628325-62-2

Basic information

• Product Name: 3-(4-Methylpiperazin-1-yl)benzaldehyde
• Synonyms: Benzaldehyde, 3-(4-Methyl-1-piperazinyl)-
• CAS NO: 628325-62-2
• Molecular Formula: C₁₂H₁₆N₂O
• Molecular Weight: 204.2682
• Mol File: 628325-62-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 344.8 °C at 760 mmHg
• Flash Point: 151.1 °C
• Appearance: /
• Density: 1.107 g/cm³
• Vapor Pressure: 6.43E-05mmHg at 25°C
• Refractive Index: 1.581
• PKA: 7.68±0.42(Predicted)
• CAS DataBase Reference: 3-(4-Methylpiperazin-1-yl)benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-Methylpiperazin-1-yl)benzaldehyde(628325-62-2)
• EPA Substance Registry System: 3-(4-Methylpiperazin-1-yl)benzaldehyde(628325-62-2)

Safety Data

• Hazardous Substances Data: 628325-62-2(Hazardous Substances Data)

Usage

General Description

3-(4-Methylpiperazin-1-yl)benzaldehyde is a chemical compound with the molecular formula C14H18N2O. It is a benzaldehyde derivative containing a piperazine ring, which is a common structural motif in many pharmaceutical and medicinal compounds. This chemical is used as an intermediate in the synthesis of various organic compounds and pharmaceuticals. It is often utilized in drug discovery and development processes, specifically for the creation of potential drug candidates for various therapeutic applications. The compound may also have potential biological activity and pharmacological effects, making it of interest for further research and exploration in the medicinal chemistry field.

InChI:InChI=1/C12H16N2O/c1-13-5-7-14(8-6-13)12-4-2-3-11(9-12)10-15/h2-4,9-10H,5-8H2,1H3

Upstream product

• 3132-99-8 m-bromobenzoic aldehyde 
• 67437-93-8 2-(3-bromophenyl)-[1,3]dioxane 
• 109-01-3 1-methyl-piperazine 
• 17789-14-9 3-(1,3-dioxolan-2-yl)-phenylbromide 
• 75148-49-1 3-bromobenzaldehyde diethylacetal 

Downstream Products

• 628325-61-1 2-bromo-5-(4-methylpiperazin-1-yl)benzaldehyde 
• 1402709-74-3 3-((4-(6-chloro-2-(3-(4-methylpiperazin-1-yl)phenyl)-3H-imidazo[4,5-b]pyridin-7-yl)piperazin-1-yl)methyl)-5-methylisoxazole 

Relevant articles and documents

Design, synthesis and biological evaluation of chalcones as reversers of P-glycoprotein-mediated multidrug resistance

Overexpression of P-glycoprotein (P-gp) is one of the major causes for multidrug resistance (MDR), which has become a major obstacle in cancer therapy. One hopeful approach to reverse the MDR is to develop inhibitors of P-gp in expression and/or function. Here, we designed and synthesized a series of chalcone derivatives as P-gp inhibitors and evaluated their potential reversal activities against MDR. Among them, the most active compound MY3 had little intrinsic cytotoxicity and showed the highest activity (RF = 50.19) in reversing DOX resistance in MCF-7/DOX cells. Further studies demonstrated that MY3 could increase intracellular accumulation of DOX and inhibit expression of P-gp at mRNA and protein levels. More importantly, MY3 significantly enhanced the efficacy of DOX against the tumor xenografts bearing MCF-7/DOX cells with the precondition of unchanged body weight. Therefore, MY3 might represent a promising lead to develop MDR reversal agents for cancer chemotherapy.

Optimization of imidazo[4,5- b ]pyridine-based kinase inhibitors: Identification of a dual FLT3/aurora kinase inhibitor as an orally bioavailable preclinical development candidate for the treatment of acute myeloid leukemia

Optimization of the imidazo[4,5-b]pyridine-based series of Aurora kinase inhibitors led to the identification of 6-chloro-7-(4-(4-chlorobenzyl)piperazin- 1-yl)-2-(1,3-dimethyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridine (27e), a potent inhibitor of Aurora kinases (Aurora-A Kd = 7.5 nM, Aurora-B K d = 48 nM), FLT3 kinase (Kd = 6.2 nM), and FLT3 mutants including FLT3-ITD (Kd = 38 nM) and FLT3(D835Y) (Kd = 14 nM). FLT3-ITD causes constitutive FLT3 kinase activation and is detected in 20-35% of adults and 15% of children with acute myeloid leukemia (AML), conferring a poor prognosis in both age groups. In an in vivo setting, 27e strongly inhibited the growth of a FLT3-ITD-positive AML human tumor xenograft (MV4-11) following oral administration, with in vivo biomarker modulation and plasma free drug exposures consistent with dual FLT3 and Aurora kinase inhibition. Compound 27e, an orally bioavailable dual FLT3 and Aurora kinase inhibitor, was selected as a preclinical development candidate for the treatment of human malignancies, in particular AML, in adults and children.

Cationic chalcone antibiotics. Design, synthesis, and mechanism of action

This paper describes how the introduction of "cationic" aliphatic amino groups in the chalcone scaffold results in potent antibacterial compounds. It is shown that the most favorable position for the aliphatic amino group is the 2-position of the B-ring, in particular in combination with a lipophilic substituent in the 5-position of the B-ring. We demonstrate that the compounds act by unselective disruption of cell membranes. Introduction of an additional aliphatic amino group in the á-ring results in compounds that are selective for bacterial membranes combined with a high antibacterial activity against both Gram-positive and -negative pathogens. The most potent compound in this study (78) has an MIC value of 2 μM against methicillin resistant Staphylococus aureus.