Synthesis and Tritium Labelling of 6β‐Amino‐4,5α‐epoxymorphinans and their 14‐hydroxy derivatives as potential affinity labelling probes with μ opioid agonist activity

The synthesis of 6β-(methylfumaramido) and 6β-chloroacetamido derivatives 1b and 1c of 6β-amino-7,8- didehydromorphinan and the corresponding 14-hydroxy derivatives 1e and 1f are described. The 7,8-dihydro derivatives of these compounds were synthesized in inactive (2b,c,e,f) as well as in tritiated form (3b,c,e,f).

[1]  S. Hosztafi,et al.  Applicaltion of the Mitsunobu reaction in the morphine series. Preparation of 6β-amino-14β-hydroxymorphine and 14-hydroxycodeine derivatives , 1994 .

[2]  S. Hosztafi,et al.  Stereoselective synthesis of β-naltrexol, β-naloxol β-naloxamine, β-naltrexamine and related compounds by the application of the mitsunobu reac , 1994 .

[3]  S. Hosztafi,et al.  Application of the Mitsunobu Reaction for Morphine Compounds. Preparation of 6β-Aminomorphine and Codeine Derivatives , 1992 .

[4]  R. Tallarida,et al.  Studies on kinetics of [3H]beta-funaltrexamine binding to mu opioid receptor. , 1990, Molecular pharmacology.

[5]  S. Archer,et al.  Affinity labeling of mu opioid receptors by sulfhydryl alkylating derivatives of morphine and morphinone. , 1990, Molecular pharmacology.

[6]  L. Liu-Chen,et al.  Covalent labeling of mu opioid binding site by [3H]beta-funaltrexamine. , 1987, Molecular pharmacology.

[7]  P. Portoghese,et al.  Nonequilibrium opioid antagonist activity of 6,14-dideoxynaltrexone derivatives. , 1987, Journal of medicinal chemistry.

[8]  P. Portoghese,et al.  Irreversible blockage of opioid receptor types by ester homologues of beta-funaltrexamine. , 1986, Journal of medicinal chemistry.

[9]  P. Portoghese,et al.  Affinity labels for opioid receptors. , 1985, Annual review of pharmacology and toxicology.

[10]  D. L. Larson,et al.  IMPORTANCE OF CARBON 6 CHIRALITY IN CONFERRING IRREVERSIBLE OPIOID ANTAGONISM TO NALTREXONE-DERIVED AFFINITY LABELS , 1984 .

[11]  D. L. Larson,et al.  Importance of C-6 chirality in conferring irreversible opioid antagonism to naltrexone-derived affinity labels. , 1983, Journal of medicinal chemistry.

[12]  P. Portoghese,et al.  Stereospecific synthesis of the 6.alpha.- and 6.beta.-amino derivatives of naltrexone and oxymorphone , 1980 .

[13]  D. L. Larson,et al.  A novel opioid receptor site directed alkylating agent with irreversible narcotic antagonistic and reversible agonistic activities. , 1980, Journal of medicinal chemistry.

[14]  D. L. Larson,et al.  Chloroxymorphamine, and opioid receptor site-directed alkylating agent having narcotic agonist activity. , 1979, Science.

[15]  D. L. Larson,et al.  Synthesis and pharmacologic characterization of an alkylating analogue (chlornaltrexamine) of naltrexone with ultralong-lasting narcotic antagonist properties. , 1979, Journal of medicinal chemistry.

[16]  R. Hanson,et al.  Stereochemical studies on medicinal agents. 23. Synthesis and biological evaluation of 6-amino derivatives of naloxone and naltrexone. , 1977, Journal of Medicinal Chemistry.

[17]  M. Wilchek,et al.  [11] Haloacetyl derivatives , 1977 .

[18]  G. W. Anderson,et al.  A reinvestigation of the mixed carbonic anhydride method of peptide synthesis. , 1967, Journal of the American Chemical Society.

[19]  G. W. Anderson,et al.  Racemization Control in the Synthesis of Peptides by the Mixed Carbonic-Carboxylic Anhydride Method , 1966 .

[20]  J. R. Vaughan,et al.  The Preparation of Peptides Using Mixed Carbonic—Carboxylic Acid Anhydrides , 1952 .