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- Nestor, Stephen T., et al.
(författare)
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Studies on solubility and S-alkylation of 2-thiouracil in ionic liquids
- 2018
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Ingår i: Journal of Molecular Liquids. - : Elsevier. - 0167-7322 .- 1873-3166. ; 265, s. 463-467
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Tidskriftsartikel (refereegranskat)abstract
- Ionic liquids have been exploited to assist dissolution of poorly soluble (and poorly bioavailable) drugs, enhancing permeation through physiological barriers to deliver drugs to target sites. Herein, the solubility of 6-methyl-2-thiouracil - a common antithyroid drug, with low solubility in water and common organic solvents- was studied by employing six different imidazolium-based ionic liquids with variable anions. We demonstrate facile, regiospecific S-alkylation of 2-thiouracil with various lipophilic side chains in high yields (91-94%) and in the absence of catalysts. The reaction yields are correlated with the H-bond formation ability between the ILs' anions and the solute, indicating that the hydrogen bond is perhaps responsible for the high solubility of 2-thiouracil in [C(2)mim][OAc] and [C(2)mim][Cl].
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