(E)-(methyloxyimino)acetamides as analogues of neuroleptic benzamides: synthesis and D2-dopaminergic binding affinity.
Some type C (E)-(methyloxyimino)acetamides were synthesised as analogues of type A neuroleptic and antipsychotic benzamides, in which the aromatic group is substituted by a methyloxyiminomethyl moiety with the E configuration (CH2ON = CH, E-MOIMM). Type C compounds were tested for their D2-dopaminergic binding affinity in order to obtain an indication of their potential neuroleptic and antipsychotic properties. Biological results showed that only a few aryl-substituted E-MOIM derivatives possess a certain affinity for the D2-dopaminergic receptor, at least one order of magnitude lower than that of metoclopramide and sulpiride.
Lapucci
A
A
Dipartimento di Scienze Farmaceutiche, Università di Pisa, Italy.
Macchia
M
M
Orlandini
E
E
Romagnoli
F
F
Rossello
A
A
Chiellini
G
G
Cozzini
P
P
Domiano
P
P
D000081:Acetamides / Q000138:chemical synthesis* / Q000378:metabolism; D000818:Animals; D014150:Antipsychotic Agents / Q000737:chemistry*; D018360:Crystallography, X-Ray; D018492:Dopamine Antagonists / Q000494:pharmacology; D066298:In Vitro Techniques; D008787:Metoclopramide / Q000494:pharmacology; D017072:Neostriatum / Q000187:drug effects / Q000378:metabolism; D010091:Oximes / Q000138:chemical synthesis* / Q000378:metabolism; D011869:Radioligand Assay; D017448:Receptors, Dopamine D2 / Q000187:drug effects / Q000378:metabolism*; D013469:Sulpiride / Q000494:pharmacology; D013552:Swine
D000081:Acetamides; D014150:Antipsychotic Agents; D018492:Dopamine Antagonists; D010091:Oximes; D017448:Receptors, Dopamine D2; D013469:Sulpiride; D008787:Metoclopramide