3676-69-5

Basic information

• Product Name: 5-AMino-1-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-1H-iMidazole-4-carboxaMide
• Synonyms: 5-AMino-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)iMidazole-4-carboxaMide;5-AMino-1-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-1H-iMidazole-4-carboxaMide;5-Amino-1-[6-(hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]-1H-imidaz
• CAS NO: 3676-69-5
• Molecular Formula: C12H18N4O5
• Molecular Weight: 298.29512
• Product Categories: Carbohydrates & Derivatives, Nucleotides, Bases & Related Reagents
• Mol File: 3676-69-5.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: 5-AMino-1-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-1H-iMidazole-4-carboxaMide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMino-1-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-1H-iMidazole-4-carboxaMide(3676-69-5)
• EPA Substance Registry System: 5-AMino-1-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-1H-iMidazole-4-carboxaMide(3676-69-5)

Safety Data

• Hazardous Substances Data: 3676-69-5(Hazardous Substances Data)

Usage

Description

5-Amino-1-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-1H-imidazole-4-carboxamide, also known as A611700, is a nucleoside analogue derived from 5-aminoimidazole-4-carboxamide (AICAR). It has the ability to enter nucleoside pools and significantly increase adenosine levels during periods of ATP breakdown. 5-AMino-1-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-1H-iMidazole-4-carboxaMide is characterized by its unique chemical structure, which includes a 1-methylethylidene bridge between the 2' and 3' positions of the β-D-ribofuranosyl moiety, and an imidazole-4-carboxamide group at the 1-position.

Uses

Used in Cardioprotective Applications:
5-Amino-1-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-1H-imidazole-4-carboxamide is used as a cardioprotective agent for its ability to regulate adenosine levels in the body. Adenosine-regulating agents (ARAs) like A611700 have been recognized for their therapeutic potential in myocardial ischemia, a condition where the heart muscle doesn't receive enough blood and, consequently, oxygen. By increasing adenosine levels, A611700 can help protect the heart from damage during periods of ischemia and improve overall cardiac function.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-Amino-1-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-1H-imidazole-4-carboxamide is used as a key intermediate in the synthesis of various nucleoside analogues with potential therapeutic applications. Its unique chemical structure makes it a valuable building block for the development of new drugs targeting different diseases, including cancer and viral infections.
Used in Research and Development:
5-Amino-1-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-1H-imidazole-4-carboxamide is also used as a research tool in the field of biochemistry and molecular biology. It can be employed to study the mechanisms of nucleoside metabolism, adenosine signaling, and the role of these processes in various physiological and pathological conditions. Additionally, A611700 can be used to investigate the structure-activity relationships of nucleoside analogues and their potential as therapeutic agents.

Upstream product

• 659746-61-9 9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1-((2-methoxyethoxy)methyl)-1,9-dihydro-6H-purin-6-one 
• 659746-59-5 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(1-((2-methoxyethoxy)methyl)-6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 58-63-9 Inosine 
• 3181-38-2 2',3',5'-tri-O-acetylinosine 
• 924887-44-5 1-(2,4-dinitrophenyl)-2',3'-O-isopropylideneinosine 
• 2627-69-2 AICA riboside 
• 67-64-1 acetone 

Downstream Products

• 3031-95-6 (5-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-((phosphonooxy)methyl)tetrahydrofuran-2-yl)-1H-imidazole-4-carbonyl)-L-aspartic acid 
• 99592-68-4 [Carbamoyl-((3aR,4R,6R,6aR)-6-{(4-chloro-phenoxy)-[((Z)-octadec-9-enyl)oxy]-phosphoryloxymethyl}-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylcarbamoyl)-methyl]-carbamic acid tert-butyl ester 
• 99592-73-1 (Carbamoyl-{(3aR,4R,6R,6aR)-6-[(4-chloro-phenoxy)-hexadecyloxy-phosphoryloxymethyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylcarbamoyl}-methyl)-carbamic acid tert-butyl ester 
• 111543-48-7 Phosphoric acid (2R,3S,4R,5R)-5-(4-carbamoyl-5-hydroxy-imidazol-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 4-chloro-phenyl ester (Z)-octadec-9-enyl ester 
• 99592-75-3 Phosphoric acid (2R,3S,4R,5R)-5-(4-carbamoyl-5-hydroxy-imidazol-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 4-chloro-phenyl ester hexadecyl ester 
• 99592-69-5 Phosphoric acid (2R,3S,4R,5R)-5-(2-amino-2-carbamoyl-acetylamino)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 4-chloro-phenyl ester (Z)-octadec-9-enyl ester 
• 111543-47-6 Phosphoric acid (2R,3S,4R,5R)-5-(2-amino-2-carbamoyl-acetylamino)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 4-chloro-phenyl ester hexadecyl ester 
• 182494-75-3 1-[(3aR,4R,6R,6aR)-6-(1,3-Diphenyl-imidazolidin-2-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-5-ethynyl-1H-imidazole-4-carboxylic acid amide 
• 182494-74-2 1-[(3aR,4R,6R,6aR)-6-(1,3-Diphenyl-imidazolidin-2-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-5-ethynyl-1H-imidazole-4-carbonitrile 

Relevant articles and documents

Synthesis of N-1 and ribose modified inosine analogues on solid support

Herein, we report the synthesis and the use of new N-1-dinitrophenyl-inosine based solid supports, in which the C-2 of the purine base is strongly activated toward the attack of N-nucleophiles. The synthesized supports, binding the nucleoside by a 5′-O-monomethoxytrityl function, have been used to accomplish the synthesis of a small library of N-1 alkylated inosine and AICAR derivatives. In addition, cleavage of the 2′-3′ ribose bond of N-1 alkylated inosine derivatives anchored to the supports allowed to prepare a new set of N-1 alkylated-2′,3′-secoinosine derivatives in high yields.

Purines, pyrimidines, and imidazoles. XL. A new synthesis of a D-ribofuranosylamine derivative and its use in the synthesis of pyrimidine and imidazole nucleosides.

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