# 2-Allylaminothiazole and 2-allylaminodihydrothiazole derivatives: synthesis, characterization, and evaluation of bioactivity

**Authors:** Renata Studzińska, Aleksandra Karczmarska-Wódzka, Anna Kozakiewicz, Renata Kołodziejska, Renata Paprocka, Marcin Wróblewski, Beata Augustyńska, Bożena Modzelewska-Banachiewicz

PMC · DOI: 10.1007/s00706-015-1539-z · Monatshefte Fur Chemie · 2015-08-05

## TL;DR

This paper describes the synthesis and characterization of new thiazole and dihydrothiazole compounds with potential drug-like properties.

## Contribution

The study introduces new 2-allylaminothiazole and 2-allylaminodihydrothiazole derivatives with promising bioavailability and pharmacological potential.

## Key findings

- The compounds were synthesized with good yields using chlorooxoesters and 1-allylthiourea.
- Structures were confirmed using NMR and X-ray diffraction analysis.
- All compounds met the rule of five, indicating good oral absorption and potential drug properties.

## Abstract

Some reactions of selected chlorooxoesters and haloesters with a 1-allylthiourea under various conditions have been performed. The reactions have been performed in methanol in alkaline and neutral environment. Condensation of 1-allylthiourea with chlorooxoesters has been further led via acetal as intermediate compound. As a result, the compounds containing thiazole and a 4,5-dihydrothiazole ring with a good yield have been obtained. The structures of the compounds were verified by 1H NMR, 13C NMR as well as X-ray diffraction analysis. Due to the potential biological activity of the synthesized compounds, the parameters of their bioavailability have been determined, and the probability of pharmacological action has been defined. All of the obtained compounds fulfilled the rule of five, which indicate their good absorption after oral intake. The probability of pharmacological action and potential targets calculated for the obtained compounds show that they can be potential drugs.

## Linked entities

- **Chemicals:** 1-allylthiourea (PubChem CID 1549517), thiazole (PubChem CID 9256), dihydrothiazole (PubChem CID 151424)

## Full-text entities

- **Genes:** TYMS (thymidylate synthetase) [NCBI Gene 7298] {aka DKCD, HST422, TMS, TS}, GAST (gastrin) [NCBI Gene 2520] {aka GAS}
- **Diseases:** metabolic syndrome (MESH:D024821), type 2 diabetes (MESH:D003924)
- **Chemicals:** pyridine (MESH:C023666), thiourea (MESH:D013890), CHCl3 (MESH:D002725), sodium ethoxide (MESH:C098088), methanol (MESH:D000432), halogen (MESH:D006219), acetal (MESH:D000080), nitrogen (MESH:D009584), ammonia (MESH:D000641), sulfur (MESH:D013455), Cl (MESH:D002713), thiazole (MESH:D013844), aldol (MESH:C116609), np (MESH:D009405), ester (MESH:D004952), 1-allylthiourea (-), 13C (MESH:C000615229), hydrogen (MESH:D006859), 3H (MESH:D014316), H2O (MESH:D014867), 2H (MESH:D003903), sodium carbonate (MESH:C005686), benzene (MESH:D001554), H2SO4 (MESH:C033158), C (MESH:D002244), HCl (MESH:D006851), p-toluenesulfonic acid (MESH:C029501), isobutane (MESH:D002073), NaOH (MESH:D012972), Diethyl ether (MESH:D004986), acetonitrile (MESH:C032159), sodium (MESH:D012964), ethyl acetate (MESH:C007650), EtOH (MESH:D000431)
- **Species:** Homo sapiens (human, species) [taxon 9606]

## Full text

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## Figures

5 figures with captions in the complete paper: https://tomesphere.com/paper/PMC4559095/full.md

## References

19 references — full list in the complete paper: https://tomesphere.com/paper/PMC4559095/full.md

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Source: https://tomesphere.com/paper/PMC4559095