2-Aminothiazole

changed changed 403351202 2-Aminothiazole.svg 150px Skeletal formula of aminothiazole 2-Aminothiazole-3D-spacefill.png 140 Space-filling model of the aminothiazole molecule 1,3-Thiazol-2-amine 2-Thiazolamine, Aminothiazole, 2-Thiazylamine, Basedol, 2-Thiazolylamine, 4-Thiazolin-2-onimine, 2-Amino-1,3-thiazole, Abadole correct CAS 96-50-4 correct chemspider 2070 correct EBI 40782 correct EBI 344760 202-511-6 2155 correct kegg D02479 correct FDA 5K8WKN668K 1/C3H4N2S/c4-3-5-1-2-6-3/h1-2H,(H2,4,5) RAIPHJJURHTUIC-UHFFFAOYAZ correct chemspider 1S/C3H4N2S/c4-3-5-1-2-6-3/h1-2H,(H2,4,5) correct chemspider RAIPHJJURHTUIC-UHFFFAOYSA-N c1csc(n1)N 3 4 2 1 Light yellow crystals 86 to 89 117 (20 hPa) 100 g/L (20 °C) −56.0·10−6 cm3/mol 600 2 0 0 2-Aminothiazole https://pubchem.ncbi.nlm.nih.gov/compound/2155#section=Safety-and-Hazards pubchem.ncbi.nlm.nih.gov 12 December 2022 en 07 Warning 302 319 264 264+265 270 280 301+317 305+351+338 330 337+317 501 2-Aminothiazole is a heterocyclic amine featuring a thiazole core. It can also be considered a cyclic isothiourea. It possesses an odor similar to pyridine and is soluble in water, alcohols and diethyl ether. 2-Aminothiazole itself is mainly of academic interest, with few exceptions. It is a precursor to a sulfathiazole ("sulfa drugs"). 2-Aminothiazole can be used as a thyroid inhibitor in the treatment of hyperthyroidism.10.1002/14356007.a27_039 Thyrotherapeutic Agents Ullmann's Encyclopedia of Industrial Chemistry 2000 Dahlmanns Simone M. Müller-Gärtner Hans-Wilhelm 978-3-527-30385-4 2-Aminothiazole is prepared from paraldehyde, thiourea, and sulfuryl chloride.10.1002/hlca.19550380529 Zur Synthese von 2-Amino-thiazolderivaten 1955 Erlenmeyer H. Herzfeld L. Prijs B. Helvetica Chimica Acta 38 5 1291–1294 2-Aminothiazoles Like the parent, 2-aminothiazoles are often produced by the condensation of thiourea and an alpha-halo ketone. 2-Amino-4-methylthiazole J. R. Byers J. B. Dickey 1939 19 10 10.15227/orgsyn.019.001010.15227/orgsyn.091.0185 Synthesis of 4,5-Disubstituted 2-Aminothiazoles from α,β-Unsaturated Ketones: Preparation of 5-Benzyl-4-methyl-2-aminothiazolium Hydrochloride Salt 2014 Gómez Antonio Bermejo Nanna Ahlsten Ana E. Platero-Prats Belén Martín-Matutejournal=Organic Syntheses Organic Syntheses 91 185–200 free On the [2+2] Cycloaddition of 2-Aminothiazoles and Dimethyl Acetylenedicarboxylate. Experimental and Computational Evidence of a Thermal Disrotatory Ring Opening of Fused Cyclobutenes Alajarín, M. Cabrera, J. Pastor, A. Sánchez-Andrada, P. Bautista, D. J. Org. Chem. 2006 71 14 5328–5339 10.1021/jo060664c 16808523 left|500px|Hantsch Thiazole Synthesis In an adaptation of the Robinson-Gabriel synthesis, a 2-acylamino-ketone reacts with phosphorus pentasulfide. Applications Synthetic aminothiazoles - compounds containing the parent 2-aminothiazole as a subunit - are used in medicinal chemistry. Some examples are abafungin, acotiamide, amiphenazole, amthamine, avatrombopag, aztreonam, cefepime, cefixime, ceftizoxime, ceftiofur, ceftibuten, cefpirome, famotidine, meloxicam, and pramipexole.10.1016/j.ejmech.2015.12.022 Recent Developments of 2-Aminothiazoles in Medicinal Chemistry 2016 Das Debasis Sikdar Papiya Bairagi Moumita European Journal of Medicinal Chemistry 109 89–98 26771245 10.1016/j.ejmech.2020.112953 2-Aminothiazole: A privileged scaffold for the discovery of anti-cancer agents 2021 Wan Yichao Long Jiabing Gao Han Tang Zilong European Journal of Medicinal Chemistry 210 112953 33148490 226258989 See a related compound called 2-Amino-2-thiazoline [1779-81-3].Castañer, J. Gosálvez, M. Drugs of the Future 2-Amino-2-thiazoline hydrochloride 8 12 1005 1983 0377-8282 10.1358/dof.1983.008.12.1003509 References Category:Aromatic amines Category:2-Thiazolyl compounds