Synthesis, stereochemistry and cytotoxic activity of novel steroidal 16-spiro-1,3,2-dioxaphosphorinanes

J. Wölfling, Piroska Kovács-Pénzes, I. Zupkó, G. Schneider, E. Frank

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The epimeric pairs a and b of novel steroidal 16-spiro-dioxaphosphorinanes 4-8 were synthetized via the phosphorylation of 16,16-bis(hydroxymethyl)androst- 4-ene-3,17-dione (2) and their stereostructures were investigated by NMR methods. The dioxaphosphorinane moiety exists mainly as one of the possible chair conformers or as a chair-twist equilibrium in solution as a consequence of the rigidity of the sterane framework. The contributions of the conformers depend strongly on the configuration of the P atom and the stereoelectronic properties of the substituents on it. The antiproliferative activities of the structurally related products were determined in vitro with the MTT assay on three malignant human cell lines (HeLa, MCF7 and A431).

Original languageEnglish
Pages (from-to)39-44
Number of pages6
JournalJournal of Molecular Structure
Volume1013
DOIs
Publication statusPublished - Apr 11 2012

Fingerprint

Stereochemistry
Phosphorylation
Androstenedione
Rigidity
Assays
Cells
Nuclear magnetic resonance
Atoms

Keywords

  • Antiproliferative effect
  • Dioxaphosphorinanes
  • Phosphorylations
  • Spiro compounds
  • Stereostructure
  • Steroids

ASJC Scopus subject areas

  • Spectroscopy
  • Analytical Chemistry
  • Inorganic Chemistry
  • Organic Chemistry

Cite this

@article{963719c024e44a3988eaa910cfc7a953,
title = "Synthesis, stereochemistry and cytotoxic activity of novel steroidal 16-spiro-1,3,2-dioxaphosphorinanes",
abstract = "The epimeric pairs a and b of novel steroidal 16-spiro-dioxaphosphorinanes 4-8 were synthetized via the phosphorylation of 16,16-bis(hydroxymethyl)androst- 4-ene-3,17-dione (2) and their stereostructures were investigated by NMR methods. The dioxaphosphorinane moiety exists mainly as one of the possible chair conformers or as a chair-twist equilibrium in solution as a consequence of the rigidity of the sterane framework. The contributions of the conformers depend strongly on the configuration of the P atom and the stereoelectronic properties of the substituents on it. The antiproliferative activities of the structurally related products were determined in vitro with the MTT assay on three malignant human cell lines (HeLa, MCF7 and A431).",
keywords = "Antiproliferative effect, Dioxaphosphorinanes, Phosphorylations, Spiro compounds, Stereostructure, Steroids",
author = "J. W{\"o}lfling and Piroska Kov{\'a}cs-P{\'e}nzes and I. Zupk{\'o} and G. Schneider and E. Frank",
year = "2012",
month = "4",
day = "11",
doi = "10.1016/j.molstruc.2012.01.013",
language = "English",
volume = "1013",
pages = "39--44",
journal = "Journal of Molecular Structure",
issn = "0022-2860",
publisher = "Elsevier",

}

TY - JOUR

T1 - Synthesis, stereochemistry and cytotoxic activity of novel steroidal 16-spiro-1,3,2-dioxaphosphorinanes

AU - Wölfling, J.

AU - Kovács-Pénzes, Piroska

AU - Zupkó, I.

AU - Schneider, G.

AU - Frank, E.

PY - 2012/4/11

Y1 - 2012/4/11

N2 - The epimeric pairs a and b of novel steroidal 16-spiro-dioxaphosphorinanes 4-8 were synthetized via the phosphorylation of 16,16-bis(hydroxymethyl)androst- 4-ene-3,17-dione (2) and their stereostructures were investigated by NMR methods. The dioxaphosphorinane moiety exists mainly as one of the possible chair conformers or as a chair-twist equilibrium in solution as a consequence of the rigidity of the sterane framework. The contributions of the conformers depend strongly on the configuration of the P atom and the stereoelectronic properties of the substituents on it. The antiproliferative activities of the structurally related products were determined in vitro with the MTT assay on three malignant human cell lines (HeLa, MCF7 and A431).

AB - The epimeric pairs a and b of novel steroidal 16-spiro-dioxaphosphorinanes 4-8 were synthetized via the phosphorylation of 16,16-bis(hydroxymethyl)androst- 4-ene-3,17-dione (2) and their stereostructures were investigated by NMR methods. The dioxaphosphorinane moiety exists mainly as one of the possible chair conformers or as a chair-twist equilibrium in solution as a consequence of the rigidity of the sterane framework. The contributions of the conformers depend strongly on the configuration of the P atom and the stereoelectronic properties of the substituents on it. The antiproliferative activities of the structurally related products were determined in vitro with the MTT assay on three malignant human cell lines (HeLa, MCF7 and A431).

KW - Antiproliferative effect

KW - Dioxaphosphorinanes

KW - Phosphorylations

KW - Spiro compounds

KW - Stereostructure

KW - Steroids

UR - http://www.scopus.com/inward/record.url?scp=84858328108&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84858328108&partnerID=8YFLogxK

U2 - 10.1016/j.molstruc.2012.01.013

DO - 10.1016/j.molstruc.2012.01.013

M3 - Article

AN - SCOPUS:84858328108

VL - 1013

SP - 39

EP - 44

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

SN - 0022-2860

ER -