Supramolecular complexes of dihydroazolopyrimidines with macrocyclic receptors: synthesis, rapid analysis, and evaluation
Abstract
One of the main challenges limiting the medical use of dihydroazolopyrimidine derivatives is their poor water solubility. However, this problem can be significantly reduced by binding to supramolecular receptors. In this study, we investigated the complexation of ethyl 5,7-dimethyl-4,7-dihydrotetrazolo[1,5- a ]pyrimidine-6-carboxylate (DHP1) and ethyl 5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5- a ]pyrimidine-6-carboxylate (DHP2) with macrocyclic receptors: cucurbit[7]uril (CB7), β-cyclodextrin (β-CD), γ-cyclodextrin (γ-CD), and their modified derivatives, per-6-[(2-hydroxyethyl)amino]-6-deoxy-β-cyclodextrin (HEA-β-CD) and per-6-[(2-hydroxyethyl)amino]-6-deoxy-γ-cyclodextrin (HEA-γ-CD), in both solid and liquid phases. A quantitative high-performance liquid chromatography (HPLC) procedure for determining both DHPs in liquid systems was developed. The influence of time, temperature, and molar ratio CB7:DHPs on binding efficiency were systematically examined. Formation of the inclusion complexes was confirmed by thermogravimetric analysis (TGA) and powder X-ray diffraction (XRD) in the solid state and by HPLC in liquid media. It was demonstrated that the solubility of both DHPs in water increases through interaction with CB7. Furthermore, modification of CDs increases their binding affinity to DHP2.
Versions
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BibTeX
@article{miasnikova2026supramolecular,
title = {{Supramolecular complexes of dihydroazolopyrimidines with macrocyclic receptors: synthesis, rapid analysis, and evaluation}},
author = {Daria Miasnikova and Vyacheslav Saraiev and Olena Shvets and Anna Korobka and Olena Chernyaeva and Yana Sakhno and Olga Vashchenko and Anna Shaposhnyk and Valentyn A Chebanov},
journal = {Beilstein Journal of Organic Chemistry},
year = {2026},
month = oct,
doi = {10.3762/bjoc.22.122},
url = {https://www.beilstein-journals.org/bjoc/articles/22/122},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Supramolecular complexes of dihydroazolopyrimidines with macrocyclic receptors: synthesis, rapid analysis, and evaluation
AU - Daria Miasnikova
AU - Vyacheslav Saraiev
AU - Olena Shvets
AU - Anna Korobka
AU - Olena Chernyaeva
AU - Yana Sakhno
AU - Olga Vashchenko
AU - Anna Shaposhnyk
AU - Valentyn A Chebanov
PY - 2026
DA - 2026/10/29
JO - Beilstein Journal of Organic Chemistry
DO - 10.3762/bjoc.22.122
UR - https://www.beilstein-journals.org/bjoc/articles/22/122
AB - One of the main challenges limiting the medical use of dihydroazolopyrimidine derivatives is their poor water solubility. However, this problem can be significantly reduced by binding to supramolecular receptors. In this study, we investigated the complexation of ethyl 5,7-dimethyl-4,7-dihydrotetrazolo[1,5- a ]pyrimidine-6-carboxylate (DHP1) and ethyl 5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5- a ]pyrimidine-6-carboxylate (DHP2) with macrocyclic receptors: cucurbit[7]uril (CB7), β-cyclodextrin (β-CD), γ-cyclodextrin (γ-CD), and their modified derivatives, per-6-[(2-hydroxyethyl)amino]-6-deoxy-β-cyclodextrin (HEA-β-CD) and per-6-[(2-hydroxyethyl)amino]-6-deoxy-γ-cyclodextrin (HEA-γ-CD), in both solid and liquid phases. A quantitative high-performance liquid chromatography (HPLC) procedure for determining both DHPs in liquid systems was developed. The influence of time, temperature, and molar ratio CB7:DHPs on binding efficiency were systematically examined. Formation of the inclusion complexes was confirmed by thermogravimetric analysis (TGA) and powder X-ray diffraction (XRD) in the solid state and by HPLC in liquid media. It was demonstrated that the solubility of both DHPs in water increases through interaction with CB7. Furthermore, modification of CDs increases their binding affinity to DHP2.
SN - 1860-5397
ER -