124737-24-2

Basic information

• Product Name: 5-amino-3-(2,3,5-tri-O-acetyl-beta-ribofuranosyl)thiazolo(4,5-d)pyrimidine-2,7-dione
• Synonyms: 5-amino-3-(2,3,5-tri-O-acetyl-beta-ribofuranosyl)thiazolo(4,5-d)pyrimidine-2,7-dione
• CAS NO: 124737-24-2
• Molecular Formula: C₁₆H₁₈N₄O₉S
• Molecular Weight: 442.4
• Mol File: 124737-24-2.mol

Chemical Properties

• Boiling Point: 580.7°Cat760mmHg
• Flash Point: 305°C
• Appearance: /
• Density: 1.8g/cm³
• Vapor Pressure: 1.77E-13mmHg at 25°C
• Refractive Index: 1.726
• CAS DataBase Reference: 5-amino-3-(2,3,5-tri-O-acetyl-beta-ribofuranosyl)thiazolo(4,5-d)pyrimidine-2,7-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-amino-3-(2,3,5-tri-O-acetyl-beta-ribofuranosyl)thiazolo(4,5-d)pyrimidine-2,7-dione(124737-24-2)
• EPA Substance Registry System: 5-amino-3-(2,3,5-tri-O-acetyl-beta-ribofuranosyl)thiazolo(4,5-d)pyrimidine-2,7-dione(124737-24-2)

Safety Data

• Hazardous Substances Data: 124737-24-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H18N4O9S/c1-5(21)26-4-8-9(27-6(2)22)10(28-7(3)23)14(29-8)20-12-11(30-16(20)25)13(24)19-15(17)18-12/h8-10,14H,4H2,1-3H3,(H3,17,18,19,24)/t8-,9-,10-,14-/m1/s1

Upstream product

• 30161-97-8 5-aminothiazolo<4,5-d>pyrimidine-2,7(3H,6H)-dione 
• 39727-26-9 β-D-Ribofuranose-1,2,3,5-tetraacetate 
• 122970-40-5 7-thia-8-oxoguanosine 
• 108-24-7 acetic anhydride 
• 122970-40-5 isatoribine 

Relevant articles and documents

Discovery of ANA975: An oral prodrug of the TLR-7 agonist isatoribine

ANA975, a 5-amino-3-β-D-ribofuranosyl-3H-thiazolo[4,5-d]pyrimidin-2- one derivative, was synthesized in the search of an oral prodrug of isatoribine, a small molecule toll-like receptor 7 (TLR-7) agonist. Several strategies were studied to enable the kilogram-scale synthesis of ANA975. Three general total syntheses are described. In the phase I clinical study of ANA975 against hepatitis C virus (HCV), conversion to isatoribine in plasma was rapid and effective, delivering levels of isatoribine that have been shown to be clinically relevant. Copyright Taylor & Francis Group, LLC.

3-B-D-ribofuranosylthiazolo [4,5-d] pyridimine nucleosides and uses thereof

The invention is directed to 3-β-D-ribofuranosylthiazolo[4,5-d]pyridimine nucleosides and pharmaceutical compositions containing such compounds that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and compositions, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds.

3-β-D-RIBOFURANOSYLTHIAZOLO[4,5-d]PYRIDIMINE NUCLEOSIDES AND USES THEREOF

The invention is directed to 3-?-D-ribofuranosylthiazolo[4,5-d]pyridimine nucleosides and pharmaceutical compositions containing such compounds that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and compositions, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds.

Administration of TLR7 ligands and prodrugs thereof for treatment of infection by hepatitis C virus

This invention relates to methods for treating or preventing hepatitis C virus infections in mammals using Toll-Like Receptor (TLR)7 ligands and prodrugs thereof. More particularly, this invention relates to methods of orally administering a therapeutically effective amount of one or more prodrugs of TLR7 ligands for the treatment or prevention of hepatitis C viral infection. Oral administration of these TLR7 immunomodulating ligands and prodrugs thereof to a mammal provides therapeutically effective amounts and reduced undesirable side effects.

Immune system enhancing 3-β-d-ribofuranosylthiazolo[4,5-d]pyridimine nucleosides and nucleotides

Compounds of the structure: STR1 wherein R4, R5, R6 and R7 individually are H, OH or C1 -C18 O-acyl and R3 is H, C1 -C18 acyl or STR2 or R5 and R7 are H or OH, R6 is H and together R3 and R4 are STR3 and X is =O or =S; Y is --OH, --SH, --Nh2 or halogen; and Z is H , --Nh2, --OH or halogen; wherein halogen is Cl or Br; or pharmaceutically acceptable salt thereof are useful as antivirals, antitumors, antimetastatics and as immune system enhancers.

Synthesis and antiviral activity of certain guanosine analogues in the thiazolo[4,5-d]pyrimidine ring system

Several sugar-modified nucleoside derivatives of the purine analogue 5-amino-3-β-D-ribofuranosylthiazolo[4,5-d]-pyrimidine-2,7-dione (1) were synthesized. Phosphorylation of 1 using POCl3 resulted in 5'-monophosphate 2, which was subsequently converted to 3',5'-cyclic phosphate 3, by reported methods. 5'-Sulfamoyl derivative 4 was synthesized by treatment of the 2,3-O-isopropylidene derivative of 1 with chlorosulfonamide followed by acid deprotection. Compounds 5-7, the 5'-deoxy, the tri-O-acetyl, and the 2'-deoxy derivatives of 1, respectively, were synthesized by glycosylation of 5-aminothiazolo[4,5-d]pyrimidine-2,7-dione, the aglycon of 1, with the appropriate sugar moieties, utilizing the Vorbruggen procedure. Oxidative cleavage of the C(2')-C(3') bond in 1 followed by reduction with sodium borohydride led to ''seco'' analogue 8. Nucleosides 2-8 were evaluated for antiviral activity in vivo against the Semliki Forest virus. The activity of compounds 2, 5, and 7 were similar to that of 1. Cyclic phosphate 3 was toxic at the high dose and weakly active at the lower dose. Compounds 4, 6, and 8 were inactive in this system.