Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 4: 3-Alkyl-4-halo-6-nitroquipazines.
On the basis of the structure-activity relationship (SAR) of 4-chloro-6-nitroquipazine (Ki = 0.03 nM) and 3-fluoropropyl-6-nitroquipazine (Ki = 0.32 nM), 3-alkyl-4-halo-6-nitroquipazines were synthesized and tested for their potential abilities in vitro to displace [3H]citalopram binding to the rat cortical membranes. Binding affinities of 3b and 4d were Ki = 2.70+/-0.32 and 2.23+/-0.46 nM, respectively. The syntheses of 3-alkyl-4-halo-6-nitroquipazine, their in vitro binding affinities, and the SAR of C3, C4 position in 6-nitroquipazine are described.
Department of Chemistry, Inha University, 253 Yonghyundong Namgu, Inchon 402-751, Republic of Korea.
Byung Seok
BS
Moon
Byoung Se
BS
Lee
Dae Yoon
DY
Chi
D000818:Animals; D001667:Binding, Competitive; D002540:Cerebral Cortex / Q000378:metabolism; D015283:Citalopram / Q000378:metabolism; D008297:Male; D011814:Quipazine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism*; D051381:Rats; D017207:Rats, Sprague-Dawley; D012702:Serotonin Antagonists / Q000138:chemical synthesis* / Q000378:metabolism*; D017367:Selective Serotonin Reuptake Inhibitors / Q000378:metabolism; D013329:Structure-Activity Relationship; D013570:Synaptic Membranes / Q000378:metabolism
D015283:Citalopram; D011814:Quipazine; D012702:Serotonin Antagonists; D017367:Selective Serotonin Reuptake Inhibitors; C031227:6-nitroquipazine