38941-29-6

Usage

Uses

Used in Pharmaceutical Synthesis:
4,5-dihydro-N-[(2-methylphenyl)methyl]-1H-Imidazol-2-amine is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure and reactivity allow for the creation of a wide range of drug molecules, contributing to the development of new treatments for various medical conditions.
Used in Agrochemical Production:
In the agrochemical industry, 4,5-dihydro-N-[(2-methylphenyl)methyl]-1H-Imidazol-2-amine is utilized as a precursor in the production of various agrochemicals. Its ability to form stable compounds makes it suitable for use in the development of pesticides and other agricultural chemicals that can enhance crop protection and yield.
Used in Drug Discovery and Development:
4,5-dihydro-N-[(2-methylphenyl)methyl]-1H-Imidazol-2-amine is also used as a starting material in drug discovery and development. Its potential pharmacological properties make it a promising candidate for further research and exploration, with the aim of identifying new therapeutic agents and advancing the field of medicinal chemistry.

Upstream product

• 96-45-7 N,N'-ethylenethiourea 
• 20112-79-2 2-methylthioimidazoline 
• 89-93-0 ortho-methylbenzylamine 
• 74-88-4 methyl iodide 
• 60546-77-2 methyl 2-(methylthio)-4,5-dihydro-1H-imidazole-1-carboxylate 

Downstream Products

• 1616632-77-9 11-benzyl-7-[(2-methylphenyl)methyl]-2,5,7,11-tetraazatricyclo[7.4.0.0^2,6]trideca-1⁽⁹⁾,5-dien-8-one 

Relevant academic research and scientific papers

Imidazo-pyrimidone Compounds, and Preparation Method and Application Thereof

Compounds of formula (I), imidazopyrimidine ketones, as well as preparations and applications thereof. Compounds and pharmaceutically acceptable salts thereof which stimulate the body to produce tumor necrosis factor-related apoptosis-inducing ligands, while avoiding the drawbacks of existing cancer treatments based on recombinant proteins and antibodies. Thus, they can provide novel options for the treatment of related tumors.

Ferrocene-containing Impiridone (ONC201) Hybrids: Synthesis, DFT modelling, in vitro evaluation, and structure–activity relationships

Inspired by the well-established clinical evidence about the interplay between apoptotic TRAIL (tumour necrosis factor-related apoptosis-inducing ligand) mechanism and reactive oxygen species (ROS)-mediated oxidative stress, a set of novel ONC201 hybrids containing the impiridone core and one or two differently positioned ferrocenylalkyl groups were synthesised in our present work. These two types of residues have been implicated in the aforementioned mechanisms associated with cytotoxic activity. A straightforward, primary amine-based synthetic approach was used allowing the introduction of a variety of N-substituents into the two opposite regions of the heterocyclic skeleton. Reference model compounds with benzyl and halogenated benzyl groups were also synthesised and tested. The in vitro assays of the novel impiridones on five malignant cell lines disclosed characteristic structure-activity relationship (SAR) featuring significant substituent-dependent activity and cell-selectivity. A possible contribution of ROS-mechanism to the cytotoxicity of the novel metallocenes was suggested by density functional theory (DFT)studies on simplified models. Accordingly, unlike the mono-ferrocenylalkyl-substituted products, the compounds containing two ferrocenylalkyl substituents in the opposite regions of the impiridone core display a much more pronounced long-term cytotoxic effect against A-2058 cell line than do the organic impiridones including ONC201 and ONC212. Furthermore, the prepared bis-metallocene derivatives also present substantial activity against COLO-205- and EBC-1 cell lines.

PHARMACOPHORE FOR TRAIL INDUCTION

There are disclosed imidazolinopyrimidinone compounds that have activity to induce TRAIL gene expression in macrophages. There is further disclosed a method for treating various cancers comprising administering effective amounts of an imidazolinopyrimidin

Pharmacophore reassignment for induction of the immunosurveillance cytokine TRAIL

Tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL) is an immunosurveillance cytokine that kills cancer cells but demonstrates little toxicity against normal cells. While investigating the TRAIL-inducing imidazolinopyrimidinone TIC10, a misassignment of its active structure was uncovered. Syntheses of the two isomers, corresponding to the published and reassigned structures, are reported. The ability of each to induce TRAIL expression in macrophages was investigated and it was found that only the compound corresponding to the reassigned structure shows the originally reported activity; the compound corresponding to the published structure is inactive. Importantly, this structural reassignment has furnished a previously unknown antitumor pharmacophore. Setting the record straight: An investigation of an imidazolinopyrimidinone (TIC10) reported to induce expression of the immunosurveillance cytokine TRAIL led to a constitutional reassignment of the active pharmacophore. Analysis of TRAIL induction in macrophages revealed the reported structure to be inactive. The structural identity of the active compound was established. The active compound was then synthesized and its activity confirmed.

METHODS OF TREATING ALPHA ADRENERGIC MEDIATED CONDITIONS

Described herein are compounds for and methods of treating conditions or diseases in a subject by administering to the subject a pharmaceutical composition containing an effective amount of an α-adrenergic modulator. The compounds and methods are also use