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Clostebol acetate.

Elisabetta Maccaroni¹, Andrea Mele, Renato Del Rosso

¹Department of Chemistry, Materials and Chemical Engineering "G. Natta", Politecnico di Milano, Via Mancinelli 7, I-20131 Milano, Italy.

Acta Crystallographica. Section E, Structure Reports Online

|November 18, 2011

Summary

This summary is machine-generated.

This study details the structure of a 4-chloro testosterone derivative, a compound with anabolic and topical therapeutic applications. Its specific stereochemistry and crystal interactions were precisely determined.

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Area of Science:

Medicinal Chemistry
Organic Chemistry
Crystallography

Background:

The title compound is a 4-chloro derivative of testosterone.
It functions as an anabolic androgenic agent and has topical applications in ophthalmology and dermatology.

Purpose of the Study:

To elucidate the absolute configurations and crystal structure of the 4-chloro testosterone derivative.
To understand the molecular conformation and intermolecular interactions in the crystalline state.

Main Methods:

X-ray crystallography was employed to determine the molecular structure.
Refinement of the Flack parameter was used to establish absolute configurations.
Analysis of bond lengths, angles, and intermolecular interactions was performed.

Main Results:

The absolute configurations at stereocenters 8, 9, 10, 13, 14, and 17 were determined as R, S, R, S, S, and S, respectively.
Steroid rings adopt specific conformations: chair for B and C, half-chair for A, and C(13) envelope for D.
Trans fusion was observed between rings B/C and C/D.
A weak C-H⋯O interaction was identified as the primary intermolecular force in the crystal.

Conclusions:

The study provides a detailed structural characterization of a significant testosterone derivative.
Understanding the structure-activity relationship can inform the development of new therapeutic agents.
The identified crystal packing interactions offer insights into solid-state properties.