35345-09-6

Usage

Heterocyclic compound

Imidazole ring system The compound contains a ring structure made up of both carbon and nitrogen atoms, which is characteristic of imidazole.

Methyl group attachment

4th carbon atom A methyl group (CH3) is attached to the fourth carbon atom of the imidazole ring, which influences its chemical properties and reactivity.

Chlorophenyl group

Phenyl ring with a chlorine substituent The compound features a phenyl ring (a six-carbon ring structure) with a chlorine atom attached to it, which contributes to its unique properties and potential applications.

Potential applications

Pharmaceutical and chemical industries Due to its unique structure and properties, 2-(4-CHLOROPHENYL)-4-METHYL-3H-IMIDAZOLE may be used in the synthesis of other organic compounds or as a starting material for new pharmaceutical drug development.

Biological activities

Relevance in drug discovery and development The compound may possess biological activities that make it relevant for research in drug discovery and development, potentially leading to new therapeutic agents.

InChI:InChI=1/C10H9ClN2/c1-7-6-12-10(13-7)8-2-4-9(11)5-3-8/h2-6H,1H3,(H,12,13)

Upstream product

• 623-03-0 4-Cyanochlorobenzene 
• 41282-40-0 but-2-ynylamine 
• 23328-88-3 2-bromo-4-methyl-1H-imidazole 
• 1679-18-1 4-Chlorophenylboronic acid 

Relevant academic research and scientific papers

Discovery of Imidazole-Based Inhibitors of Plasmodium falciparum cGMP-Dependent Protein Kinase

The discovery of new targets for the treatment of malaria, in particular those aimed at the pre-erythrocytic stage in the life cycle, advanced with the demonstration that orally administered inhibitors of Plasmodium falciparum cGMP-dependent protein kinase (PfPKG) could clear infection in a murine model. This enthusiasm was tempered by unsatisfactory safety and/or pharmacokinetic issues found with these chemotypes. To address the urgent need for new scaffolds, this paper presents initial structure-activity relationships in an imidazole scaffold at four positions, representative in vitro ADME, hERG characterization, and cell-based antiparasitic activity. This series of PfPKG inhibitors has good in vitro PfPKG potency, low hERG activity, and cell-based antiparasitic activity against multiple Plasmodium species that appears to be correlated with the in vitro potency.

Atom-economical synthesis of N-heterocycles via cascade inter-/intramolecular C-N Bond-forming reactions catalyzed by Ti amides

Direct and efficient catalytic reactions with excellent regioselectivity for the preparation of a series of substituted isoindoles, isoquinolines, and imidazoles are reported. Reaction of C6H4(2-CN)C≡C-R with an array of amines, catalyzed by 10 mol % of [σ:η1: η5-(OCH2)(Me2NCH2)C 2B9H9]Ti(NMe2) (1), gives a series of substituted isoindoles in very high yields. In a similar manner, interaction of C6H4(2-CH2CN)C≡C-Ph with various kinds of amines affords a wide range of substituted isoquinolines. On the other hand, treatment of propargylamines (R′C≡CCH2NHR′′) with nitriles in the presence of 10 mol % of 1 produces a class of substituted imidazoles in high yields. A possible reaction mechanism is proposed, involving sequential inter- and intramolecular C-N bond formation via hydroamination/ cyclization reaction of cyanoalkynes with amines or nitriles with propargylamines catalyzed by titanium amides.