3315-22-8

Basic information

• Product Name: Benzoxazole, 2-(4-methoxyphenyl)-6-nitro-
• Synonyms: 2-(4-Methoxy-phenyl)-6-nitro-benzooxazole;6-Nitro-2-(4-methoxyphenyl)-benzoxazol
• CAS NO: 3315-22-8
• Molecular Formula: C14H10N2O4
• Molecular Weight: 270.244
• Mol File: 3315-22-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 175 °C (benzene)
• CAS DataBase Reference: Benzoxazole, 2-(4-methoxyphenyl)-6-nitro-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoxazole, 2-(4-methoxyphenyl)-6-nitro-(3315-22-8)
• EPA Substance Registry System: Benzoxazole, 2-(4-methoxyphenyl)-6-nitro-(3315-22-8)

Safety Data

• Hazardous Substances Data: 3315-22-8(Hazardous Substances Data)

Upstream product

• 17200-30-5 6-nitrobenzo[d]oxazole 
• 100-07-2 4-methoxy-benzoyl chloride 
• 121-88-0 5-Nitro-2-aminophenol 
• 123-11-5 4-methoxy-benzaldehyde 
• 29644-87-9 5-nitro-2-anisalamino-phenol 

Relevant articles and documents

Zr and Hf-metal-organic frameworks: Efficient and recyclable heterogeneous catalysts for the synthesis of 2-arylbenzoxazole via ring open pathway acylation reaction

Zirconium- and hafnium-based metal–organic frameworks which constructed by 12-coordinated clusters and 6-coodinated clusters were shown to be highly effective heterogeneous catalysts for the ring opening acylation of benzoxazole to 2-arylbenzoxazole under solvent free conditions. Owning the wide opening spaces structures and inherent formate sites, MOFs based on 6-connected Zr6/Hf6 node were able to identify a significantly enhanced yield in Br?nsted acid catalyzed reactions under conventional heating and microwave irradiation. In addition, the detailed mechanism of active sites of the ring opening acylation reaction was confirmed by employing of density functional theory (DFT) calculations.

Structure-activity relationships of benzimidazoles and related heterocycles as topoisomerase I poisons

A series of substituted 2-(4-methoxyphenyl)-1H-benzimidazoles were synthesized and evaluated as inhibitors of topoisomerase I. The presence of a 5-formyl-, 5-(aminocarbonyl)-, or 5-nitro group (i.e., substituents capable of acting as hydrogen bond accepters) correlated with the potential of select derivatives to inhibit topoisomerase I. In contrast to bi- and terbenzimidazoles, the substituted benzimidazoles that were active as topoisomerase I poisons exhibited minimum or no DNA binding affinity. 5-Nitro-2-(4-methoxyphenyl)-1H-benzimidazole exhibited the highest activity and was significantly more active than the 4-nitro positional isomer. The 5- and 6-nitro derivatives of 2-(4-methoxyphenyl)benzoxazole, 2-(4-methoxyphenyl)benzothiazole, and 2-(4-methoxyphenyl)indole were synthesized and their relative activity as topoisomerase I inhibitors determined. None of these heterocyclic analogues were effective in significantly inhibiting cleavable-complex formation in the presence of DNA and topoisomerase I, suggesting a high degree of structural specificity associated with the interaction of these substituted benzimidazoles with the enzyme or the enzyme-DNA complex. In evaluating their cytotoxicity, these new topoisomerase I poisons also exhibited no significant cross-resistance against cell lines that express camptothecin-resistant topoisomerase I.