Halogene

Sabetay, S.; Bléger, J.; Slawjanow, J. N.; Hahn, Fr. L.; Tomíček, O.; Jánsky, A. J.; Szancer, H.; Remington, Roe E.; Clendon, J. F.; Kolnitz, H. v.; Culp, F. B.; Roer, O.; Schuster, F.; Sontag, D.; Pavolini, T.; Palfray, L.

doi:10.1007/bf01376756

Cited by 1 publication

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“…Method B. 3-Hydroxy-17-aminophenalkylmorphinan (7)(8)(9)(10)(11)(12). The product (1.0 mmol) obtained from method A was dissolved in 1 N HCl-EtOH (10 mL) and shaken with 5% Pd/C (0.2 g) on a Parr hydrogenator at 45 psi of H2 for 3 h. The catalyst was separated by filtration and the solvent was removed in vacuo to give the crude HCI salt.…”

Section: Methodsmentioning

confidence: 99%

“…The conversion of 3-hydroxymorphinan6 to nitrophenalkyl intermediates 1-6 was carried out in DMF in the presence of K2C03 (method A). Catalytic reduction of the nitro group in HCl-EtOH (method B) gave the desired lV-(aminophenalkyl) -3-hydroxymorphinans 7-12. The formation of amide derivatives was achieved by treatment of the corresponding amines (7)(8)(9)(10)(11)(12) with the requisite acyl halide (method C). The maleimido compounds were obtained in three steps, the first being the reaction of amines 7-12 with maleic anhydride to form the corresponding maleamic acids.…”

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confidence: 99%

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3-Hydroxy-17-aralkylmorphinans as potential opiate receptor-site-directed alkylating agents

et al. 1977

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In an effort to develop opiate receptor-site-directed alkylating agents, a series of 3-hydroxy-17-aralkylmorphinans containing reactive groups was synthesized and tested for analgesic and opiate antagonist activity. Many of the target compounds exhibited the characteristics of agonists and, among this group, some were found to be active blockers of morphine analgesia. One of the more potent antagonists (41) was investigated further and it was found that while its action is specifically associated with opiate receptors, 41 could not be classified either as a competitive or noncompetitive antagonist in the classical sense. The duration of antagonist action in vivo of 41 and its in vitro receptor binding characteristics suggest that covalent association with opiate receptors is not not an important factor.

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