Cvetkovski, Aleksandar (2024) Supramolecular hydrogen-bonding patterns of cocrystallized active pharmaceutical ingredient (API) phloroglucinol and N-heterocycles. In: From Molecules to Materials: 1st Workshop on Benchmarking Solid State Properties, 7-9 Sept 2024, Warsaw, Poland.
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Abstract
The active pharmaceutical ingredient phloroglucinol (PHL) has been taken as a drug model to explore the intermolecular interactions which can be established with other molecular entities to build PHL pharmaceutical cocrystals. From a supramolecular perspective, phloroglucinol PHL (1,3,5- trihydroxybenzene,) is a particularly attractive drug since it is rigid, i.e. it does not present torsional flexibility, and has three OH groups that can act as hydrogen-bonding donors and acceptors; from a chemical point of view, it can be classified as a weak acid (pKa value: 8.45). PHL is normally used as an antispasmodic agent. In addition, phloroglucinol and its derivatives exhibit a wide range of effects, such as anti-inflammatory, cytotoxicity, antithrombotic and profibrinolytic activities [1].
The crystal structures of five newly synthesized co-crystals are reported, where PHL is crystallized with N-heterocycles, namely 2-hydroxy-6-methylpyridine (1), 2,4-dimethyl-6-hydroxypyrimidine (2), 4-phenylpyridine (3), 2- hydroxypyridine (4) and 2,3,5,6-tetramethylpyrazine (5). The structural characteristics of these co-crystals, as far as the hydrogen-bonding networks and the crystalline architectures are concerned, are strongly dependent on the chemical features of the coformer molecules, as well as on their size and shape. A detailed analysis of the intermolecular interactions established in all the PHL co-crystals of known structures has allowed the recognition of some regularities in the packing modes that can be useful in the design of new supramolecular adducts forming predictable structural motifs [2].
References
[1] Barwell, C. J., et al., (1989). J. Appl.Phycol. 1, 319.
[2] Cvetkovski, A., et al., (2016). Acta Cryst. B72
| Item Type: | Conference or Workshop Item (Poster) |
|---|---|
| Subjects: | Medical and Health Sciences > Basic medicine Engineering and Technology > Chemical engineering Natural sciences > Chemical sciences Engineering and Technology > Nano-technology |
| Divisions: | Faculty of Medical Science |
| Depositing User: | Aleksandar Cvetkovski |
| Date Deposited: | 26 Sep 2024 11:00 |
| Last Modified: | 26 Sep 2024 11:00 |
| URI: | https://eprints.ugd.edu.mk/id/eprint/34714 |
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