89532-38-7

Usage

Uses

Used in Organic Synthesis:
2-Cyclopropyl-1H-imidazole serves as a key building block in organic synthesis, utilized for the creation of various complex organic molecules. Its cyclopropyl group and imidazole ring provide unique structural features that facilitate the synthesis of a wide range of compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-Cyclopropyl-1H-imidazole is employed as a precursor to the development of pharmaceuticals. Its incorporation into drug molecules contributes to the creation of antifungal and antimicrobial agents, highlighting its importance in combating infections and diseases.
Used in Drug Discovery and Development:
The biological activity of 2-Cyclopropyl-1H-imidazole makes it a valuable tool in drug discovery and development. Its unique properties allow for the exploration of new therapeutic agents and the enhancement of existing ones, potentially leading to more effective treatments for various medical conditions.
Used in Scientific Research:
2-Cyclopropyl-1H-imidazole's versatility and reactivity contribute to its use in scientific research across multiple disciplines. Researchers leverage its properties to investigate new chemical reactions, explore the synthesis of novel compounds, and study biological interactions, thereby advancing knowledge in chemistry and related fields.
Used in Industrial Processes:
2-Cyclopropyl-1H-imidazole's potential applications extend to various industrial processes, where its unique structure and reactivity can be harnessed for the production of specialty chemicals, pharmaceutical intermediates, and other high-value products. This contributes to the innovation and efficiency of industrial operations in the chemical and pharmaceutical sectors.

Upstream product

• 109152-85-4 2-Cyclopropyl-4,5-dihydro-1H-imidazol 
• 131543-46-9 Glyoxal 
• 1489-69-6 Cyclopropanecarboxaldehyde 
• 5500-21-0 cyclopropropanecarbonitrile 
• 22483-09-6 2,2-dimethoxyethylamine 

Downstream Products

• 1202690-97-8 3-cyclopropyl-1-iodo-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine 
• 1202690-99-0 3-cyclopropyl-1-iodo-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester 
• 1208318-52-8 ethyl 3-(1-(4-carbamoyl-2-methylphenyl)-5-(4-(2-cyclopropyl-1H-imidazol-1-yl)phenyl)-1H-pyrrol-2-yl)propanoate 
• 445302-05-6 1H-Imidazole, 2-cyclopropyl-1-[[1-(3,4-dichlorophenyl)-1H-imidazol-4-yl]methyl]- 

Relevant academic research and scientific papers

Imidazole-based pinanamine derivatives: Discovery of dual inhibitors of the wild-type and drug-resistant mutant of the influenza A virus

We previously reported potent hit compound 4 inhibiting the wild-type influenza A virus A/HK/68 (H3N2) and A/M2-S31N mutant viruses A/WS/33 (H1N1), with its latter activity quite weak. To further increase its potency, a structure-activity relationship study of a series of imidazole-linked pinanamine derivatives was conducted by modifying the imidazole ring of this compound. Several compounds of this series inhibited the amantadine-sensitive virus at low micromolar concentrations. Among them, 33 was the most potent compound, which was identified as being active on an amantadine-sensitive virus through blocking of the viral M2 ion channel. Furthermore, 33 markedly inhibited the amantadine-resistant virus (IC50 = 3.4 μM) and its activity increased by almost 24-fold compared to initial compound, with its action mechanism being not M2 channel mediated.

HETEROCYCLIC MODULATORS OF LIPID SYNTHESIS AND COMBINATIONS THEREOF

Heterocyclic modulators of lipid synthesis are provided as well as pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising such compounds; and methods of treating conditions characterized by disregulation of a fatty acid synthase pathway by the administration of such compounds and combinations of such compounds and other therapeutic agents.

Pyrrole inhibitors of S-nitrosoglutathione reductase as therapeutic agents

The present invention is directed to inhibitors of S-nitrosoglutathione reductase (GSNOR), pharmaceutical compositions comprising such GSNOR inhibitors, and methods of making and using the same.

HETEROCYCLIC MODULATORS OF LIPID SYNTHESIS

Heterocyclic modulators of lipid synthesis are provided as well as pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising such compounds; and methods of treating conditions characterized by disregulation of a fatty acid synthase pathway by the administration of such compounds.

Synthesis, structure-activity relationship studies, and identification of novel 5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine derivatives as dual orexin receptor antagonists. Part 1

A novel series of non-peptidic OX1R/OX2R orexin receptor antagonists was prepared by heterocyclic replacement of the dimethoxyphenyl moiety contained in the tetrahydroisoquinoline core skeleton of almorexant. Introduction of substituted imidazole moieties delivered potent dual orexin receptor antagonists with nanomolar potency for hOX1R and hOX2R suitable for further fine-tuning. The preparation of these novel orexin receptor antagonists and the outcome of preliminary structure-activity relationship studies are described in this communication.

Structure-activity relationship studies and sleep-promoting activity of novel 1-chloro-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine derivatives as dual orexin receptor antagonists. Part 2

Replacement of the dimethoxyphenyl moiety in the core skeleton of almorexant by appropriately substituted imidazoles afforded novel 1-chloro-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine derivatives as potent dual orexin receptor antagonists. We describe in th

Compounds and Compositions as Protein Kinase Inhibitors

The present invention provides compounds of Formula I or II: wherein R1, R1b, R2, R3, R4, R5, R6 and R7 are defined herein. The compounds of Formula (I) or (II) and pharmaceutical compositions thereof are useful for the treatment of B-Raf-associated diseases.

Discovery of potent and novel S-nitrosoglutathione reductase inhibitors devoid of cytochrome P450 activities

The pyrrole based N6022 was recently identified as a potent, selective, reversible, and efficacious S-nitrosoglutathione reductase (GSNOR) inhibitor and is currently undergoing clinical development for the treatment of acute asthma. GSNOR is a member of the alcohol dehydrogenase family (ADH) and regulates the levels of S-nitrosothiols (SNOs) through catabolism of S-nitrosoglutathione (GSNO). Reduced levels of GSNO, as well as other nitrosothiols (SNOs), have been implicated in the pathogenesis of many diseases including those of the respiratory, cardiovascular, and gastrointestinal systems. Preservation of endogenous SNOs through GSNOR inhibition presents a novel therapeutic approach with broad applicability. We describe here the synthesis and structure-activity relationships (SAR) of novel pyrrole based analogues of N6022 focusing on removal of cytochrome P450 inhibition activities. We identified potent and novel GSNOR inhibitors having reduced CYP inhibition activities and demonstrated efficacy in a mouse ovalbumin (OVA) model of asthma.

5,6,7,8-TETRAHYDRO-IMIDAZO[1,5-A]PYRAZINE COMPOUNDS

The invention relates to 5,6,7,8-tetrahydro-imidazo[1,5- a]pyrazine derivatives of formula (I) wherein R1, R2, R3, and R4 are as described n the description, to salts, especially pharmaceutically acceptable salts thereof, and to the use of such compounds as medicaments; especially as orexin receptor antagonists.

Imidazole derivatives

Novel imidazole derivatives are disclosed. These compounds have a good affinity to the NMDA (N-methyl-D-aspartate)-receptor subtype selective blockers, which have a key function in modulating neuronal activity and plasticity which makes them key players in mediating processes underlying development of CNS as well as learning and memory formation. These compounds are useful in the control or treatment of diseases mediated by this receptor.