Collect. Czech. Chem. Commun. 2005, 70, 237-246

Synthesis and Crystal Structure of 17-Allyl-4,5-anhydro-7α-[(R)-1-hydroxy-1-methyl-3-(2-thienyl)propyl]-6-methoxy-6,14-ethanomorphinan-3,4,5-triol

He Liu*, Jingyan Wang and Bohua Zhong

Beijing Institute of Pharmacology and Toxicology, Beijing 100850, P. R. China


17-Allyl-4,5-anhydro-7α-[(R)-1-hydroxy-1-methyl-3-(2-thienyl)propyl]-6-methoxy-6,14-ethanomorphinan-3,4,5-triol (thienorphine 6) was synthesized and structurally characterized by NMR spectra, ESI-MS and X-ray diffraction. The crystal structure indicates that thienorphine maintained the main rigid structure of morphine while containing the C6-C14 ethano bridge. The allyl group is located in the equatorial position as expected. The packing diagram of 6 showed the presence of intramolecular and intermolecular O-H···O hydrogen bonds linking the molecules into a zigzag infinite quasi-one-dimensional chain structure.

Keywords: Oripavine derivatives; Morphine; Opioids; Thienorphine; Alkaloids; Thiophenes; Grignard reagents; Analgesics.

References: 32 live references.