26832-08-6

Usage

Uses

Used in Pharmaceutical Synthesis:
Imidazole-4-carboxamide serves as a key component in the creation of pharmaceuticals, especially antifungal agents. Its unique structure allows it to be a versatile building block in the development of new medications.
Used in Organic Chemistry Reactions:
In the realm of organic chemistry, imidazole-4-carboxamide is utilized as a fundamental building block for the synthesis of heterocyclic compounds, which are essential in various chemical and pharmaceutical applications.
Used in Enzyme Inhibition:
Imidazole-4-carboxamide has potential therapeutic applications due to its capacity to inhibit certain enzymes, which can be crucial in managing or treating specific diseases and conditions.
Used in the Scientific and Pharmaceutical Industries:
Given its multifaceted applications, imidazole-4-carboxamide holds a significant role in both scientific research and the pharmaceutical industry, contributing to the advancement of medicine and chemical synthesis techniques.

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

Upstream product

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

Downstream Products

• 129993-48-2 1-ethylimidazole-4-carboxamide 
• 129993-49-3 1-propylimidazole-4-carboxamide 
• 294862-80-9 1-[(2S,3R)-2-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-pentyl]imidazole-4-carboxamide 
• 256461-75-3 1-[(2S,3R)-2-benzyloxy-5-(naphthalen-1-yl)-3-pentyl]imidazole-4-carboxamide 
• 256461-49-1 1-[(2S,3R)-2-benzyloxy-5-(2,3-dichlorophen-1-yl)-3-pentyl]imidazole-4-carboxamide 
• 294862-76-3 1-[(R)-4-(5-benzyloxyindol-1-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide 
• 294862-75-2 1-[(R)-4-(6-benzyloxyindol-1-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide 
• 294862-78-5 1-[(R)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide 

Relevant academic research and scientific papers

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.

Imidazole compounds

Imidazole compounds having adenosine deaminase inhibitory activity represented by formula (I) wherein R1is hydrogen, hydroxy, protected hydroxy, or aryl optionally substituted with suitable substituent(s); R2is hydrogen or lower alkyl; R3is hydroxy or protected hydroxy; R4is cyano, (hydroxy)iminoamino(lower)alkyl, carboxy, protected carboxy, heterocyclic group optionally substituted with amino, or carbamoyl optionally substituted with suitable substituent(s); and —A— is —Q— or —O—Q—, wherein Q is single bond or lower alkylene, provided that when R2is lower alkyl, then R1is hydroxy, protected hydroxy, or aryl optionally substituted with suitable substituent(s), its prodrug, or their salt. The compounds are useful for treating and/or preventing diseases for which adenosine is effective.

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.

AN EFFICIENT METHOD FOR THE PREPARATION OF 4(5)- CYANOIMIDAZOLES

We report herein a direct, cost-effective process for the preparation of 4(5)-cyanoimidazoles from the corresponding 4(5)-imidazolecarboxylates.