Synthesis, structure, and in vitro antitumor activity of some glycoside derivatives of ferrocenyl-chalcones and ferrocenyl-pyrazolines

Virág Zsoldos-Mády, A. Csámpai, Rita Szabó, Erika Mészáros-Alapi, Judit Pásztor, F. Hudecz, P. Sohár

Research output: Contribution to journalArticle

71 Citations (Scopus)

Abstract

Some new glycosides of 3-ferrocenyl-1-(4′-hydroxyphenyl)-prop-2-en-1- one were prepared and transformed into the corresponding pyrazoline and pyrazole derivatives. Using methyl-hydrazine, formation of regioisomers was observed. DDQ was found to be a mild and efficient reagent for the pyrazoline-pyrazole dehydroaromatization process. The structure of the new compounds was proved by IR and NMR spectroscopy. The in vitro antitumor activity of the substances was investigated against human leukemia (HL-60) cells by the MTT method. Among these new compounds some chalcone derivatives (3 a, 36, 5a, and 5b) showed attractive in vitro antitumor effects on human leukemia cells. These molecules contained ferrocenyl moieties and a p-hydroxy-phenolic ring or a size-independent apolar substitution of that.

Original languageEnglish
Pages (from-to)1119-1125
Number of pages7
JournalChemMedChem
Volume1
Issue number10
DOIs
Publication statusPublished - Oct 2006

Fingerprint

Chalcones
Glycosides
Leukemia
Monomethylhydrazine
Derivatives
Chalcone
HL-60 Cells
Nuclear magnetic resonance spectroscopy
Infrared spectroscopy
Substitution reactions
Magnetic Resonance Spectroscopy
Molecules
pyrazole
In Vitro Techniques

Keywords

  • Anticancer agents
  • Ferrocenes
  • Glycosides
  • IR spectroscopy
  • Nitrogen heterocycles
  • NMR spectroscopy

ASJC Scopus subject areas

  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry
  • Molecular Medicine

Cite this

Synthesis, structure, and in vitro antitumor activity of some glycoside derivatives of ferrocenyl-chalcones and ferrocenyl-pyrazolines. / Zsoldos-Mády, Virág; Csámpai, A.; Szabó, Rita; Mészáros-Alapi, Erika; Pásztor, Judit; Hudecz, F.; Sohár, P.

In: ChemMedChem, Vol. 1, No. 10, 10.2006, p. 1119-1125.

Research output: Contribution to journalArticle

Zsoldos-Mády, Virág ; Csámpai, A. ; Szabó, Rita ; Mészáros-Alapi, Erika ; Pásztor, Judit ; Hudecz, F. ; Sohár, P. / Synthesis, structure, and in vitro antitumor activity of some glycoside derivatives of ferrocenyl-chalcones and ferrocenyl-pyrazolines. In: ChemMedChem. 2006 ; Vol. 1, No. 10. pp. 1119-1125.
@article{c90e59c2db9f4d81906164749dccbffc,
title = "Synthesis, structure, and in vitro antitumor activity of some glycoside derivatives of ferrocenyl-chalcones and ferrocenyl-pyrazolines",
abstract = "Some new glycosides of 3-ferrocenyl-1-(4′-hydroxyphenyl)-prop-2-en-1- one were prepared and transformed into the corresponding pyrazoline and pyrazole derivatives. Using methyl-hydrazine, formation of regioisomers was observed. DDQ was found to be a mild and efficient reagent for the pyrazoline-pyrazole dehydroaromatization process. The structure of the new compounds was proved by IR and NMR spectroscopy. The in vitro antitumor activity of the substances was investigated against human leukemia (HL-60) cells by the MTT method. Among these new compounds some chalcone derivatives (3 a, 36, 5a, and 5b) showed attractive in vitro antitumor effects on human leukemia cells. These molecules contained ferrocenyl moieties and a p-hydroxy-phenolic ring or a size-independent apolar substitution of that.",
keywords = "Anticancer agents, Ferrocenes, Glycosides, IR spectroscopy, Nitrogen heterocycles, NMR spectroscopy",
author = "Vir{\'a}g Zsoldos-M{\'a}dy and A. Cs{\'a}mpai and Rita Szab{\'o} and Erika M{\'e}sz{\'a}ros-Alapi and Judit P{\'a}sztor and F. Hudecz and P. Soh{\'a}r",
year = "2006",
month = "10",
doi = "10.1002/cmdc.200600052",
language = "English",
volume = "1",
pages = "1119--1125",
journal = "ChemMedChem",
issn = "1860-7179",
publisher = "John Wiley and Sons Ltd",
number = "10",

}

TY - JOUR

T1 - Synthesis, structure, and in vitro antitumor activity of some glycoside derivatives of ferrocenyl-chalcones and ferrocenyl-pyrazolines

AU - Zsoldos-Mády, Virág

AU - Csámpai, A.

AU - Szabó, Rita

AU - Mészáros-Alapi, Erika

AU - Pásztor, Judit

AU - Hudecz, F.

AU - Sohár, P.

PY - 2006/10

Y1 - 2006/10

N2 - Some new glycosides of 3-ferrocenyl-1-(4′-hydroxyphenyl)-prop-2-en-1- one were prepared and transformed into the corresponding pyrazoline and pyrazole derivatives. Using methyl-hydrazine, formation of regioisomers was observed. DDQ was found to be a mild and efficient reagent for the pyrazoline-pyrazole dehydroaromatization process. The structure of the new compounds was proved by IR and NMR spectroscopy. The in vitro antitumor activity of the substances was investigated against human leukemia (HL-60) cells by the MTT method. Among these new compounds some chalcone derivatives (3 a, 36, 5a, and 5b) showed attractive in vitro antitumor effects on human leukemia cells. These molecules contained ferrocenyl moieties and a p-hydroxy-phenolic ring or a size-independent apolar substitution of that.

AB - Some new glycosides of 3-ferrocenyl-1-(4′-hydroxyphenyl)-prop-2-en-1- one were prepared and transformed into the corresponding pyrazoline and pyrazole derivatives. Using methyl-hydrazine, formation of regioisomers was observed. DDQ was found to be a mild and efficient reagent for the pyrazoline-pyrazole dehydroaromatization process. The structure of the new compounds was proved by IR and NMR spectroscopy. The in vitro antitumor activity of the substances was investigated against human leukemia (HL-60) cells by the MTT method. Among these new compounds some chalcone derivatives (3 a, 36, 5a, and 5b) showed attractive in vitro antitumor effects on human leukemia cells. These molecules contained ferrocenyl moieties and a p-hydroxy-phenolic ring or a size-independent apolar substitution of that.

KW - Anticancer agents

KW - Ferrocenes

KW - Glycosides

KW - IR spectroscopy

KW - Nitrogen heterocycles

KW - NMR spectroscopy

UR - http://www.scopus.com/inward/record.url?scp=33750397051&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33750397051&partnerID=8YFLogxK

U2 - 10.1002/cmdc.200600052

DO - 10.1002/cmdc.200600052

M3 - Article

C2 - 16944543

AN - SCOPUS:33750397051

VL - 1

SP - 1119

EP - 1125

JO - ChemMedChem

JF - ChemMedChem

SN - 1860-7179

IS - 10

ER -