23274-21-7

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

• 23192-63-4 5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carbonitrile 
• 79957-16-7 2-formyladenosine 
• 23192-64-5 5-amino-1-β-D-ribofuranosyl-1H-imidazole-4-carbonitrile 
• 50924-49-7 Mizoribine^<*> 
• 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 
• 118908-03-5 5-(phenylethyn-1-yl)-1-β-D-ribofuranosylimidazole-4-carboxamide 

Relevant academic research and scientific papers

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 transdermal administration of AICA riboside, or a prodrugs, analogs, or salts thereof, and/or a blood clotting inhibitor for preventing or reducing adverse side effects in a patient. The type of patient that may benefit incl

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.

AICA riboside analogs

Analogs of 5-amino-1-beta-D-ribofuranosylimidazole-4-carboxamide (AICA riboside) are provided which are useful in increasing extracellular levels of adenosine.

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.

SYNTHESIS OF 2-FORMYLADENOSINE USING DIETHOXYACETONITRILE AS A SYNTHON

Diethoxyacetonitrile has been utilized for the effective synthesis of adenine derivatives as a synthon.Novel 2-formyladenine (2b) and 2-formyladenosine (5b) have been prepared in high yields starting from AICN (1) and AICNR (4b), respectively.

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).