14953-62-9

Basic information

• Product Name: 4-nitro-5-phenyl-1H-imidazole
• Synonyms: 4-nitro-5-phenyl-1H-imidazole;5-NITRO-4-PHENYL-1H-IMIDAZOLE
• CAS NO: 14953-62-9
• Molecular Formula: C₉H₇N₃O₂
• Molecular Weight: 189.17
• Mol File: 14953-62-9.mol

Chemical Properties

• Boiling Point: 449.2°Cat760mmHg
• Flash Point: 225.5°C
• Appearance: /
• Density: 1.369g/cm³
• Vapor Pressure: 7.73E-08mmHg at 25°C
• Refractive Index: 1.642
• CAS DataBase Reference: 4-nitro-5-phenyl-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-nitro-5-phenyl-1H-imidazole(14953-62-9)
• EPA Substance Registry System: 4-nitro-5-phenyl-1H-imidazole(14953-62-9)

Safety Data

• Hazardous Substances Data: 14953-62-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H7N3O2/c13-12(14)9-8(10-6-11-9)7-4-2-1-3-5-7/h1-6H,(H,10,11)

Upstream product

• 6963-65-1 4-bromo-5-nitro-1H-imidazole 
• 98-80-6 phenylboronic acid 
• 72798-75-5 4⁽⁵⁾-(p-aminophenyl)-5⁽⁴⁾-nitroimidazole 

Downstream Products

• 111328-06-4 5-Phenyl-3H-imidazol-4-ylamine 
• 1039984-25-2 1-methyl-4-phenyl-5-aminoimidazole 
• 14953-63-0 1-methyl-4-phenyl-5-nitroimidazole 
• 111380-10-0 1-methyl-4-nitro-5-phenyl-1H-imidazole 

Relevant articles and documents

IMIDAZOTETRAZINE COMPOUNDS

New synthetic methods to provide access to previously unexplored functionality at the C8 position of imidazotetrazines. Through synthesis and evaluation of a suite of compounds with a range of aqueous stabilities (from 0.5 to 40 hours), a predictive model for imidazotetrazine hydrolytic stability based on the Hammett constant of the C8 substituent was derived. Promising compounds were identified that possess activity against a panel of GBM cell lines, appropriate hydrolytic and metabolic stability, and brain-to-serum ratios dramatically elevated relative to TMZ, leading to lower hematological toxicity profiles and superior activity to TMZ in a mouse model of GBM.

Tunable Stability of Imidazotetrazines Leads to a Potent Compound for Glioblastoma

Even in the era of personalized medicine and immunotherapy, temozolomide (TMZ), a small molecule DNA alkylating agent, remains the standard-of-care for glioblastoma (GBM). TMZ has an unusual mode-of-action, spontaneously converting to its active component via hydrolysis in vivo. While TMZ has been FDA approved for two decades, it provides little benefit to patients whose tumors express the resistance enzyme MGMT and gives rise to systemic toxicity through myelosuppression. TMZ was first synthesized in 1984, but certain key derivatives have been inaccessible due to the chemical sensitivity of TMZ, precluding broad exploration of the link between imidazotetrazine structure and biological activity. Here, we sought to discern the relationship between the hydrolytic stability and anticancer activity of imidazotetrazines, with the objectives of identifying optimal timing for prodrug activation and developing suitable compounds with enhanced efficacy via increased blood-brain barrier penetrance. This work necessitated the development of new synthetic methods to provide access to previously unexplored functionality (such as aliphatic, ketone, halogen, and aryl groups) at the C8 position of imidazotetrazines. Through synthesis and evaluation of a suite of compounds with a range of aqueous stabilities (from 0.5 to 40 h), we derive a predictive model for imidazotetrazine hydrolytic stability based on the Hammett constant of the C8 substituent. Promising compounds were identified that possess activity against a panel of GBM cell lines, appropriate hydrolytic and metabolic stability, and brain-to-serum ratios dramatically elevated relative to TMZ, leading to lower hematological toxicity profiles and superior activity to TMZ in a mouse model of GBM. This work points a clear path forward for the development of novel and effective anticancer imidazotetrazines.

Nitrosoimidazoles: Highly Bactericidal Analogues of 5-Nitroimidazole Drugs

It is believed that metronidazole and related 5-nitroimidazoles are activated by reduction of the nitro group and that the active species has a nitrogen functionality of intermediate oxidation state.However, the preparation and isolation of the active for