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All posts Subject: Sulfur isostere of the Opiate IsoLevorphanol Please login to post

Rhodium
(Chief Bee)
11-30-03 01:12
No 473817
User Picture Sulfur isostere of the Opiate IsoLevorphanol
(Rated as: good read)

Synthesis and crystal structure of 17-deaza-17-methyl thionium isomorphinan (isosulforphanol) perchlorate, an isostere of the opiate isolevorphanol
Bernard Belleau, Ugo Gulini, Barbara Gour-Salin, F. R. Ahmed
Can. J. Chem. 63, 1268 (1985) (https://www.rhodium.ws/pdf/isosulforphanol.pdf)

Abstract
No morphinan analog carrying a heteroatom other than nitrogen at position 17 has yet been synthesized. The synthesis of the position 17 sulfur analog of the perchlorate salt of (±)-isolevorphanol is described. The strategy adopted is based on the classical Grewe synthesis of morphinans and, under narrowly defined conditions, the title compound isosulforphanol (3a) and an intermediate by-product 13 resulting from an unusual non-bridged head ring closure of 11a were obtained. The X-ray structures of both 3a and 13 were determined. Crystals of 13 are monoclinic. The crystals of 3a are orthorhombic. The C₁₇H₂₃OS⁺ molecule has been identified by this X-ray analysis as S-methyl isosulforphanol (Fig. 2). The structure of 13 is shown in Fig. 1. The stereochemical outcome of the Grewe-like synthesis is thus established as proceeding in a reversed manner when sulfur replaces the nitrogen in the final cyclization step. Preliminary pharmacological studies showed that 3a is a potent agonist in the central nervous system but a potent antagonist on the guinea-pig ileum.

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		Rhodium (Chief Bee) 11-30-03 01:12 No 473817				Sulfur isostere of the Opiate IsoLevorphanol (Rated as: good read)
						Synthesis and crystal structure of 17-deaza-17-methyl thionium isomorphinan (isosulforphanol) perchlorate, an isostere of the opiate isolevorphanol Bernard Belleau, Ugo Gulini, Barbara Gour-Salin, F. R. Ahmed Can. J. Chem. 63, 1268 (1985) (https://www.rhodium.ws/pdf/isosulforphanol.pdf) Abstract No morphinan analog carrying a heteroatom other than nitrogen at position 17 has yet been synthesized. The synthesis of the position 17 sulfur analog of the perchlorate salt of (±)-isolevorphanol is described. The strategy adopted is based on the classical Grewe synthesis of morphinans and, under narrowly defined conditions, the title compound isosulforphanol (3a) and an intermediate by-product 13 resulting from an unusual non-bridged head ring closure of 11a were obtained. The X-ray structures of both 3a and 13 were determined. Crystals of 13 are monoclinic. The crystals of 3a are orthorhombic. The C₁₇H₂₃OS⁺ molecule has been identified by this X-ray analysis as S-methyl isosulforphanol (Fig. 2). The structure of 13 is shown in Fig. 1. The stereochemical outcome of the Grewe-like synthesis is thus established as proceeding in a reversed manner when sulfur replaces the nitrogen in the final cyclization step. Preliminary pharmacological studies showed that 3a is a potent agonist in the central nervous system but a potent antagonist on the guinea-pig ileum.

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