122970-43-8

Basic information

• Product Name: 7-THIO-8-OXOGUANOSINE
• Synonyms: 7-THIO-8-OXOGUANOSINE;3-b-D-ribofuranosylthiazolo[4,5-d]pyrimidine-2,7-(3H,6H)-dione;7-Thia-8-oxoguanosine;8-Oxo-7-thio-D-guanosine;3--D-ribofuranosylthiazolo[4,5-d]pyrimidine-2,7-(3H,6H)-dione;8-Oxo-7-thioguanosine
• CAS NO: 122970-43-8
• Molecular Formula: C10H11N3O6S
• Molecular Weight: 301.27584
• Product Categories: Bases & Related Reagents;Nucleotides
• Mol File: 122970-43-8.mol

Chemical Properties

• Melting Point: >255°C (dec.)
• Appearance: /
• Refractive Index: 2.004
• Storage Temp.: -20°C Freezer
• Solubility: DMSO, Water
• CAS DataBase Reference: 7-THIO-8-OXOGUANOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-THIO-8-OXOGUANOSINE(122970-43-8)
• EPA Substance Registry System: 7-THIO-8-OXOGUANOSINE(122970-43-8)

Safety Data

• Hazardous Substances Data: 122970-43-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-THIO-8-OXOGUANOSINE is used as a key compound for the development of antiviral, antitumor, and immune system enhancing nucleoside and nucleotide analogs. Its unique structure allows it to interact with biological targets, potentially leading to the creation of novel therapeutic agents.
Used in Antiviral Applications:
In the field of antiviral research, 7-THIO-8-OXOGUANOSINE serves as a valuable starting point for the design and synthesis of new antiviral drugs. Its ability to interact with viral targets can help in the development of treatments for various viral infections, including those caused by RNA and DNA viruses.
Used in Antitumor Applications:
7-THIO-8-OXOGUANOSINE is utilized as a building block for the synthesis of antitumor agents. Its incorporation into nucleoside and nucleotide analogs can lead to the development of drugs that target cancer cells, potentially offering new treatment options for patients with various types of cancer.
Used in Immune System Enhancement:
7-THIO-8-OXOGUANOSINE is also used in the development of compounds that can enhance the immune system's response to pathogens and other foreign substances. By modulating the immune system, these analogs can potentially improve the body's ability to fight off infections and diseases.

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

• 122970-42-7 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 
• 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 
• 30161-97-8 5-aminothiazolo<4,5-d>pyrimidine-2,7(3H,6H)-dione 

Relevant articles and documents

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.