New steroid-fused P-heterocycles. Part II. Synthesis and conformational study of oxazaphosphorino[16,17-e]estrone derivatives

E. Frank, Brigitta Kazi, Zoltán Mucsi, K. Ludányi, G. Keglevich

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

16β-Aminomethyl-17β-hydroxyestrone 3-methyl ether 6 and its N-propyl (17), N-benzyl (18) and N-arylmethyl derivatives (19-22) were subjected to ring closure reactions with phenylphosphonic dichloride in order to synthetize P-epimeric oxazaphosphorinanes 23a, 24-29 in which the hetero ring is condensed to ring D of the sterane skeleton. The stereostructures of the products were evaluated by 1H, 13C and 31P NMR spectroscopy. The geometry was optimized by utilizing the B3LYP DFT method. The NMR spectral data and the results of the ab initio calculations demonstrated that the stereostructure of the hetero ring was strongly affected by the rigid sterane framework condensed to it, and the phosphoramidate ring proved to adopt predominantly a distorted-boat conformation, regardless of the P-configuration.

Original languageEnglish
Pages (from-to)446-458
Number of pages13
JournalSteroids
Volume72
Issue number5
DOIs
Publication statusPublished - May 2007

Fingerprint

Hydroxyestrones
Methyl Ethers
Ships
Estrone
Boats
Skeleton
Discrete Fourier transforms
Nuclear magnetic resonance spectroscopy
Conformations
Magnetic Resonance Spectroscopy
Steroids
Nuclear magnetic resonance
Derivatives
Geometry
phosphoramidic acid
Carbon-13 Magnetic Resonance Spectroscopy

Keywords

  • Conformational study
  • Epimers
  • Heteroestrone derivatives
  • Oxazaphosphorinanes

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology
  • Molecular Biology

Cite this

New steroid-fused P-heterocycles. Part II. Synthesis and conformational study of oxazaphosphorino[16,17-e]estrone derivatives. / Frank, E.; Kazi, Brigitta; Mucsi, Zoltán; Ludányi, K.; Keglevich, G.

In: Steroids, Vol. 72, No. 5, 05.2007, p. 446-458.

Research output: Contribution to journalArticle

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