2-Aminooxazole Explained

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

Notes and References

  1. Book: Katritzky . Alan R. . Handbook of Heterocyclic Chemistry . Ramsden . Christopher A. . Joule . John A. . Zhdankin . Viktor V. . 2010-08-24 . Elsevier . 978-0-08-095844-6 . en.
  2. Juhás . Martin . Bachtíková . Andrea . Nawrot . Daria Elżbieta . Hatoková . Paulína . Pallabothula . Vinod Sukanth Kumar . Diepoltová . Adéla . Janďourek . Ondřej . Bárta . Pavel . Konečná . Klára . Paterová . Pavla . Šesták . Vít . Zitko . Jan . Improving Antimicrobial Activity and Physico-Chemical Properties by Isosteric Replacement of 2-Aminothiazole with 2-Aminooxazole . Pharmaceuticals . MDPI AG . 15 . 5 . 2022-05-06 . 1424-8247 . 10.3390/ph15050580 . free . 580. 35631406 . 9143880 .
  3. Azzali . Elisa . Girardini . Miriam . Annunziato . Giannamaria . Pavone . Marialaura . Vacondio . Federica . Mori . Giorgia . Pasca . Maria Rosalia . Costantino . Gabriele . Pieroni . Marco . 2020-07-09 . 2-Aminooxazole as a Novel Privileged Scaffold in Antitubercular Medicinal Chemistry . ACS Medicinal Chemistry Letters . en . 11 . 7 . 1435–1441 . 10.1021/acsmedchemlett.0c00173 . 1948-5875 . 7357219 . 32676151.
  4. 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 . The Journal of Physical Chemistry Letters . en . 4 . 16 . 2785–2788 . 10.1021/jz401315e . 1948-7185.

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