126004-13-5

Basic information

• Product Name: 5-Ethynyl-1-(-D-ribofuranosyl)-imidazo-4-carbonitrile
• Synonyms: 5-Ethynyl-1-(-D-ribofuranosyl)-imidazo-4-carbonitrile
• CAS NO: 126004-13-5
• Molecular Formula: C₁₁H₁₁N₃O₄
• Molecular Weight: 249.22274
• Product Categories: Bases & Related Reagents;Inhibitors;Nucleotides;Nucleotides, Bases & Related Reagents, Inhibitors
• Mol File: 126004-13-5.mol

Chemical Properties

• Boiling Point: 662.7±55.0 °C(Predicted)
• Appearance: /
• Density: 1.53±0.1 g/cm3(Predicted)
• Solubility: Methanol
• PKA: 13.17±0.70(Predicted)
• CAS DataBase Reference: 5-Ethynyl-1-(-D-ribofuranosyl)-imidazo-4-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Ethynyl-1-(-D-ribofuranosyl)-imidazo-4-carbonitrile(126004-13-5)
• EPA Substance Registry System: 5-Ethynyl-1-(-D-ribofuranosyl)-imidazo-4-carbonitrile(126004-13-5)

Safety Data

• Hazardous Substances Data: 126004-13-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-Ethynyl-1-(β-D-ribofuranosyl)-imidazo-4-carbonitrile is used as a synthetic intermediate for the creation of other organic compounds. Its unique structure, featuring an ethynyl group and a D-ribofuranosyl moiety, allows it to be a versatile building block in the synthesis of complex organic molecules, potentially for use in pharmaceuticals, materials science, or other specialized applications.
Given the limited information provided, the specific applications in different industries are not detailed. However, the compound's role as a synthetic intermediate suggests that it could be utilized across various chemical and pharmaceutical industries for the development of new products. Further research and development would be necessary to explore and confirm its specific uses in these contexts.

Upstream product

• 23274-21-7 5-Amino-4-carbamoyl-1β-(2',3',5'-tri-O-acetyl-D-ribofuranosyl)imidazole 
• 23192-63-4 5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carbonitrile 
• 59354-00-6 5-iodo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carbonitrile 
• 2627-69-2 AICA riboside 
• 126004-21-5 5-<(trimethylsilyl)-1-ethyn-1-yl>-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carbonitrile 

Downstream Products

• 118908-07-9 5-ethynyl-1-(β-D-ribofuranosyl)imidazole-4-carboxamide 
• 147212-86-0 4-amino-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazo<4,5-c>pyridine 
• 147212-83-7 5-ethynyl-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazole-4-carbonitrile 

Relevant articles and documents

Nucleosides and nucleotides. 96. Synthesis and antitumor activity of 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide (EICAR) and its derivatives

The palladium-catalyzed cross-coupling reaction of 5-iodo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl) imidazole-4-carboxamide (8) with various terminal alkynes in the presence of bis(benzonitrile)palladium dichloride in acetonitrile containing triethylamine gave the desired 5-alkynyl derivatives 9 in high yields. However, when (trimethylsilyl)acetylene was used, the only isolable product was the undesired dimer, 1,2-bis(4-carbamoyl-1-β-D-ribofuranosylimidazol-5-yl)acetylene derivative 10a. To circumvent such dimer formation, the reaction was done with use of trimethyl[(tributylstannyl)ethynyl]silane in the absence of triethylamine to afford the desired 5-(2-trimethylsilyl)ethynyl derivative 9a in good yield. Furthermore, the similar cross-coupling reaction of 5-iodo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl) imidazole-4-carbonitrile (12) with (trimethylsilyl)acetylene also afforded the desired nucleoside 13a. Deprotection of these compounds furnished 5-alkynyl-1-β-D-ribofuranosylimidazole-4-carboxamides (6b-k) and -carbonitriles (14b-f). Among these, 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide (6b, EICAR) is the most potent inhibitor of growth of the various tumor cells in culture including human solid tumor cells. Preliminary results of in vivo antitumor activity against murine leukemias L1210 and P388 are also described.