114834-03-6

Basic information

• Product Name: 2-chloro-4-(1H-imidazol-1-yl)pyrimidine
• Synonyms: 2-chloro-4-(1H-imidazol-1-yl)pyrimidine
• CAS NO: 114834-03-6
• Molecular Formula: C₇H₅ClN₄
• Molecular Weight: 180.5944
• Product Categories: Pyrazines, Pyrimidines & Pyridazines;Halides;Pyrazines, Pyrimidines & Pyridazines
• Mol File: 114834-03-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-chloro-4-(1H-imidazol-1-yl)pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-4-(1H-imidazol-1-yl)pyrimidine(114834-03-6)
• EPA Substance Registry System: 2-chloro-4-(1H-imidazol-1-yl)pyrimidine(114834-03-6)

Safety Data

• Hazardous Substances Data: 114834-03-6(Hazardous Substances Data)

Usage

General Description

2-Chloro-4-(1H-imidazol-1-yl)pyrimidine, also known as Cl-IMPY, is a chemical compound with the molecular formula C6H5ClN4. It is an imidazole-based heterocyclic compound that contains a chloro and pyrimidine group. 2-chloro-4-(1H-imidazol-1-yl)pyrimidine is widely used in the pharmaceutical industry for the synthesis of various pyrimidine-based drugs and pharmaceuticals. Additionally, Cl-IMPY has shown potential as an antifungal and antimicrobial agent, with research being conducted on its potential use in the treatment of various fungal infections. It is also used as a precursor in the synthesis of various other chemical compounds due to its versatile reactivity and functional groups.

Upstream product

• 1722-12-9 2-chloropyrimidine 
• 55986-39-5 lithium salt of imidazole 
• 288-32-4 1H-imidazole 
• 3934-20-1 2,6-Dichloropyrimidine 

Relevant articles and documents

Application of similarity matrices and genetic neural networks in qualitative structure-activity relationships of 2- or 4-(4- methylpiperazino)pyrimidines: 5-HT(2A) receptor antagonists

Antagonists of the 5-HT(2A) receptor are being used to treat many psychiatric disorders. The present work focuses on a group of 27 antagonists possessing varying affinities toward the receptor. These are 26 title compounds and clozapine as a reference antagonist. The active conformers of the conformationally flexible ligands were proposed by using the active rigid analogue approach and performing similarity calculations. The calculations involved genetic neural network (GNN) computations deriving QSARs from similarity matrices (SM) with cross-validated correlation coefficients exceeding 0.92. The performance of neural networks with variety of architectures was studied. As the computations were performed for cations and neutral molecules separately, the relevance of the ligand charging is discussed.

Design and biological evaluation of a novel type of potential multi-targeting antimicrobial sulfanilamide hybrids in combination of pyrimidine and azoles

This work explored a novel type of potential multi-targeting antimicrobial three-component sulfanilamide hybrids in combination of pyrimidine and azoles. The hybridized target molecules were characterized by 1H NMR, 13C NMR and HRMS spectra. Some of the developed target compounds exerted promising antimicrobial activity in comparison with the reference drugs norfloxacin and fluconazole. Noticeably, sulfanilamide hybrid 5c with pyrimidine and indole could effectively inhibit the growth of E. faecalis with MIC value of 1 μg/mL. The active molecule 5c showed low cell toxicity and did not obviously trigger the development of resistance towards the tested bacteria strains. Mechanism exploration indicated that compound 5c could not only exert efficient membrane permeability, but also intercalate into DNA of resistant E. faecalis to form 5c-DNA supramolecular complex, which might be responsible for its antimicrobial action. The further investigation showed that this molecule could be effectively transported by human serum albumins through hydrogen bonds and van der Waals force.

Synthesis and structure-activity relationship analysis of 5-HT7 receptor antagonists: Piperazin-1-yl substituted unfused heterobiaryls

A series of piperazin-1-yl substituted unfused heterobiaryls was synthesized as ligands of the 5-HT7 receptors. The goal of this project was to elucidate the structural features that affect the 5-HT7 binding affinity of this class of compounds represented by the model ligand 4-(3-furyl)-2-(4-methylpiperazin-1-yl)pyrimidine (2). The SAR studies included systematical structural changes of the pyrimidine core moiety in 2 to quinazoline, pyridine and benzene, changes of the 3-furyl group to other heteroaryl substituents, the presence of various analogs of the 4-methylpiperazin-1-yl group, as well as additional substitutions at positions 5 and 6 of the pyrimidine. Substitution of position 6 of the pyrimidine in the model ligand with an alkyl group results in a substantial increase of the binding affinity (note a change in position numbers due to the nomenclature rules). It was also demonstrated that 4-(3-furyl) moiety is crucial for the 5-HT7 binding affinity of the substituted pyrimidines, although, the pyrimidine core can be replaced with a pyridine ring without a dramatic loss of the binding affinity. The selected ethylpyrimidine (12) and butylpyrimidine (13) analogs of high 5-HT7 binding affinity showed antagonistic properties in cAMP functional test and varied selectivity profile-compound 12 can be regarded as a dual 5-HT7 /5-HT2A R ligand, and 13 as a multi-receptor (5-HT7 , 5-HT2A , 5-HT6 and D2 ) agent.