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Tiazofurin

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Chemical compound Pharmaceutical compound
Tiazofurin
Clinical data
Other names2--1,3-thiazole-4-carboxamide
ATC code
Identifiers
IUPAC name
  • (1R)-1--1,4-anhydro-D-ribitol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC9H12N2O5S
Molar mass260.26 g·mol
3D model (JSmol)
SMILES
  • O=C(c1nc(sc1)2O((O)2O)CO)N
InChI
  • InChI=1S/C9H12N2O5S/c10-8(15)3-2-17-9(11-3)7-6(14)5(13)4(1-12)16-7/h2,4-7,12-14H,1H2,(H2,10,15)/t4-,5-,6-,7-/m1/s1
  • Key:FVRDYQYEVDDKCR-DBRKOABJSA-N
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Tiazofurin is a drug which acts as an inhibitor of the enzyme IMP dehydrogenase. Tiazofurin and its analogues were under investigation for potential use in the treatment of cancer, though side effects such as pleuropericarditis and a flu-like syndrome precluded further development. They also show antiviral effects and may be reevaluated as potential options in the treatment of newly emerging viral diseases.

Synthesis

ChemDrug Synthesis:

The treatment of 1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (1) with trimethylsilyl cyanide gives 2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl cyanide (2). Treatment with hydrogen sulfide led to (2R,3R,4R,5R)-2-((Benzoyloxy)methyl)-5-carbamothioyltetrahydrofuran-3,4-diyl dibenzoate, PC10907289 (3). Cyclization with Ethyl bromopyruvate (4) led to 2-(2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl)-4-thiazolecarboxylic Acid Ethyl Ester (5). Removal of the protecting groups with sodium methoxide afforded 2-beta-D-Ribofuranosyl-4-thiazolecarboxylic Acid Ethyl Ester (6). Amide-ester interchange by treatment with dry ammonia completed the synthesis of Tiazofurin (7).

References

  1. Popsavin M, Torović L, Svircev M, et al. (2006). "Synthesis and antiproliferative activity of two new tiazofurin analogues with 2'-amido functionalities". Bioorg. Med. Chem. Lett. 16 (10): 2773–6. doi:10.1016/j.bmcl.2006.02.001. PMID 16495053.
  2. De Clercq E (March 2016). "C-Nucleosides To Be Revisited". Journal of Medicinal Chemistry. 59 (6): 2301–11. doi:10.1021/acs.jmedchem.5b01157. PMID 26513594.
  3. Eastland, G.; Tiazofurine. Drugs Fut 1985, 10, 4, 304.
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