English
Structure via PubChem · Public domain (PubChem)
tiazofurin
Sign in to saveAlso known as riboxamide, 2-(beta-D-ribofuranosyl)-4-thiazolecarboxamide, CI-909, TCAR, 2-beta-D-ribofuranosyl-4-thiazolecarboxamide
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== [[File:Tiazofurin synthesis.svg|thumb|center|500px|ChemDrug Synthesis:]] The treatment of 1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose [6974-32-9] (1) with trimethylsily
Chemical data
- Formula
- C9H12N2O5S
- Molecular weight
- 260.27 g/mol
- IUPAC name
- 2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-thiazole-4-carboxamide
- SMILES
- C1=C(N=C(S1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)N
- InChIKey
- FVRDYQYEVDDKCR-DBRKOABJSA-N
- XLogP
- -1.7
- Polar surface area
- 154 Ų
- H-bond donors
- 4
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- neoplasm
via ChEMBL · EBI
Wikidata facts
- Mass
- 260.047
Show 4 more facts
- chemical formula
- C₉H₁₂N₂O₅S
- isomeric SMILES
- C1=C(N=C(S1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)N
- canonical SMILES
- C1=C(N=C(S1)C2C(C(C(O2)CO)O)O)C(=O)N
- World Health Organisation international non-proprietary name
- tiazofurine
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
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== [[File:Tiazofurin synthesis.svg|thumb|center|500px|ChemDrug Synthesis:]] The treatment of 1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose [6974-32-9] (1) with trimethylsilyl cyanide gives 2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl cyanide [23316-67-8] (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 [70-23-5] (4) led to 2-(2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl)-4-thiazolecarboxylic Acid Ethyl Ester [60084-09-5] (5). Removal of the protecting groups with sodium methoxide afforded 2-beta-D-Ribofuranosyl-4-thiazolecarboxylic Acid Ethyl Ester [95936-53-1] (6). Amide-ester interchange by treatment with dry ammonia completed the synthesis of Tiazofurin (7). ==References==
Category:Carboxamides Category:Ribosides Category:Thiazoles Category:Experimental cancer drugs
Excerpted from Wikipedia’s “tiazofurin” article, available under the CC BY-SA 4.0 licence.