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Tiazofurine

Tiazofurine
Image illustrative de l’article Tiazofurine
Structure de la tiazofurine
Identification
Nom UICPA 2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxyméthyl)oxolan-2-yl]-1,3-thiazole-4-carboxamide
Synonymes

(1R)-1,4-anhydro-1-(4-carbamoyl-1,3-thiazol-2-yl)-D-ribitol

No CAS
Code ATC L01XX18
PubChem 457954
ChEBI 90239
SMILES
InChI
Propriétés chimiques
Formule C9H12N2O5S  [Isomères]
Masse molaire[1] 260,267 ± 0,015 g/mol
C 41,53 %, H 4,65 %, N 10,76 %, O 30,74 %, S 12,32 %,
Propriétés physiques
Solubilité soluble dans l'eau[2]
Propriétés optiques
Indice de réfraction = -13,8 ± 2 (cc = 0.914, DMF)[2]
Spectre d’absorption (95% ethanol) max = 236 ± 2 nm E = 7,660 - 7,970[2]
Écotoxicologie
DL50 1 684 mg/kg (souris, i.p.)[3]
3 400 mg/kg (souris, i.v.)[3]
LogP (octanol/eau) -1,73[3]

Unités du SI et CNTP, sauf indication contraire.

La tiazofurine est un inhibiteur de l'IMP déshydrogénase. Cette molécule et ses analogues ont fait l'objet de recherches pour d'éventuelles applications dans le traitement de certains cancers[4],[5].

Notes et références

  1. Masse molaire calculée d’après « Atomic weights of the elements 2007 », sur www.chem.qmul.ac.uk.
  2. a b et c PubChem CID457954
  3. a b et c (en) « Tiazofurine », sur ChemIDplus.
  4. (en) Mirjana Popsavin, Ljilja Torović, Miloš Svirčev, Vesna Kojić, Gordana Bogdanović et Velimir Popsavin, « Synthesis and antiproliferative activity of two new tiazofurin analogues with 2′-amido functionalities », Bioorganic & Medicinal Chemistry Letters, vol. 16, no 10,‎ , p. 2773-2776 (PMID 16495053, DOI 10.1016/j.bmcl.2006.02.001, lire en ligne)
  5. (en) Theodore J. Boritzki, David A. Berry, Judith A. Besserer, P. Dan Cook, David W. Fry, Wilbur R. Leopold et Robert C. Jackson, « Biochemical and antitumor activity of tiazofurin and its selenium analog (2-β-D-ribofuranosyl-4-selenazolecarboxamide) », Biochemical Pharmacology, vol. 34, no 7,‎ , p. 1109-1114 (PMID 3985993, DOI 10.1016/0006-2952(85)90617-3, lire en ligne)
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Tiazofurine
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