66307-58-2

Usage

InChI:InChI=1/C19H24N2O/c1-3-8-18(9-4-1)21-15-13-20(14-16-21)12-7-17-22-19-10-5-2-6-11-19/h1-6,8-11H,7,12-17H2

Upstream product

• 92-54-6 4-phenyl-1-piperazine 
• 3384-04-1 3-chloropropyl phenyl ether 
• 119967-33-8 3-phenoxypropyl methanesulfonate 
• 108-95-2 phenol 
• 1746-13-0 allyl phenyl ether 
• 6180-61-6 3-phenoxypropanol 
• 10599-17-4 1-(3-chloropropyl)-4-phenylpiperazine 

Relevant academic research and scientific papers

Multi-receptor drug design: Haloperidol as a scaffold for the design and synthesis of atypical antipsychotic agents

Using haloperidol as a scaffold, new agents were designed to investigate the structural contributions of various groups to binding at CNS receptors associated with atypical antipsychotic pharmacology. It is clear that each pharmacophoric group, the butyrophenone, the piperidine and the 4-chlorophenyl moieties contributes to changes in binding to the receptors of interest. This strategy has resulted in the identification of several new agents, compounds 16, 18, 19, 23, 24 and 25, with binding profiles which satisfy our stated criteria for agents to act as potential atypical antipsychotics. This research demonstrates that haloperidol can serve as a useful lead in the identification and design of new agents that target multiple receptors associated with antipsychotic pharmacology.

Discovery of LASSBio-772, a 1,3-benzodioxole N-phenylpiperazine derivative with potent alpha 1A/D-Adrenergic receptor blocking properties

We described herein the discovery of 1-(2-(benzo[d] [1,3]dioxol-6-yl)ethyl) -4-(2-methoxyphenyl) piperazine (LASSBio-772), as a novel potent and selective alpha 1A/1D adrenoceptor (AR) antagonist selected after screening of functionalized N-phenylpiperazine derivatives in phenylephrine-induced vasoconstriction of rabbit aorta rings. The affinity of LASSBio-772 for alpha 1A and alpha 1B AR subtypes was determined through displacement of [ 3H]prazosin binding. We obtained Ki values of 0.14 nM for the alpha 1A-AR, similar to that displayed by tamsulosin (Ki = 0.13 nM) and 5.55 nM for the alpha 1B-AR, representing a 40-fold higher affinity for alpha 1A-AR. LASSBio-772 also presented high affinity (KB = 0.025 nM) for the alpha 1D-AR subtype in the functional rat aorta assay, showing to be equipotent to tamsulosin (KB = 0.017 nM).

The Synthesis and Antiallergy Activity of 1-(Aryloxy)-4-(4-arylpiperazinyl)-2-butanol Derivatives

A series of 1-(aryloxy)-4-(4-arylpiperazinyl)-2-butanol derivatives were prepared and evaluated for antiallergy activity in the passive foot anaphylaxis (PFA) assay in rats.Twenty-seven derivatives had activity equal to or greater than the parent, α-(phen

Synthesis and Biological Activities of 3-Substituted 1-Aryloxyaminopropanes

A number of 3-substituted 1-aryloxyaminopropanes (9-43) have been prepared by the reaction of appropriate hydroxyaryl compound with 1-chloro-3-1-(N4-aryl-piperazinyl/piperidinyl)>propanes (1-8).The 1-(6/7-quinolyloxy)-3-substituted

3-Tertiary amino-1-aryloxy- or aryl-propanes and -propan -2-ols and some related compounds

The synthesis and pharmacological activity of some 3 tertiary amino 1 aryloxy or 1 aryl, 1 thiophenoxy and 1 anilino propan 2 ols and propanes, particularly those derived from N phenylpiperazines are described. Effect of substituents (nature/position) on the phenyl ring, the phenoxy ring as well as alteration in the hydroxylic function vis a vis the structure activity relationships (SAR) are discussed. In general, the 1 aryloxy compounds have hypotensive activity this being more pronounced in those carrying an o substituent on the phenyl ring, while m and p substituted derivatives have their effect primarily on the CNS. Variations in the phenoxy moiety do not significantly alter the intrinsic activity. The 1 aryl compounds, on the other hand, have significant CNS activity, which is markedly affected by the substituents on the 1 aryl residue.