Dopamine quinone chemistry: a study of the influence of amide, amidine and guanidine substituents [-NH-CX-Y] on the mode of reaction.
The influence of N-substituents on the mode of reaction of ortho-quinones generated by oxidation of N-substituted dopamine derivatives has been studied. Ortho-quinones with amide, urea or guanidine side chains are relatively stable, with evidence of rearrangement to para-quinomethanes. The N-methylthiourea derivative rapidly cyclises giving a bicyclic product . The trichloromethylamidine derivative also rapidly cyclises but in this case gives a spirocyclic derivative . In contrast to the transient formation of spirocyclic products by other ortho-quinones derived from dopamine derivatives, e.g., , the product is stable and has been isolated and fully characterised.
Land
Edward J
EJ
Lennard-Jones Laboratories, School of Physical and Geographical Sciences, Keele University, Keele, Staffordshire ST55BG, UK.
Perona
Almudena
A
Ramsden
Christopher A
CA
Riley
Patrick A
PA
D000577:Amides / Q000737:chemistry; D000578:Amidines / Q000737:chemistry; D004298:Dopamine / Q000031:analogs & derivatives* / Q000737:chemistry; D004355:Drug Stability; D019791:Guanidine / Q000737:chemistry; D013329:Structure-Activity Relationship
D000577:Amides; D000578:Amidines; C104705:dopamine quinone; D019791:Guanidine; D004298:Dopamine