23192-63-4

Basic information

• Product Name: 5-Amino-1-(2’,3’,5’-tri-O-acetyl--D-ribofuranosyl)-imidazole-4-carbonitrile
• Synonyms: 5-Amino-1-(2’,3’,5’-tri-O-acetyl--D-ribofuranosyl)-imidazole-4-carbonitrile;5-AMino-1-β-D-ribofuranosyl-iMidazole-4-carbonitrile 2',3',5'-Triacetate
• CAS NO: 23192-63-4
• Molecular Formula: C₁₅H₁₈N₄O₇
• Molecular Weight: 366.32602
• Product Categories: Bases & Related Reagents;Inhibitors;Nucleotides;Nucleotides, Bases & Related Reagents, Inhibitors
• Mol File: 23192-63-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 601.911°C at 760 mmHg
• Flash Point: 317.825°C
• Appearance: /
• Density: 1.518g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.622
• Solubility: Chloroform, Ethanol
• PKA: 1.28±0.61(Predicted)
• CAS DataBase Reference: 5-Amino-1-(2’,3’,5’-tri-O-acetyl--D-ribofuranosyl)-imidazole-4-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-1-(2’,3’,5’-tri-O-acetyl--D-ribofuranosyl)-imidazole-4-carbonitrile(23192-63-4)
• EPA Substance Registry System: 5-Amino-1-(2’,3’,5’-tri-O-acetyl--D-ribofuranosyl)-imidazole-4-carbonitrile(23192-63-4)

Safety Data

• Hazardous Substances Data: 23192-63-4(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Foam/Solid

Uses

Protected imidazole derivative

InChI:InChI=1/C15H18N4O7/c1-7(20)23-5-11-12(24-8(2)21)13(25-9(3)22)15(26-11)19-6-18-10(4-16)14(19)17/h6,11-13,15H,5,17H2,1-3H3/t11-,12+,13+,15-/m1/s1

Upstream product

• 23274-21-7 5-Amino-4-carbamoyl-1β-(2',3',5'-tri-O-acetyl-D-ribofuranosyl)imidazole 
• 2627-69-2 AICA riboside 

Downstream Products

• 59354-00-6 5-iodo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carbonitrile 
• 23192-64-5 5-amino-1-β-D-ribofuranosyl-1H-imidazole-4-carbonitrile 
• 79957-16-7 2-formyladenosine 
• 532-20-7 beta-D-xylofuranoside 
• 126004-13-5 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carbonitrile 
• 118908-07-9 5-ethynyl-1-(β-D-ribofuranosyl)imidazole-4-carboxamide 
• 126004-14-6 5-(3-hydroxy-1-propyn-1-yl)-1-β-D-ribofuranosylimidazole-4-carbonitrile 
• 126004-22-6 5-(phenylethyn-1-yl)-1-β-D-ribofuranosylimidazole-4-carbonitrile 
• 126004-19-1 5-(3-hydroxy-1-propyn-1-yl)-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carbonitrile 
• 126004-18-0 5-(phenylethyn-1-yl)-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carbonitrile 
• 126004-21-5 5-<(trimethylsilyl)-1-ethyn-1-yl>-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carbonitrile 

Relevant articles and documents

ISOLATION AND SYNTHESYS OF 1-METHYLISOGUANOSINE, A POTENT PHARMACOLOGICALLY ACTIVE CONSTITUENT FROM THE MARINE SPONGE TEDANIA DIGITATA

A new pharmacologically active agent isolated from the marine sponge Tedania digitata has been identified as 1-methylisoguanosine(1) by spectral and degradative chemical methods and synthesis from a β-D-ribofuranosylimidazole (2).

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.

1-Methylisoguanosine, a pharmacologically active agent from a marine sponge

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