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O-Benzoyl-naltrexone.

Rui Yang¹, Guo-Hai Wang, Xia-Li Liu

¹Department of Pharmacology, Technical Center, Jiangsu Nhwa Pharma Corporation, Zhongshan Road No. 289, Xuzhou 221009, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|September 19, 2013

Summary

This study details the crystal structure of a naltrexone benzoate ester, revealing a specific dihedral angle between phenyl rings. Molecular interactions form chains in the crystal lattice, confirming known configurations.

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Area of Science:

Medicinal Chemistry
Crystallography
Pharmacology

Background:

Naltrexone is a key opioid receptor antagonist used in addiction treatment.
Understanding the molecular structure of naltrexone derivatives is crucial for drug design.
Opioid receptor antagonists play a vital role in managing opioid use disorder.

Purpose of the Study:

To elucidate the crystal structure and molecular conformation of the benzoate ester of naltrexone.
To investigate intermolecular interactions within the crystal lattice.
To confirm the absolute configuration of the synthesized compound.

Main Methods:

Single-crystal X-ray diffraction analysis was performed on the title compound.
The crystal structure was solved and refined to determine atomic coordinates and bond parameters.
Intermolecular interactions, such as hydrogen bonding, were analyzed.

Main Results:

The dihedral angle between the two phenyl rings in the molecule was determined to be 77.1(1)°.
A weak aromatic C-H⋯Ocarbox-yl hydrogen bond was identified, leading to chain formation along the a-axis.
The known absolute configuration of naltrexone was successfully inferred for the derivative.

Conclusions:

The crystal structure provides detailed insights into the spatial arrangement of the naltrexone benzoate ester.
Intermolecular hydrogen bonding plays a role in the solid-state packing of the compound.
This structural information can aid in the development of novel opioid receptor antagonists.