Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 4: 3-Alkyl-4-halo-6-nitroquipazines

Byung Seok Moon; Byoung Se Lee; Dae Yoon Chi

doi:10.1016/j.bmc.2005.05.031

Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 4: 3-Alkyl-4-halo-6-nitroquipazines

Bioorg Med Chem. 2005 Aug 15;13(16):4952-9. doi: 10.1016/j.bmc.2005.05.031.

Authors

Byung Seok Moon¹, Byoung Se Lee, Dae Yoon Chi

Affiliation

¹ Department of Chemistry, Inha University, 253 Yonghyundong Namgu, Inchon 402-751, Republic of Korea.

PMID: 15993088
DOI: 10.1016/j.bmc.2005.05.031

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Binding, Competitive
Cerebral Cortex / metabolism
Citalopram / metabolism
Male
Quipazine / analogs & derivatives*
Quipazine / chemical synthesis
Quipazine / metabolism*
Rats
Rats, Sprague-Dawley
Selective Serotonin Reuptake Inhibitors / metabolism
Serotonin Antagonists / chemical synthesis*
Serotonin Antagonists / metabolism*
Structure-Activity Relationship
Synaptic Membranes / metabolism

Substances

Serotonin Antagonists
Serotonin Uptake Inhibitors
Citalopram
Quipazine
6-nitroquipazine