N-Phenyl-1H-imidazol-2-amine
Names and Identifiers of N-Phenyl-1H-imidazol-2-amine
CAS Number |
54707-87-8 |
|---|---|
IUPAC Name |
N-phenyl-1H-imidazol-2-amine |
InChI |
InChI=1S/C9H9N3/c1-2-4-8(5-3-1)12-9-10-6-7-11-9/h1-7H,(H2,10,11,12) |
InChIKey |
YCAXQAUEKMQYQH-UHFFFAOYSA-N |
Canonical SMILES |
C1=CC=C(C=C1)NC2=NC=CN2 |
Physical and chemical properties of N-Phenyl-1H-imidazol-2-amine
Exact Mass |
159.08000 |
|---|---|
LogP |
2.22630 |
Molecular Formula |
C9H9N3 |
Molecular Weight |
159.18800 |
PSA |
40.71000 |
Storage condition |
2-8°C |
Safety Information of N-Phenyl-1H-imidazol-2-amine
Applications of N-Phenyl-1H-imidazol-2-amine
N-Phenyl-1H-imidazol-2-amine has several applications:
- Pharmaceuticals: It is primarily researched for its anti-inflammatory and anticancer properties.
- Catalysis: Imidazole derivatives are often used as catalysts in organic synthesis due to their ability to stabilize transition states.
- Biological Probes: The compound serves as a scaffold for developing new biologically active molecules targeting specific enzymes and receptors.
Interaction Studies of N-Phenyl-1H-imidazol-2-amine
Studies have shown that N-phenyl substitution enhances interaction with biological targets, improving binding affinities and selectivity. For instance, modifications at the phenyl group can significantly influence the pharmacokinetic properties and efficacy of the compound as an inhibitor against vascular adhesion protein. Computational docking studies further elucidate these interactions at a molecular level, providing insights into structure–activity relationships.
Similar CompoundsSeveral compounds share structural similarities with N-phenyl-1H-imidazol-2-amine. Here are some notable examples:
| Compound Name | Similarity Index |
|---|---|
| 5-(3-Bromophenyl)-1H-imidazole | 0.73 |
| 4-Phenyl-1H-imidazol-2-amines hemisulfate | 0.71 |
| 5-Phenyl-1H-imidazole-2-carbaldehyde | 0.71 |
| N-Methyl-4-(1-imidazolyl)benzylamine | 0.70 |
| (4-(1H-Imidazol-1-yl)phenyl)methanamine hydrochloride | 0.67 |
Biological Activity of N-Phenyl-1H-imidazol-2-amine
N-Phenyl-1H-imidazol-2-amine has shown significant biological activity, particularly in medicinal chemistry. It has been identified as a potent inhibitor of vascular adhesion protein-1, which plays a crucial role in inflammatory processes and diabetic macular edema treatment. Additionally, its derivatives have been explored for their potential as inhibitors against other targets, including indoleamine 2,3-dioxygenase, which is involved in immune regulation.