23274-21-7

Basic information

• Product Name: 5-Amino-1-(2-O,3-O,5-O-triacetyl-β-D-ribofuranosyl)-1H-imidazole-4-carboxamide
• Synonyms: 5-Amino-1-(2-O,3-O,5-O-triacetyl-β-D-ribofuranosyl)-1H-imidazole-4-carboxamide;5-AMino-1-β-D-ribofuranosyl-iMidazole-4-carboxaMide 2',3',5'-Triacetate;NSC 157736
• CAS NO: 23274-21-7
• Molecular Formula: C₁₅H₂₀N₄O₈
• Molecular Weight: 384.3413
• Product Categories: Bases & Related Reagents;Inhibitors;Nucleotides;Nucleotides, Bases & Related Reagents, Inhibitors
• Mol File: 23274-21-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 69 °C
• Boiling Point: 618.4°Cat760mmHg
• Flash Point: 327.8°C
• Appearance: /
• Density: 1.61g/cm³
• Vapor Pressure: 3.19E-15mmHg at 25°C
• Refractive Index: 1.638
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 15.28±0.50(Predicted)
• CAS DataBase Reference: 5-Amino-1-(2-O,3-O,5-O-triacetyl-β-D-ribofuranosyl)-1H-imidazole-4-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-1-(2-O,3-O,5-O-triacetyl-β-D-ribofuranosyl)-1H-imidazole-4-carboxamide(23274-21-7)
• EPA Substance Registry System: 5-Amino-1-(2-O,3-O,5-O-triacetyl-β-D-ribofuranosyl)-1H-imidazole-4-carboxamide(23274-21-7)

Safety Data

• Hazardous Substances Data: 23274-21-7(Hazardous Substances Data)

Usage

Chemical Properties

Brown Semi Solid

InChI:InChI=1/C15H20N4O8/c1-6(20)24-4-9-11(25-7(2)21)12(26-8(3)22)15(27-9)19-5-18-10(13(19)16)14(17)23/h5,9,11-12,15H,4,16H2,1-3H3,(H2,17,23)

Upstream product

• 2627-69-2 AICA riboside 
• 108-24-7 acetic anhydride 

Downstream Products

• 59354-00-6 5-iodo-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 
• 126004-19-1 5-(3-hydroxy-1-propyn-1-yl)-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carbonitrile 
• 131195-08-9 5-(4-phenyl-1-butyn-1-yl)-1-β-D-ribofuranosylimidazole-4-carboxamide 
• 126004-22-6 5-(phenylethyn-1-yl)-1-β-D-ribofuranosylimidazole-4-carbonitrile 
• 131195-04-5 5-(cyclohexylethyn-1-yl)-1-β-D-ribofuranosylimidazole-4-carboxamide 
• 126004-14-6 5-(3-hydroxy-1-propyn-1-yl)-1-β-D-ribofuranosylimidazole-4-carbonitrile 
• 126004-13-5 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carbonitrile 
• 532-20-7 beta-D-xylofuranoside 
• 50924-49-7 Mizoribine^<*> 
• 118908-03-5 5-(phenylethyn-1-yl)-1-β-D-ribofuranosylimidazole-4-carboxamide 
• 118908-07-9 5-ethynyl-1-(β-D-ribofuranosyl)imidazole-4-carboxamide 
• 23192-64-5 5-amino-1-β-D-ribofuranosyl-1H-imidazole-4-carbonitrile 
• 79957-16-7 2-formyladenosine 

Relevant articles and documents

New synthetic AICAR derivatives with enhanced AMPK and ACC activation

5-Aminoimidazole-4-carboxamide riboside (AICAR) has an important role in the regulation of the cellular metabolism showing a broad spectrum of therapeutic activities against different metabolic processes. Due to these proven AICAR properties, we have desi

METHODS, COMPOSITIONS, AND FORMULATIONS FOR PREVENTING OR REDUCING ADVERSE EFFECTS IN A PATIENT

The present invention provides methods, compositions, formulations, and kits related to acadesine, or a prodrug, analog, or salt thereof, and/or a blood clotting inhibitor for preventing or reducing adverse side effects in a patient. The type of patient that may benefit includes a patient with decreased left ventricular function, a patient with a prior myocardial infarction, a patient undergoing non-vascular surgery, or a fetus during labor and delivery.

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.