161887-05-4

Basic information

• Product Name: 3-(1H-IMIDAZOL-2-YL)-PHENYLAMINE
• Synonyms: AKOS BB-8922;3-(1H-IMIDAZOL-2-YL)-PHENYLAMINE;3-(2-Imidazolyl)aniline
• CAS NO: 161887-05-4
• Molecular Formula: C₉H₉N₃
• Molecular Weight: 159.18786
• Mol File: 161887-05-4.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(1H-IMIDAZOL-2-YL)-PHENYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1H-IMIDAZOL-2-YL)-PHENYLAMINE(161887-05-4)
• EPA Substance Registry System: 3-(1H-IMIDAZOL-2-YL)-PHENYLAMINE(161887-05-4)

Safety Data

• Hazardous Substances Data: 161887-05-4(Hazardous Substances Data)

Usage

General Description

3-(1H-IMIDAZOL-2-YL)-PHENYLAMINE is a chemical compound with the molecular formula C9H10N2. It is a phenylamine derivative that contains an imidazole ring, which is a five-membered heterocyclic ring containing three carbon atoms and two nitrogen atoms. 3-(1H-IMIDAZOL-2-YL)-PHENYLAMINE is commonly used in pharmaceutical research and drug development due to its potential biological activity and ability to interact with biological targets. It is also used as a building block in the synthesis of various organic molecules. The imidazole moiety in 3-(1H-IMIDAZOL-2-YL)-PHENYLAMINE makes it an important component in a wide range of pharmaceuticals, including antifungal drugs, histamine receptor antagonists, and anti-inflammatory agents.

Upstream product

• 54316-43-7 3-nitro-benzimidic acid methyl ester 
• 619-24-9 3-nitrobenzonitrile 
• 13682-18-3 2‐(3‐nitrophenyl)‐1H‐imidazole 

Downstream Products

• 842127-50-8 compound 43 

Relevant articles and documents

Diarylureas Containing 5-Membered Heterocycles as CB1 Receptor Allosteric Modulators: Design, Synthesis, and Pharmacological Evaluation

Allosteric modulators have attracted significant interest as an alternate strategy to modulate CB1 receptor signaling for therapeutic benefits that may avoid the adverse effects associated with orthosteric ligands. Here we extended our previous structure-activity relationship studies on the diarylurea-based CB1 negative allosteric modulators (NAMs) by introducing five-membered heterocycles to replace the 5-pyrrolidinylpyridinyl group in PSNCBAM-1 (1), one of the first generation CB1 allosteric modulators. Many of these compounds had comparable potency to 1 in blocking the CB1 agonist CP55,940 stimulated calcium mobilization and [35S]GTP-γ-S binding. Similar to 1, most compounds showed positive cooperativity by increasing [3H]CP55,940 binding, consistent with the positive allosteric modulator (PAM)-antagonist mechanism. Interestingly, these compounds exhibited differences in ability to increase specific binding of [3H]CP55,940 and decrease binding of the antagonist [3H]SR141716. In saturation binding studies, only increases in [3H]CP55,940 Bmax, but not Kd, were observed, suggesting that these compounds stabilize low affinity receptors into a high affinity state. Among the series, the 2-pyrrolyl analogue (13) exhibited greater potency than 1 in the [35S]GTP-γ-S binding assay and significantly enhanced the maximum binding level in the [3H]CP5,5940 binding assay, indicating greater CB1 receptor affinity and/or cooperativity.

Design and synthesis of 2-arylbenzimidazoles and evaluation of their inhibitory effect against Chlamydia pneumoniae

Chlamydia pneumoniae is an intracellular bacterium that responds poorly to antibiotic treatment. Insufficient antibiotic usage leads to chronic infection, which is linked to disease processes of asthma, atherosclerosis, and Alzheimer's disease. The Chlamydia research lacks genetic tools exploited by other antimicrobial research, and thus other approaches to drug discovery must be applied. A set of 2-arylbenzimidazoles was designed based on our earlier findings, and 33 derivatives were synthesized. Derivatives were assayed against C. pneumoniae strain CWL-029 in an acute infection model using TR-FIA method at a concentration of 10 μM, and the effects of the derivatives on the host cell viability were evaluated at the same concentration. Fourteen compounds showed at least 80% inhibition, with only minor changes in host cell viability. Nine most potential compounds were evaluated using immunofluorescence microscopy on two different strains of C. pneumoniae CWL-029 and CV-6. The N-[3-(1H-benzimidazol-2-yl)phenyl]-3-methylbenzamide (42) had minimal inhibitory concentration (MIC) of 10 μM against CWL-029 and 6.3 μM against the clinical strain CV-6. This study shows the high antichlamydial potential of 2-arylbenzimidazoles, which also seem to have good characteristics for lead compounds.

Method for treating neoplasia with amino or pyridylamino cyclobutene derivatives

A method for inhibiting neoplasia, particularly cancerous and precancerous lesions by exposing the affected cells to amino or pyridylamino cyclobutane derivatives.