122970-40-5

Usage

Uses

Used in Pharmaceutical Industry:
7-thia-8-oxoguanosine is used as an immunomodulator for its ability to regulate cell growth by perturbing signal transduction pathways. This property makes it a valuable compound in the development of drugs targeting immune system-related conditions.
Used in Research and Development:
7-thia-8-oxoguanosine is used as a research tool for studying the effects of nucleoside modifications on cellular processes. Its unique structure allows scientists to investigate the role of specific molecular interactions in various biological pathways.
Used in Drug Design:
As a guanosine analogue, 7-thia-8-oxoguanosine is used in the design of novel therapeutic agents. Its immunostimulatory activity, as demonstrated by compounds like Isatoribine (brand name: Immusine), makes it a promising candidate for the development of new drugs with potential applications in treating various diseases, including cancer and autoimmune disorders.

InChI:InChI=1/C10H12N4O6S/c11-9-12-6-5(7(18)13-9)21-10(19)14(6)8-4(17)3(16)2(1-15)20-8/h2-4,8,15-17H,1H2,(H3,11,12,13,18)/t2-,3-,4-,8-/m1/s1

Upstream product

• 122970-39-2 5-amino-3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)thiazolo<4,5-d>pyrimidine-2,7(3H,6H)-dione 
• 14215-97-5 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose 
• 30161-97-8 5-aminothiazolo<4,5-d>pyrimidine-2,7(3H,6H)-dione 

Downstream Products

• 124737-24-2 5-Amino-3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)thiazolo[4,5-d]-pyrimidine-2,7(3H,6H)-dione 
• 533897-44-8 5-acetylamino-7-(2,4,6-triisopropyl-benzenesulfonyloxy)-3-(2,3,5-tri-O-acetyl-3-βD-ribofuranosyl)thiazolo[4,5-d]pyrimidin-2-one 

Relevant academic research and scientific papers

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.

Combined use of IMPDH inhibitors with toll-like receptor agonists

The present invention provides a broad-spectrum, long-lasting, and non-toxic combination of synthetic immunostimulatory agents, which are useful for activating the immune system of a mammal and treating diseases such as cancer and autoimmune disease. These agents include TLR-ligands and ligand analogs which induce interferon production, in combination with inhibitors of inosine monophosphate dehydrogenase (IMPDH), that further enhance the induction of interferon production.

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.

Thiazolo[4,5-d]pyrimidine nucleosides. The synthesis of certain 3-β-D-ribofuranosylthiazolo[4,5-d]pyrimidines as potential immunotherapeutic agents

Novel analogues of the naturally occurring purine nucleosides were synthesized in the thiazolo[4,5-d]pyrimidine ring system to determine the immunomodulatory effects of insertion of a sulfur atom in place of nitrogen at position 7 of the purine ring. In particular, 5-amino-3-β-D-ribofuranosylthiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dione (7, guanosine analogue), 3-β-D-ribofuranosylthiazolo[4,5-d]pyrimidine-2,5,7(3H,4H,6H)-trione (8, xanthosine analogue), 3-β-D-ribofuranosylthiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dione (10, inosine analogue), and 7-amino-3-β-D-ribofuranosylthiazolo[4,5-d]pyrimidine-2(3H)-one (32, adenosine analogue) were prepared, as well as the 8-mercaptoguanosine (14) and 6-mercaptoguanosine (17) analogues. Single-crystal X-ray studies confirmed the structural assignment of 17 and 32 as having the β-configuration with the site of glycosylation at N3. The nucleosides were evaluated for their ability to potentiate various murine immune functions in direct comparison to the known active agents 8-bromoguanosine (1), 8-mercaptoguanosine (2), and 7-methyl-8-oxoguanosine (3). Two of the guanosine analogues, 7 and 14, were found to exhibit significant immunoactivity relative to the positive control compounds (1-3), while the adenosine, inosine, xanthosine, and 6-mercaptoguanosine analogues were devoid of activity. Compound 7 exhibited greater immunoreactivity than any of the other guanosine analogues and derivatives in all test systems. Specifically, 7 was shown to be about twice as potent as 3 in the murine spleen cell mitogenicity assay. In addition, treatment with 7 produced about a 4-fold increase in natural killer cell cytotoxicity, while treatment with 3 afforded a 3-fold increase over controls. Finally, 7 provided excellent protection (92% survivors compared to 0% for placebo controls) against Semliki Forest virus in mice. Induction of interferon may account for the major mode of action of these guanosine analogues.

Antiviral methods utilizing ribofuranosylthiazolo[4,5-d]pyrimdine derivatives

Compounds of the structure: STR1 wherein R 1 and R 2 individually are H or C 1 -C 18 acyl and R 3 is H, C 1 -C 18 acyl or STR2 or R 1 is H and together R 2 and R 3 are STR3 and X is O or S, Y is --OH, --SH, --NH 2 or halogen, and Z is H, --NH 2, --OH or halogen, wherein halogen is Cl or Br, or a pharmaceutically acceptable salt thereof are useful as antivirals, antitumors and as immune system enhancers.