Synthesis of novel 17-(5′-iodo)triazolyl-3-methoxyestrane epimers via Cu(I)-catalyzed azide-alkyne cycloadditon, and an evaluation of their cytotoxic activity in vitro Dedicated to Professor Irén Vincze on the occasion of her 85th birthday

G. Schneider, Tamás Görbe, E. Mernyák, J. Wölfling, Tamás Holczbauer, M. Czugler, P. Sohár, Renáta Minorics, I. Zupkó

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6 Citations (Scopus)

Abstract

The regioselective Cu(I)-catalyzed 1,3-dipolar cycloaddition of 3-methoxyestrane 17α- and 17β-azide epimers (3 and 5) with different terminal alkynes afforded novel 1,4-substituted triazolyl derivatives (8a-f and 11a-f). If the Ph3P in the classical CuAAC process was replaced by Et3N, the formation of small quantities of 5-iodotriazoles (9a-f and 11a-f) was observed. For the preparation of 5-iodo-1,2,3-triazoles (9a-f and 11a-f), an improved method was developed, directly from steroidal azides and terminal alkynes, in reactions mediated by CuI and ICl as iodinating agents. The antiproliferative activities of the structurally related triazoles were determined in vitro with the microculture tetrazolium assay on six malignant human cell lines of gynecological origin (HeLa, A2780, MCF7, MDA-MB-231, MDA-MB-361 and T47D). X-ray analysis revealed the presence of the iodo substituent on the 1,2,3-triazole ring.

Original languageEnglish
Pages (from-to)153-165
Number of pages13
JournalSteroids
Volume98
DOIs
Publication statusPublished - Jun 17 2015

Fingerprint

Triazoles
Alkynes
Azides
Cycloaddition
X ray analysis
Cycloaddition Reaction
Assays
Cells
X-Rays
Derivatives
Cell Line
In Vitro Techniques
5-iodo-1,2,3-triazole

Keywords

  • 1,3-Dipolar cycloaddition
  • Cytotoxic activity
  • Iodotriazoles
  • X-ray analysis

ASJC Scopus subject areas

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

Cite this

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title = "Synthesis of novel 17-(5′-iodo)triazolyl-3-methoxyestrane epimers via Cu(I)-catalyzed azide-alkyne cycloadditon, and an evaluation of their cytotoxic activity in vitro Dedicated to Professor Ir{\'e}n Vincze on the occasion of her 85th birthday",
abstract = "The regioselective Cu(I)-catalyzed 1,3-dipolar cycloaddition of 3-methoxyestrane 17α- and 17β-azide epimers (3 and 5) with different terminal alkynes afforded novel 1,4-substituted triazolyl derivatives (8a-f and 11a-f). If the Ph3P in the classical CuAAC process was replaced by Et3N, the formation of small quantities of 5-iodotriazoles (9a-f and 11a-f) was observed. For the preparation of 5-iodo-1,2,3-triazoles (9a-f and 11a-f), an improved method was developed, directly from steroidal azides and terminal alkynes, in reactions mediated by CuI and ICl as iodinating agents. The antiproliferative activities of the structurally related triazoles were determined in vitro with the microculture tetrazolium assay on six malignant human cell lines of gynecological origin (HeLa, A2780, MCF7, MDA-MB-231, MDA-MB-361 and T47D). X-ray analysis revealed the presence of the iodo substituent on the 1,2,3-triazole ring.",
keywords = "1,3-Dipolar cycloaddition, Cytotoxic activity, Iodotriazoles, X-ray analysis",
author = "G. Schneider and Tam{\'a}s G{\"o}rbe and E. Merny{\'a}k and J. W{\"o}lfling and Tam{\'a}s Holczbauer and M. Czugler and P. Soh{\'a}r and Ren{\'a}ta Minorics and I. Zupk{\'o}",
year = "2015",
month = "6",
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doi = "10.1016/j.steroids.2015.02.018",
language = "English",
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T1 - Synthesis of novel 17-(5′-iodo)triazolyl-3-methoxyestrane epimers via Cu(I)-catalyzed azide-alkyne cycloadditon, and an evaluation of their cytotoxic activity in vitro Dedicated to Professor Irén Vincze on the occasion of her 85th birthday

AU - Schneider, G.

AU - Görbe, Tamás

AU - Mernyák, E.

AU - Wölfling, J.

AU - Holczbauer, Tamás

AU - Czugler, M.

AU - Sohár, P.

AU - Minorics, Renáta

AU - Zupkó, I.

PY - 2015/6/17

Y1 - 2015/6/17

N2 - The regioselective Cu(I)-catalyzed 1,3-dipolar cycloaddition of 3-methoxyestrane 17α- and 17β-azide epimers (3 and 5) with different terminal alkynes afforded novel 1,4-substituted triazolyl derivatives (8a-f and 11a-f). If the Ph3P in the classical CuAAC process was replaced by Et3N, the formation of small quantities of 5-iodotriazoles (9a-f and 11a-f) was observed. For the preparation of 5-iodo-1,2,3-triazoles (9a-f and 11a-f), an improved method was developed, directly from steroidal azides and terminal alkynes, in reactions mediated by CuI and ICl as iodinating agents. The antiproliferative activities of the structurally related triazoles were determined in vitro with the microculture tetrazolium assay on six malignant human cell lines of gynecological origin (HeLa, A2780, MCF7, MDA-MB-231, MDA-MB-361 and T47D). X-ray analysis revealed the presence of the iodo substituent on the 1,2,3-triazole ring.

AB - The regioselective Cu(I)-catalyzed 1,3-dipolar cycloaddition of 3-methoxyestrane 17α- and 17β-azide epimers (3 and 5) with different terminal alkynes afforded novel 1,4-substituted triazolyl derivatives (8a-f and 11a-f). If the Ph3P in the classical CuAAC process was replaced by Et3N, the formation of small quantities of 5-iodotriazoles (9a-f and 11a-f) was observed. For the preparation of 5-iodo-1,2,3-triazoles (9a-f and 11a-f), an improved method was developed, directly from steroidal azides and terminal alkynes, in reactions mediated by CuI and ICl as iodinating agents. The antiproliferative activities of the structurally related triazoles were determined in vitro with the microculture tetrazolium assay on six malignant human cell lines of gynecological origin (HeLa, A2780, MCF7, MDA-MB-231, MDA-MB-361 and T47D). X-ray analysis revealed the presence of the iodo substituent on the 1,2,3-triazole ring.

KW - 1,3-Dipolar cycloaddition

KW - Cytotoxic activity

KW - Iodotriazoles

KW - X-ray analysis

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