60546-77-2

Usage

Uses

Used in Pharmaceutical Industry:
4,5-Dihydro-2-(Methylthio)-1H-iMidazole-1-carboxylic Acid Methyl Ester is used as a chemical intermediate for the synthesis of substituted imidazolidinethiones and thioimidazolines, which are important compounds in the development of pharmaceutical drugs. These synthesized compounds have potential applications in treating various medical conditions, such as bacterial infections and other diseases.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4,5-Dihydro-2-(Methylthio)-1H-iMidazole-1-carboxylic Acid Methyl Ester is utilized as a versatile building block for the creation of a wide range of organic compounds. Its unique structure allows for various chemical reactions, enabling the formation of new molecules with different properties and potential applications in various industries.
Used in Research and Development:
4,5-Dihydro-2-(Methylthio)-1H-iMidazole-1-carboxylic Acid Methyl Ester is also employed in research and development settings, where scientists and chemists explore its potential applications and properties. 4,5-Dihydro-2-(Methylthio)-1H-iMidazole-1-carboxylic Acid Methyl Ester can be used to study the synthesis of new molecules, investigate its reactivity with other chemicals, and understand its potential uses in various fields, such as materials science, pharmaceuticals, and agrochemicals.

Upstream product

• 59863-98-8 methyl 2-thioxoimidazolidine-1-carboxylate 
• 74-88-4 methyl iodide 
• 5464-11-9 2-methylthio-2-imidazoline hydroiodide 
• 79-22-1 methyl chloroformate 
• 96-45-7 N,N'-ethylenethiourea 

Downstream Products

• 1222500-08-4 6-(diphenylphosphino)-N-(imidazolidin-2-ylidene)pyridin-2-amine 
• 1222500-06-2 3-(diphenylphosphino)-N-(imidazolidin-2-ylidene)aniline 
• 1222500-11-9 1-(3-(diphenylphosphino)phenyl)-N-(imidazolidin-ylidene)methanamine 
• 38941-29-6 N-(2-methylbenzyl)-4,5-dihydro-1H-imidazol-2-amine 

Relevant academic research and scientific papers

SYNTHESIS OF NOVEL IMIPRIDONE DERIVATIVES AND THEIR EVALUATION FOR THEIR ANTICANCER ACTIVITY

The present invention relates to compounds of formula (I) (I) or pharmaceutically acceptable salts, and stereoisomers thereof, including enantiomers, racemic mixtures, mixtures of enantiomers, or combinations thereof, which are applicable for use in treating cancer diseases. The present invention further relates to a pharmaceutical composition comprising the above compounds.

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.

C-N Bond forming reactions in the synthesis of substituted 2-aminoimidazole derivatives

Carbon-nitrogen bond forming reactions oriented to the synthesis of 2-amino-imidazolidines and imidazoles have been investigated. The C-2 amination of imidazolidinones, via the corresponding 2-chlorodihydroimidazoles, led to 2-benzylaminodihydroimidazole or bis(dihydroimidazole)amino derivatives by choosing the adequate experimental conditions. On the other hand, the use of N-acyl-2-methylsulfanyldihydroimidazoles allowed carrying out the reactions with aromatic amines, such as p-anisidine. Finally, palladium catalyzed Buchwald- Hartwig amination was the method of choice for C-N coupling between 2-haloimidazoles and aromatic amines in the synthesis of the corresponding imidazoles.

Transition-state stabilization by a secondary substrate-ligand interaction: A new design principle for highly efficient transition-metal catalysis

A library of monodentate phosphane ligands, each bearing a guanidine receptor unit for carboxylates, was designed. Screening of the library gave some excellent catalysts for regioselective hydroformylation of ss,γ- unsaturated carboxylic acids. A terminal alkene, but-3-enoic acid, was hydroformylated with a linear/branched (l/b) regioselectivity up to 41. An internal alkene, pent-3-enoic acid was hydroformylated with regioselectivity up to 18:1. Further substrate selectivity (e.g., acid vs. methyl ester) and reaction site selectivity (monofunctionalization of 2- vinylhept-2-enoic acid) were also achieved. Exploration of the structure-activity relationship and a practical and theoretical mechanistic study gave us an insight into the nature of the supramolecular guanidinium-carboxylate interaction within the catalytic system. This allowed us to identify a selective transition-state stabilization by a secondary substrate-ligand interaction as the basis for catalyst activity and selectivity.

Methods of making 6-[(4,5-Dihydro-1H-imidazol-2-yl)amino-]-7-methyl-1H-benzimidazole-4-carbonitrile and its preferred salt form

6-[(4,5-Dihydro-1H-imidazol-2-yl)amino-]-7-methyl-1H-benzimidazole-4-carbonitrile substantially free of 2,3,7-triamino-4,6-dimethyl-1,9-phenazinedicarbonitrile, and the anhydrous monoacetate salt thereof, are useful in the treatment of alpha-2 mediated di

A novel method for the efficient synthesis of 2-arylamino-2-imidazolines

A novel method for the efficient synthesis of 2-arylamino-2-imidazolines is described. (C) 2000 Elsevier Science Ltd.

The Reaction of Imidazolidine-2-thione with Carbon Disulphide

The reaction of imidazolidine-2-thione (ethylenethiourea) with carbon disulphide in the presence of strong bases was investigated.The use of sodium hydride as base afforded 1,2-bis-ethane (6) and 2,3,6,7-tetrahydrodi-imidazothiadiazine-5-thione (8).On the other hand, reaction using n-butyl-lithium, followed by methylation, gave a dimethylated compound, methyl 2-methylthio-4,5-dihydroimidazole-1-carbodithioate (11).