736991-52-9

Usage

Uses

Used in Pharmaceutical Industry:
2-PIPERAZIN-1-YL-BENZALDEHYDE is used as an intermediate in the synthesis of various pharmaceutical products for its potential role in the development of antipsychotic and analgesic drugs. It is valued for its contribution to the treatment of different medical conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 2-PIPERAZIN-1-YL-BENZALDEHYDE serves as an intermediate in the production of agrochemicals, leveraging its properties to enhance crop protection and management.
Used in Antibacterial and Antimicrobial Applications:
2-PIPERAZIN-1-YL-BENZALDEHYDE is utilized for its antibacterial and antimicrobial properties, making it a candidate for applications that require the inhibition of microbial growth in various settings.
Used in Material Science:
2-PIPERAZIN-1-YL-BENZALDEHYDE is also considered in material science for its potential use in the synthesis of novel materials, where its unique structure may contribute to the development of new material properties.
Used in Organic Chemistry:
2-PIPERAZIN-1-YL-BENZALDEHYDE is employed as a building block in organic chemistry, where it can be used to construct more complex organic molecules for a variety of applications.

InChI:InChI=1/C11H14N2O/c14-9-10-3-1-2-4-11(10)13-7-5-12-6-8-13/h1-4,9,12H,5-8H2

Upstream product

• 111373-03-6 2-(piperazin-1-yl)benzonitrile 
• 110-85-0 piperazine 
• 446-52-6 2-Fluorobenzaldehyde 
• 174855-57-3 tert-butyl 4-(2-formylphenyl)piperazinecarboxylate 

Downstream Products

• 174855-57-3 tert-butyl 4-(2-formylphenyl)piperazinecarboxylate 
• 748808-82-4 4-{(2R)-[(3R)-1,2,3,4-tetrahydroisoquinolinylcarboxamido]-3-(4-chlorophenyl)propionyl}-1-[2-formylphenyl]piperazine 
• 865303-23-7 {1-(4-chloro-benzyl)-2-[4-(2-formyl-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Aromatic-ring azacyclo derivatives and application thereof

Aromatic-ring azacyclo derivatives and an application thereof are provided. The invention relates to compounds represented by the formula (V), and a preparation method and an application thereof in medicines. In particular, the invention relates to derivatives of the compounds represented by the general formula (V), and a preparation method and the application thereof as therapeutic agents in prevention and treatment of hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, hepatic steatosis, type-II diabetes, hyperglycemia, obesity or insulin resistance syndromes and metabolic syndromes. The compounds disclosed by the invention also can reduce total cholesterol, LDL-cholesterol and triglycerides, increase the expression of hepatic LDL receptors and inhibit the expression of PCSK9.

Optimization of piperazinebenzylamines with a N-(1-methoxy-2-propyl) side chain as potent and selective antagonists of the human melanocortin-4 receptor

Piperazinebenzylamines bearing a small N-(1-methoxy-2-propyl) side chain were found to be potent and selective antagonists of the human melanocortin-4 (MC4) receptor. Compound 7b, having Ki values of 6.9 and 2800 nM at the human MC4 and MC3 receptors, respectively, has moderate oral bioavailability in mice, which is improved relative to the arylethyl analogues.

Structure-activity relationships of piperazinebenzylamines as potent and selective agonists of the human melanocortin-4 receptor

SAR studies on a series of piperazinebenzenes directed toward the human melanocortin-4 receptor resulted in potent MC4R agonists. Replacement of the triazole moiety of an initial lead 4 by a basic nitrogen baring a lipophilic side-chain increased the binding affinities of these compounds. Analogs bearing an additional hetero-atom in the side-chain possessed good agonist potency. Thus, 11h had a Ki of 11 nM, and 13g exhibited an EC50 of 3.8 nM and a Ki of 6.4 nM.

Piperazinebenzylamines as potent and selective antagonists of the human melanocortin-4 receptor

SAR studies of a series of piperazinebenzylamines resulted in the discovery of potent antagonists of the human melanocortin-4 receptor. Compounds 11c, 11d, and 11l, which had Ki values of 21, 14, and 15 nM, respectively, possessed low efficacy

4-{(2R-[3-Aminopropionylamido]-3-(2,4-dichlorophenyl)propionyl} -1-{2-[(2-thienyl)ethylaminomethyl]phenyl}piperazine as a potent and selective melanocortin-4 receptor antagonist - Design, synthesis, and characterization

Recent studies have demonstrated that melanocortin-4 receptor (MC4R) antagonists can prevent weight loss in tumor-bearing mice, which indicates clinical usage for the treatment of cachexia. In our efforts to develop potent and selective antagonists of the human MC4R, we designed piperazinebenzylamines bearing a 2,4-dichlorophenylalanine, by utilizing information derived from structure-activity relationships of MC4R agonists and mutagenesis results of the MC4R and peptide ligands. On the basis of known MC4R agonists such 6, we successfully synthesized potent MC4R antagonists exemplified by 10, which possesses a Ki value of 1.8 nM in binding affinity. 10 does not stimulate cAMP release in HEK 293 cells expressing the human MC4 receptor at 10 μM concentration. It was demonstrated by Schild analysis that 10 was a competitive functional antagonist with a pA2 value of 7.9 in the inhibition of α-MSH-stimulated cAMP accumulation. 10 also penetrated into the brain when dosed intravenously in rats.

Synthesis and Structure-Activity Relationships of Novel Arylpiperazines as Potent and Selective Agonists of the Melanocortin Subtype-4 Receptor

The melanocortin receptors have been implicated as potential targets for a number of important therapeutic indications, including inflammation, sexual dysfunction, and obesity. We identified compound 1, an arylpiperazine attached to the dipeptide H-D-Tic-D-p-Cl-Phe-OH, as a novel melanocortin subtype-4 receptor (MC4R) agonist through iterative directed screening of nonpeptidyl G-protein-coupled receptor biased libraries. Structure-activity relationship (SAR) studies demonstrated that substitutions at the ortho position of the aryl ring improved binding and functional potency. For example, the o-isopropyl-substituted compound 29 (Ki = 720 nM) possessed 9-fold better binding affinity compared to the unsubstituted aryl ring (Ki = 6600 nM). Sulfonamide 39 (Ki = 220 nM) fills this space with a polar substituent, resulting in a further 2-fold improvement in binding affinity. The most potent compounds such as the diethylamine 44 (Ki = 60 nM) contain a basic group at this position. Basic heterocycles such as the imidazole 50 (Ki = 110 nM) were similarly effective. We also demonstrated good oral bioavailability for sulfonamide 39.