52663-90-8

Usage

Chemical Properties

Colourless Syrup

Uses

Protected Ribavirin.

Upstream product

• 77-76-9 2,2-dimethoxy-propane 
• 36791-04-5 ribavirin 
• 67-64-1 acetone 
• 122-51-0 orthoformic acid triethyl ester 
• 79437-71-1 Amino(2,3-O-isopropyliden-D-ribofuranosylhydrazono)essigsaeure-ethylester 
• 79437-74-4 1-(2,3-O-Isopropyliden-β-D-ribofuranosyl)-1H-1,2,4-triazol-3-carbonsaeure-ethylester 

Downstream Products

• 52663-91-9 1-[5,5-(N,N'-diphenyl-N,N'-ethane-1,2-diyl-diamino)-O²,O³-isopropylidene-β-D-5-deoxy-ribofuranosyl]-1H-[1,2,4]triazole-3-carboxylic acid amide 
• 36791-04-5 ribavirin 
• 1246280-90-9 phosphoric acid ((3aR,4R,6R,6aR)-6-(3-carbamoyl-[1,2,4]-triazol-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl) ester 2-{[5-cyclopropyl-2-(4-fluorophenyl)-3-methylcarbamoylbenzofuran-6-yl]methanesulfonylamino}ethyl ester 
• 1246280-93-2 C₃₇H₄₁FN₆O₁₂S 
• 120615-22-7 1-(5'-O-sulfamoyl-β-D-ribofuranosyl)<1,2,4>triazole-3-carboxamide 

Relevant academic research and scientific papers

Synthesis and Evaluation of Bile Acid-Ribavirin Conjugates as Prodrugs to Target the Liver

Ribavirin is used to treat hepatitis C but causes serious hemolytic anemia. The objective of the study was to develop a ribavirin prodrug to achieve liver-specific drug delivery and to reduce its off-target effect in red blood cells (RBCs). The approach aimed to target the human sodium taurocholate cotransporting polypeptide (NTCP), which is a bile acid transporter predominately expressed in the liver. Six prodrugs with ribavirin conjugation at C-3 or C-24 of the bile acids were synthesized. In vitro uptake studies indicated that all six prodrugs were NTCP substrates. Metabolic studies in vitro indicated that ribavirin-l-Val-glycochenodeoxycholic acid (GCDCA) was able to release ribavirin in the mouse liver S9 fraction. Additionally, in vitro studies showed that ribavirin in RBC was reduced by 16.7-fold from prodrug compared with parent drug incubation. Moreover, almost no prodrug was present in RBC. In vivo study in mice also showed that ribavirin-l-Val-GCDCA could provide almost the same ribavirin exposure in the liver as ribavirin administration, but with about 1.8-fold less exposure of ribavirin in RBC, plasma, and kidney. Overall, the study suggested that ribavirin-l-Val-GCDCA has the potential to achieve ribavirin-specific liver delivery.

MODULATION OF IMMUNE CELLS

Disclosed are immune cell-selective small molecule IMPDH inhibitor compounds and methods of their synthesis and use to treat proliferative disorders.

Ribavirin semi-antigen and artificial antigen and its preparation method and application (by machine translation)

The invention relates to ribavirin semi-antigen and artificial antigen and its preparation method and application. The ribavirin semi-antigen having a structure of formula (I) or formula (II) as shown: The ribavirin artificial antigen is represented by t

Oligomer conjugates of heteropentacyclic nucleosides

The invention provides small molecule drugs that are chemically modified by covalent attachment of a water-soluble oligomer.

Design and synthesis of HCV agents with sequential triple inhibitory potentials

The union of HCV-796, a potent selective HCV NS5B polymerase inhibitor, and Ribavirin, a molecule with activities against a wide spectrum of viruses, resulted in a class of new anti-HCV agents with a sequential triple inhibitory mechanism.

PRODRUGS OF RIBAVIRIN WITH IMPROVED HEPATIC DELIVERY

The present invention relates ribavirin delivery systems and more specifically to compositions that comprise amino acids, as single amino acids or peptides, covalently attached to ribavarin and methods for administering conjugated ribavirin compositions.

Synthesis of triazole nucleoside derivatives

5′-O-Mesyl-2′,3′-O-isopropylidene ribonucleosides (4 and 12) were converted to their 5′-substituted nucleosides in good yields by reacted with NaN3 or KI. 2′,3′-O-Isopropylidene ribonucleosides (3 and 11) were prepared in good yields from ribonucleosides 1 and 2 with a reaction mixture of acetone and triethyl orthoformate instead of using acetone diethyl acetal. Compound 1 or 2 was treated with 2-acetoxyisobutyryl halide (Cl or Br) to give 1-[2-O-acetyl-3-halo-3-deoxy-5-O-(2,5,5-trimethyl-1,3-dioxolan-4-on-2-yl)- β-D-xylofuranosyl]-1,2,4-triazole-3-carboxamide (19, 22, and 23) in high yields. Instead of using 2-acetoxyisobutyryl bromide, the mixture of 2-acetoxyisobutyryl chloride and NaBr was employed in the synthesis of 22 and 23. Treatment of 19 with an activated Zn/Cu couple and deprotection gave 2′,3′-anhydro nucleoside (21), and treatment of 22 and 23 with an activated Zn/Cu couple and a little of HOAc and deprotection gave corresponding 2′,3′-unsaturated triazole nucleosides (24 and 25), respectively. The biological activity of the compounds (7～10, 15～18, and 24) was examined in human liver cancer cells (A-549), lung cancer cells (BEL-7402), and Flu-A cells.

Synthesis, Structure, and Antiparasitic Activity of Sulfamoyl Derivatives of Ribavirin

The triazole nucleoside derivatives 1-(5'-O-sulfamoyl-β-D-ribofuranosyl)triazole-3-carboxamide (2), 1-(5'-O-sufamoyl-β-D-ribofuranosyl)triazole-3-thiocarboxamide (3), and 1-(5'-O-sulfamoyl-β-D-ribofuranosyl)triazole-3-carbonitrile (4) were synthesized.Suitable protected triazole nucleosides were converted to their corresponding 5'-sulfamoyl derivatives, which on subsequent deprotection gave the desired compounds in good yields.The structures of compounds 2-4 were confirmed by X-ray crystallographic analysis.All three compounds showed significant activity in vitro, while 2 showed significant activity in vivo against Leishmania donovani and Trypanosoma brucei.