67333-75-9

Basic information

• Product Name: 1H-Imidazole, 1-(3,5-dimethoxybenzoyl)-
• CAS NO: 67333-75-9
• Molecular Formula: C12H12N2O3
• Molecular Weight: 232.239
• Mol File: 67333-75-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1H-Imidazole, 1-(3,5-dimethoxybenzoyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazole, 1-(3,5-dimethoxybenzoyl)-(67333-75-9)
• EPA Substance Registry System: 1H-Imidazole, 1-(3,5-dimethoxybenzoyl)-(67333-75-9)

Safety Data

• Hazardous Substances Data: 67333-75-9(Hazardous Substances Data)

Upstream product

• 1132-21-4 3,5-dimethoxybenzoic acid 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 1420471-39-1 allyl (3,5-dimethoxyphenyl)carbamate 
• 710311-79-8 N-hydroxy-3,5-dimethoxybenzamide 
• 54132-76-2 3,5-dimethoxyphenyl isocyanate 
• 97025-16-6 3-(3,5-dimethoxyphenyl)-3-oxopropionic acid ethyl ester 
• 67333-71-5 1-(3,5-Dimethoxy-phenyl)-2-nitro-ethanone 

Relevant articles and documents

Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine-or H2O2-induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.

N-methylimidazole-catalyzed synthesis of carbamates from hydroxamic acids via the lossen rearrangement

An efficient, one-pot, N-methylimidazole (NMI) accelerated synthesis of aromatic and aliphatic carbamates via the Lossen rearrangement is reported. NMI is a catalyst for the conversion of isocyanate intermediates to the carbamates. Moreover, the utility of arylsulfonyl chloride in combination with NMI minimizes the formation of often-observed hydroxamate-isocyanate dimers during the sequence. Under the present conditions, lowering of temperatures is also possible, enabling a mild protocol.