208510-03-6

Basic information

• Product Name: 4-NitroiMidazole-5-carbonitrile
• Synonyms: 4-NitroiMidazole-5-carbonitrile
• CAS NO: 208510-03-6
• Molecular Formula: C4H2N4O2
• Molecular Weight: 138.08428
• Mol File: 208510-03-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-NitroiMidazole-5-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NitroiMidazole-5-carbonitrile(208510-03-6)
• EPA Substance Registry System: 4-NitroiMidazole-5-carbonitrile(208510-03-6)

Safety Data

• Hazardous Substances Data: 208510-03-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Nitroimidazole-5-carbonitrile is used as a building block for the synthesis of various pharmaceuticals. Its presence of both nitro and cyano groups makes it a versatile compound for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 4-Nitroimidazole-5-carbonitrile serves as a key intermediate in the production of agrochemicals. Its unique chemical properties allow for the creation of effective compounds for agricultural use.
Used in Anti-inflammatory Applications:
4-Nitroimidazole-5-carbonitrile is used as an anti-inflammatory agent, leveraging its chemical structure to modulate inflammatory pathways and provide relief from inflammation-related conditions.
Used in Anticancer Applications:
4-NitroiMidazole-5-carbonitrile is being investigated for its potential as an anticancer drug candidate. Its ability to target and affect cancer cells makes it a promising candidate for further research and development in oncology.
Used in Anti-tuberculosis Applications:
4-Nitroimidazole-5-carbonitrile has shown anti-tuberculosis activities, making it a valuable compound in the search for new treatments for tuberculosis, a disease that requires innovative therapeutic approaches.
Used as a Chemical Intermediate:
In the field of medicinal and synthetic chemistry, 4-Nitroimidazole-5-carbonitrile is utilized as a chemical intermediate. Its role in the synthesis of other compounds contributes to the development of a wide range of chemical products.

Upstream product

• 151-50-8 potassium cyanide 
• 19182-81-1 1,4-dinitro-1H-imidazole 
• 3034-38-6 1H-4⁽⁵⁾-nitroimidazole 

Relevant articles and documents

4(5)-Nitro-1H-imidazole-5(4)-carbonitriles. Synthesis by cine- substitution reactions

The first syntheses of 4(5)-nitro-1H-imidazole-5(4)-carbonitrile, its 2- methyl derivative and salts of both compounds with DBU have been described. The carbonitriles have been obtained by a treatment of 1,4-dinitroimidazoles with potassium cyanide in aqueous methanol solution.

Transition state structure of E. coli tRNA-specific adenosine deaminase

Bacterial tRNA-specific adenosine deaminase (TadA) catalyzes the essential deamination of adenosine to inosine at the wobble position of tRNAs and is necessary to permit a single TRNA species to recognize multiple codons. The transition state structure of Escherichia coli TadA was characterized by kinetic isotope effects (KIEs) and quantum chemical calculations. A stem loop of E. coli tRNAArg2 was used as a minimized TadA substrate, and its adenylate editing site was isotopically labeled as [1′-3H], [5′-3H2], [1′-14C], [6- 13C], [6-15N], [6-13C, 6-15N] and [1-15N]. The intrinsic KIEs of 1.014, 1.022, 0.994, 1.014 and 0.963 were obtained for [6-13C]-, [6-15N]-, [1-15N]-, [1′-3H]-, [5′-3H2]-labeled substrates, respectively. The suite of KIEs are consistent with a late S NAr transition state with a complete, pro-S-face hydroxyl attack and nearly complete N1 protonation. A significant N6-C6 dissociation at the transition state of TadA is indicated by the large [6-15N] KIE of 1.022 and corresponds to an N6-C6 distance of 2.0 A in the transition state structure. Another remarkable feature of the E. coli TadA transition state structure is the Glu70-mediated, partial proton transfer from the hydroxyl nucleophile to the N6 leaving group. KIEs correspond to H-O and H-N distances of 2.02 and 1.60 A, respectively. The large inverse [5′-3H] KIE of -3.7% and modest normal [1′-3H] KIE of 1.4% indicate that significant ribosyl 5′-reconfiguration and purine rotation occur on the path to the transition state. The late SNAr transition-state established here for E. coli TadA is similar to the late transition state reported for cytidine deaminase. It differs from the early SNAr transition states described recently for the adenosine deaminases from human, bovine, and Plasmodium falciparum sources. The ecTadA transition state structure reveals the detailed architecture for enzymatic catalysis. This approach should be readily transferable for transition state characterization of other RNA editing enzymes.