Chemistry:2-Aminooxazole
2-Aminooxazole is a heterocyclic organic compound, belonging to the class of oxazoles. It is a five-membered ring structure containing one oxygen and two nitrogen atoms.
Properties
2-Aminooxazole contains a primary amine group which can participate in various reactions like protonation, acylation, or alkylation. The oxazole ring can also show reactions like ring expansion, electrophilic substitution, etc.[1] and also contributes aromatic character and stability to the molecule.
Applications
2-Aminooxazole possesses antimicrobial properties against various fungal and bacterial strains especially against Tuberculosis-causing Mycobacterium tuberculosis.[2]
The amine group of 2-Aminooxazole can potentially link with different molecules, making it a potential candidate for drug synthesis in antitubercular medicinal chemistry.[3]
2-Aminooxazole has also been hypothesised to have played a role in chemical evolution as a precursor of RNA nucleotides.[4]
See also
- Oxazoles
- 2-Aminothiazole
References
- ↑ Katritzky, Alan R.; Ramsden, Christopher A.; Joule, John A.; Zhdankin, Viktor V. (2010-08-24) (in en). Handbook of Heterocyclic Chemistry. Elsevier. ISBN 978-0-08-095844-6. https://books.google.com/books?id=7RglQV5yxKcC&q=aminooxazole&pg=PP1.
- ↑ Juhás, Martin; Bachtíková, Andrea; Nawrot, Daria Elżbieta; Hatoková, Paulína; Pallabothula, Vinod Sukanth Kumar; Diepoltová, Adéla; Janďourek, Ondřej; Bárta, Pavel et al. (2022-05-06). "Improving Antimicrobial Activity and Physico-Chemical Properties by Isosteric Replacement of 2-Aminothiazole with 2-Aminooxazole". Pharmaceuticals (MDPI AG) 15 (5): 580. doi:10.3390/ph15050580. ISSN 1424-8247. PMID 35631406.
- ↑ Azzali, Elisa; Girardini, Miriam; Annunziato, Giannamaria; Pavone, Marialaura; Vacondio, Federica; Mori, Giorgia; Pasca, Maria Rosalia; Costantino, Gabriele et al. (2020-07-09). "2-Aminooxazole as a Novel Privileged Scaffold in Antitubercular Medicinal Chemistry" (in en). ACS Medicinal Chemistry Letters 11 (7): 1435–1441. doi:10.1021/acsmedchemlett.0c00173. ISSN 1948-5875. PMID 32676151.
- ↑ Szabla, Rafał; Tuna, Deniz; Góra, Robert W.; Šponer, Jiří; Sobolewski, Andrzej L.; Domcke, Wolfgang (2013-08-15). "Photochemistry of 2-Aminooxazole, a Hypothetical Prebiotic Precursor of RNA Nucleotides" (in en). The Journal of Physical Chemistry Letters 4 (16): 2785–2788. doi:10.1021/jz401315e. ISSN 1948-7185. https://pubs.acs.org/doi/10.1021/jz401315e.
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