The X-ray Investigation of 16α,17α-Thiazolidine Derivatives of Δ4- and Δ5-Pregnanes and Conformational Analysis of their Oxathiolane Analog

Authors

Sergey Lindeman, Marquette UniversityFollow
T. V. Timofeeva, Academy of Sciences of the USSRFollow
V. E. Shklover, Academy of Sciences of the USSRFollow
Yu T. Struchkov, Academy of Sciences of the USSRFollow
A. M. Turuta, Academy of Sciences of the USSRFollow
Alexey V. Kamernitzky, Academy of Sciences of the USSRFollow

Document Type

Article

Language

eng

Publication Date

2-1984

Publisher

Elsevier

Source Publication

Steroids

Source ISSN

0039-128X

Abstract

An X-ray study of 3,20-dioxo-4-pregnene-[16α, 17α−d]- -2',2'-dimethylthiazolidine (I) and 3β-hydroxy-20-oxo-5- -pregnene-[16α,17α−d]-2',2'-dimethylthiazolidine (II) has been carried out.

Two independent molecules in crystal II have significantly different conformations of the D and E rings, although according to the atom-atom potential calculations the energy of interaction of these molecules with their neighbors in crystal is the same. The calculation of conformational energy of 3,20-dioxo-4-pregnene-[17α, 16α−d]-2',2'- -dimethyloxathiolane (III) by the molecular mechanics method (MMM) indicates a possibility of existence of two similar conformers also for this molecule. The MMM calculation shows also that the conformation of molecule III (as well as progesterone) with the 17β-acetyl group torsion angle C(16)C(17)C(20)O(20) close to -120° is possible.

Comments

Steroids, Vol. 43, No. 2 (February 1084): 125-145. DOI.

Sergey Lindeman was affiliated with Academy of Sciences of the USSR at the time of publication.

Recommended Citation

Lindeman, Sergey; Timofeeva, T. V.; Shklover, V. E.; Struchkov, Yu T.; Turuta, A. M.; and Kamernitzky, Alexey V., "The X-ray Investigation of 16α,17α-Thiazolidine Derivatives of Δ4- and Δ5-Pregnanes and Conformational Analysis of their Oxathiolane Analog" (1984). Chemistry Faculty Research and Publications. 741.
https://epublications.marquette.edu/chem_fac/741