ether were reacted with phenyl isocyanate or nonsubstituted phenyl isocyanates as reactive C=N dipolarophiles, yielding condensed homosteroidal oxadiazolidinones. These dipolar cycloadditions were carried out under conventional heating or microwave irradiation. The chemo- and stereoselectivities of the reactions and the effects of the aromatic substituents on the reaction rates and yields were investigated and compared. The structures of the new products were determined by NMR (one- and two-dimensional) and MALDI-MS techniques, with C70 fullerenes as matrix in the latter case. The antiproliferative properties of the synthetized compounds were determined on a panel of human adherent cell lines (HeLa, MCF7, A2780 and A431) by means of MTT assays. Some of them exhibited activities comparable to that of the reference agent cisplatin. Flow cytometry indicated that one of the most potent agents (11a) resulted in a cell cycle blockade.

Original languageEnglish
Pages (from-to)1021-1028
Number of pages8
JournalSteroids
Volume78
Issue number10
DOIs
Publication statusPublished - 2013

Fingerprint

Cycloaddition
Estrone
Cycloaddition Reaction
Cells
Stereoselectivity
Microwave irradiation
Flow cytometry
Matrix-Assisted Laser Desorption-Ionization Mass Spectrometry
Microwaves
Ether
Heating
Cisplatin
Reaction rates
Assays
Cell Cycle
Flow Cytometry
Nuclear magnetic resonance
Cell Line
phenyl isocyanate
nitrones

Keywords

  • Antiproliferative effect
  • Dipolar cycloaddition
  • Estrone
  • Microwave irradiation
  • Oxadiazolidinone
  • Steroid MALDI-TOF

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Endocrinology
  • Molecular Biology
  • Organic Chemistry
  • Pharmacology

Cite this

Cycloaddition of steroidal cyclic nitrones to C=N dipolarophiles : Stereoselective synthesis and antiproliferative effects of oxadiazolidinones in the estrone series. / Mernyák, E.; Huber, Judit; Szabó, Johanna; Schneider, G.; Hetényi, A.; Márk, L.; Maász, Gábor; Berényi, Ágnes; Kovács, Ida; Minorics, Renáta; Zupkó, I.; Wölfling, J.

In: Steroids, Vol. 78, No. 10, 2013, p. 1021-1028.

Research output: Contribution to journalArticle

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