Chemistry:Sulforidazine
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Sulforidazine (Imagotan, Psychoson, Inofal) a typical antipsychotic and a metabolite of thioridazine; it and mesoridazine are more potent than the parent compound, whose pharmacological effects are believed by some to be largely due to its metabolism into sulforidazine and mesoridazine.[1]
Synthesis
Sulforidazine can be synthesized starting 2-bromo-2'-amino-4'-methylsulfonyl-diphenyl sulfide (1).[2][3][4] Acetylation produces 2-bromo-2'-acetamino-4'-methylsulphonyl diphenylsulfide (2), which is then alkylated with 2-(2-chloroethyl)-1-methylpiperidine (3). Deacylation followed by a copper-catalyzed ring-formation reaction produces sulforidazine.
References
- ↑ "Greater potency of mesoridazine and sulforidazine compared with the parent compound, thioridazine, on striatal dopamine autoreceptors". The Journal of Pharmacology and Experimental Therapeutics 228 (3): 636–639. March 1984. doi:10.1016/S0022-3565(25)21884-5. PMID 6707914.
- ↑ "Sulforidazine". Thieme Pharmaceutical Substances. https://pharmaceutical-substances.thieme.com/lexicon/KD-19-0102?searchterm=sulforidazine&context=search.
- ↑ "Facile Syntheses of the Three Major Metabolites of Thioridazine". Helvetica Chimica Acta 88 (5): 962–967. 2005. doi:10.1002/hlca.200590089. Bibcode: 2005HChAc..88..962M.
- ↑ Bruschweiler C, Schwarb G, Winkler H, Renz J, "Heterocyclic compounds", US patent 3314948, issued 18 April 1967.
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