A Catechol Receptor Model by Macrocyclic Polyamines

Article abstract of DOI:10.1021/ja00345a066

18-Azacrown-6 (L) (as triprotonated species) has been shown to form stable 1:1 complexes with catechol (1) and its biological derivatives 2-8 in neutral pH solutions.Their stability constants β_L were determined polarographically.The catechol receptor model L interacts with Dopa and dopamine with a similar order of β_L to indicate that the residual donor groups on the catecholamines do not significantly contribute to the complex formation.L has similar affinities to methyl ether derivatives of catechols.Further, L associates with an adrenergic blocking agent, dichloroisoproterenol (10).It also recognizes other drugs or drug functions such as resorcinol (9), tropolone (11), salicylic acid (12), p-aminosalicylic acid (13), and α-picolinic acid (14).