142677-42-7

Basic information

• Product Name: 3-(1H-IMIDAZOL-4-YL)-PHENOL
• Synonyms: 3-(1H-IMIDAZOL-4-YL)-PHENOL
• CAS NO: 142677-42-7
• Molecular Formula: C₉H₈N₂O
• Molecular Weight: 160.17262
• Mol File: 142677-42-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(1H-IMIDAZOL-4-YL)-PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1H-IMIDAZOL-4-YL)-PHENOL(142677-42-7)
• EPA Substance Registry System: 3-(1H-IMIDAZOL-4-YL)-PHENOL(142677-42-7)

Safety Data

• Hazardous Substances Data: 142677-42-7(Hazardous Substances Data)

Upstream product

• 2491-37-4 2-bromo-1-(3-hydroxyphenyl)ethanone 
• 77287-34-4 formamide 
• 5000-65-7 2-bromo-3'-methoxyacetophenone 
• 53848-01-4 4-(3-methoxyphenyl)-1H-imidazole 

Downstream Products

• 1219829-79-4 C₁₀H₁₀N₂O 
• 1072880-86-4 3-(1-(cyclohexylcarbamoyl)-1H-imidazol-4-yl)phenyl cyclohexylcarbamate 
• 935854-24-3 tert-butyl 4-(3-hydroxy-phenyl)-imidazole-1-carboxylate 

Relevant articles and documents

UREA COMPOUNDS AND THEIR USE AS FAAH ENZYME INHIBITORS

A compound having Formula (I): wherein: R1 is selected from hydrogen, halogen, hydroxyl and C1-4 alkoxy; R2 is selected from hydrogen, halogen, hydroxyl and C1-4 alkoxy; R3 is C1-4 alkyl; R4 is aryl which is substituted with a group selected from OSO2NH2, NHCONH2, NHSO2NH2, NHSO2C1-4 alkyl and CONH2; and n is 0 or 1; or a pharmaceutically acceptable salt thereof; provided that the compound is not N-(1-benzylpiperidin-4-yl)-N-methyl-4-(4-(sulfamoylamino)phenyl)-1H-imidazole-1-carboxamide or N-(1-benzylpiperidin-4-yl)-N-methyl-4-(3-(methylsulfonamido)phenyl)-1H-imidazole-1-carboxamide. The compound may be used as an inhibitor of fatty acid amide hydrolase.

3-Heterocycle-phenyl N-alkylcarbamates as FAAH inhibitors: Design, synthesis and 3D-QSAR studies

Carbamates are a well-established class of fatty acid amide hydrolase (FAAH) inhibitors. Here we describe the synthesis of meta-substituted phenolic N-alkyl/aryl carbamates and their in vitro FAAH inhibitory activities. The most potent compound, 3-(oxazol-2yl)phenyl cyclohexylcarbamate (2a), inhibited FAAH with a sub-nanomolar IC50 value (IC50=0.74 nM). Additionally, we developed and validated three-dimensional quantitative structure-activity relationships (QSAR) models of FAAH inhibition combining the newly disclosed carbamates with our previously published inhibitors to give a total set of 99 compounds. Prior to 3D-QSAR modeling, the degree of correlation between FAAH inhibition and in silico reactivity was also established. Both 3D-QSAR methods used, CoMSIA and GRID/GOLPE, produced statistically significant models with coefficient of correlation for external prediction (R2 PRED) values of 0.732 and 0.760, respectively. These models could be of high value in further FAAH inhibitor design.

Structure based development of phenylimidazole-derived inhibitors of indoleamine 2,3-dioxygenase

Indoleamine 2,3-dioxygenase (IDO) is emerging as an important new therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. With the goal of developing more potent IDO in