5-Iodouridine

Chemical Properties

White powder

Uses

5-Iodouridine has shown to enhance the effect of gamma irradiation in hamster cells. It is used as catalytic agent, petrochemical additive, used in organic synthesis.

Synthesis

The general procedure for the synthesis of 5-iodouridine from 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione was carried out as follows: in a round-bottomed flask, uracil (1 g, 4.1 mmol) and iodine (1.15 g, 4.5 mmol) were dissolved in a mixture of chloroform (55 ml) and 1M Nitric acid (10 ml) in a mixed solution. The reaction mixture was heated to 80°C and refluxed for 5 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and the unfolding agent was a chloroform solution of 30% methanol (Rf: 0.60; raw material Rf: 0.45). After completion of the reaction, the mixture was cooled to 4 °C and colorless needle-like 5-iodouridine crystals were precipitated. The precipitate was collected by filtration and dried under vacuum overnight to give 1.39 g of 5-iodouridine in 92% yield. The product was subjected to nuclear magnetic resonance hydrogen (1H NMR, DMSO-d6, 300 MHz) and carbon (13C NMR, DMSO-d6, 300 MHz) spectra to confirm the structure, and mass spectrometry (ESI) showed that the molecular ion peak [M+NH4]+ was 388.0000, which was consistent with the theoretical value.

Purification Methods

Recrystallise 5iodouridine from H2O and dry it in vacuo at 100o. UV has max 289nm (0.01N HCl) and 278nm (0.01N NaOH). [Prusoff et al. Cancer Res 13 221 1953, Beilstein 24 III/IV 1235.]

References

[1] Bulletin of the Korean Chemical Society, 2018, vol. 39, # 9, p. 1054 - 1057
[2] Synthetic Communications, 1990, vol. 20, # 21, p. 3391 - 3394
[3] Canadian Journal of Chemistry, 1994, vol. 72, # 9, p. 2005 - 2010
[4] Patent: WO2011/51733, 2011, A2. Location in patent: Page/Page column 44
[5] Synthesis, 2009, # 23, p. 3957 - 3962
[6] EDWARD BRESNICK  Karen B. Inhibition of dihydroorotase by purines and pyrimidines[J]. Biochimica et Biophysica Acta (BBA) - Specialized Section on Enzymological Subjects, 1964, 81 1: Pages 150-157. DOI: 10.1016/0926-6569(64)90345-1
[7] Y KURODA  T K  A Yokoiyama. Radiosensitization of cultured mammalian cells by 5-iodouridine.[J]. International journal of radiation biology and related studies in physics, chemistry, and medicine, 1975, 27 3: 247-257. DOI: 10.1080/09553007514551541
[8] RAKESH KUMAR. Synthesis and antiviral and cytotoxic activity of iodohydrin and iodomethoxy derivatives of 5-vinyl-2’-deoxyuridines, 2’-fluoro-2’-deoxyuridine, and uridine[J]. Journal of Medicinal Chemistry, 1990, 33 2: 717-723. DOI: 10.1021/jm00164a039