26832-08-6

Basic information

• Product Name: imidazole-4-carboxamide
• Synonyms: imidazole-4-carboxamide;1H-Imidazole-4-carboxamide;1H-IMidazol-4-carboxaMide;1H-iMidazole-5-carboxaMide;4(5)-iMidazolecarboxaMide;Imidazole-4(5)-carboxamide;imidazole-4-carboxamide (ICA)
• CAS NO: 26832-08-6
• Molecular Formula: C₄H₅N₃O
• Molecular Weight: 111.1
• Product Categories: pharmacetical;Imidazoles & Benzimidazoles
• Mol File: 26832-08-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 216 °C
• Boiling Point: 549.8 °C at 760 mmHg
• Flash Point: 286.3 °C
• Appearance: /
• Density: 1.394 g/cm³
• Vapor Pressure: 3.89E-12mmHg at 25°C
• Refractive Index: 1.612
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 11.75±0.10(Predicted)
• CAS DataBase Reference: imidazole-4-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: imidazole-4-carboxamide(26832-08-6)
• EPA Substance Registry System: imidazole-4-carboxamide(26832-08-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 26832-08-6(Hazardous Substances Data)

Usage

General Description

Imidazole-4-carboxamide is an organic compound with the chemical formula C4H4N3O. It is a derivative of imidazole, containing a carboxamide functional group at the 4-position. Imidazole-4-carboxamide is used in the synthesis of pharmaceuticals, particularly antifungal agents. It is also used as a building block in organic chemistry reactions, such as in the formation of heterocyclic compounds. Imidazole-4-carboxamide has potential therapeutic applications due to its ability to inhibit certain enzymes and biological processes. Overall, imidazole-4-carboxamide plays a significant role in medicinal and synthetic chemistry, making it an important compound in the scientific and pharmaceutical industries.

InChI:InChI=1/C4H5N3O/c5-4(8)3-1-6-2-7-3/h1-2H,(H2,5,8)(H,6,7)

Upstream product

• 570-22-9 4,5-imidazoledicarboxylic acid 
• 23785-21-9 1H-imidazole-5-carboxylic acid ethyl ester 
• 7008-85-7 5-diazoimidazole-4-carboxamide 
• 17325-26-7 Methyl imidazole-4-carboxylate 
• 57-48-7 D-Fructose 
• 807306-71-4 3,7-bis(dimethylamine)phenothiazonium 
• 57-48-7 fructose 

Downstream Products

• 583873-31-8 1-{(3R,4S)-4-(tert-butyldimethylsilyloxy)-1-[2-(4-chlorophenyl)-4-benzoxazolyl]-3-pentyl}imidazole-4-carboxamide 
• 583873-38-5 1-{(3R,4S)-4-(tert-butyldimethylsilyloxy)-1-[2-(4-chlorophenyl)-7-benzoxazolyl]-3-pentyl}imidazole-4-carboxamide 
• 256461-49-1 1-[(2S,3R)-2-benzyloxy-5-(2,3-dichlorophen-1-yl)-3-pentyl]imidazole-4-carboxamide 
• 57090-88-7 1H-imidazole-4-carbonitrile 

Relevant articles and documents

Biosynthesis of the Fairy Chemicals, 2-Azahypoxanthine and Imidazole-4-carboxamide, in the Fairy Ring-Forming Fungus Lepista sordida

Fairy rings resulting from a fungus-plant interaction appear worldwide. 2-Azahypoxanthine (AHX) and imidazole-4-carboxamide (ICA) were first isolated from the culture broth of one of the fairy ring-forming fungi, Lepista sordida. Afterward, a common metabolite of AHX in plants, 2-aza-8-oxohypoxanthine (AOH), was found in AHX-treated rice. The biosynthetic pathway of the three compounds that are named as fairy chemicals (FCs) in plants has been partially elucidated; however, that in mushrooms remains unknown. In this study, it was revealed that the carbon skeletons of AHX and ICA were constructed from Gly in L. sordida mycelia and the fungus metabolized 5-aminoimidazole-4-carboxamide (AICA) to both of the compounds. These results indicated that FCs were biosynthesized by a diversion of the purine metabolic pathway in L. sordida mycelia, similar to that in plants. Furthermore, we showed that recombinant adenine phosphoribosyltransferase (APRT) catalyzed reversible interconversion not only between 5-aminoimidazole-4-carboxamide-1-β-d-ribofuranosyl 5′-monophosphate (AICAR) and AICA but also between ICA-ribotide (ICAR) and ICA. Furthermore, the presence of ICAR in L. sordida mycelia was proven for the first time by LC-MS/MS detection, and this study provided the first report that there was a novel metabolic pathway of ICA in which its ribotide was an intermediate in the fungus.

Derivatives of imidazole-4-carboxamide as substrates for various DNA polymerases

A series of nucleotide analogs bearing imidazole 4-carboxamides as bases were synthetized. The ability of Klenow fragment of pol I and HIV-1 reverse transcriptase to use these 5'-triphosphate derivatives as substrates in DNA elongation reactions was investigated.