628325-62-2

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-Methylpiperazin-1-yl)benzaldehyde serves as a key intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drug candidates. Its presence in the molecular structure of potential medications allows for the exploration of its therapeutic applications across different medical fields.
Used in Medicinal Chemistry Research:
As a compound with potential biological activity, 3-(4-Methylpiperazin-1-yl)benzaldehyde is utilized in medicinal chemistry for research purposes. It is examined for its pharmacological effects, which may lead to the discovery of novel treatments and therapeutic interventions.
Used in Organic Synthesis:
3-(4-Methylpiperazin-1-yl)benzaldehyde is employed as a chemical intermediate in organic synthesis, facilitating the creation of diverse organic compounds. Its structural components make it a valuable building block for the development of complex organic molecules with specific applications in various industries.

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

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

Downstream Products

• 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 
• 628325-61-1 2-bromo-5-(4-methylpiperazin-1-yl)benzaldehyde 

Relevant academic research and scientific papers

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.

IMIDAZOPYRIDINES AS INHIBITORS OF AURORA KINASE AND/OR FLT3

The present invention relates to compounds of formula I: wherein R1 and R2 are as defined herein, or a pharmaceutically acceptable salt or solvate thereof. The compounds of formula I are inhibitors of aurora kinase and/or FLT3. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of proliferative disorders, such as cancer, as well as other diseases or conditions in which aurora kinase and/or FLT3 activity is implicated.

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.

Synthesis and characterization of Sant-75 derivatives as Hedgehog-pathway inhibitors

Sant-75 is a newly identified potent inhibitor of the hedgehog pathway. We designed a diversity-oriented synthesis program, and synthesized a series of Sant-75 analogues, which lays the foundation for further investigation of the structure-activity relationship of this important class of hedgehog-pathway inhibitors.

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.