N-[omega-[4-(2-methoxyphenyl)-1-piperazinyl]alkyl]-2-quinolinamines as high-affinity fluorescent 5-HT1A receptor ligands.
We here report on the design, synthesis, binding affinities, and fluorescent properties of a series of serotonin 5-HT 1A receptor ligands, with N-[omega-[4-(2-methoxyphenyl)-1-piperazinyl]alkyl]-2-quinolinamine structure. Several of the new ligands displayed nanomolar affinity at 5-HT 1A receptor and good fluorescent properties. In particular, derivative 24 showed a favorable combination of 5-HT 1A receptor affinity ( K i = 0.4 nM), Stokes shift (excitation wavelength = 381 nm, emission wavelength = 455 nm), and quantum yield in ethanol (Phi = 0.45).
Lacivita
Enza
E
Dipartimento Farmaco-Chimico, Universita degli Studi di Bari, bari, Italy. lacivita@farmchim.uniba.it
Leopoldo
Marcello
M
D000634:Aminoquinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D054333:Drug Partial Agonism; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006168:Guinea Pigs; D007082:Ileum / Q000187:drug effects / Q000502:physiology; D066298:In Vitro Techniques; D008024:Ligands; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D058825:Serotonin 5-HT1 Receptor Agonists; D058829:Serotonin 5-HT1 Receptor Antagonists; D013329:Structure-Activity Relationship
C529301:6-amino-N-(2-(4-(2-methoxyphenyl)-1-piperazinyl)butyl)-2-quinolinamine; D000634:Aminoquinolines; D005456:Fluorescent Dyes; D008024:Ligands; D010879:Piperazines; D011804:Quinolines; D058825:Serotonin 5-HT1 Receptor Agonists; D058829:Serotonin 5-HT1 Receptor Antagonists