769099-80-1

Usage

Molecular structure

2-(4-FLUOROBENZYL)-2,5-DIAZA-BICYCLO[2.2.1]HEPTANE is a bicyclic amine derivative that contains a 2,5-diazabicyclo[2.2.1]heptane skeleton with a fluorobenzyl substitution at the 2-position.

Classification

It belongs to the class of heterocyclic compounds.

Potential use

It has been studied for its potential as a monoamine reuptake inhibitor and has shown promise in the treatment of disorders such as depression, anxiety, and obsessive-compulsive disorder.

Research tool

It is also used as a research tool in neuroscience for studying the serotonergic system and its role in psychiatric disorders.

InChI:InChI=1/C12H15FN2/c13-10-3-1-9(2-4-10)7-15-8-11-5-12(15)6-14-11/h1-4,11-12,14H,5-8H2

Upstream product

• 132339-20-9 <1R,4R>-(1R-cis) 2,5-diazabicyclo<2.2.2>octane 
• 459-57-4 4-fluorobenzaldehyde 
• 198989-07-0 tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate 

Relevant academic research and scientific papers

hERG optimizations of IMB1603, discovery of alternative benzothiazinones as new antitubercular agents

IMB1603, a new benzothiazinone lead discovered by our lab, exhibited potent anti-MTB activity in vitro and in vivo, but significant hERG binding potency (IR > 90% at 10 μM). Thus, we embarked on a lead optimization program with the goal of identifying alternative leads that could reduce the hERG liability without sacrificing antimycobacterial potency. Compounds 2c and 4c were identified to maintain the anti-MTB activity (MICs 0.035–0.078 μM), and had lower hERG binding affinity (IR 50% at 10 μM). Both of them were also found to have acceptable safety and pharmacokinetic properties. Studies to determine the in vivo efficacy of 2c and 4c are currently underway.

Design, synthesis, and biological evaluation of novel 2-methylpiperazine derivatives as potent CCR5 antagonists

Three series of novel 2-methylpiperazine derivatives were designed and synthesized using a fragment-assembly strategy. Among them, six compounds (13, 16, 18, 22, 33, and 36) showed potent activity against CCR5 comparable to that of the positive control, maraviroc, in calcium mobilization assay. Moreover, some compounds were selected and further tested for their antiviral activity in HIV-1 single cycle assay. As a result, four compounds (13, 16, 33, and 36) showed antiviral activity at the nanomolar level. Additionally, the potent four compounds showed no cytotoxicity at a concentration of 10 μM.