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Stratmann, Oliver; Hoppe, Dieter; Fröhlich, Roland

doi:10.1002/1521-3897(200010)342:8<828::aid-prac828>3.3.co;2-j

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2017

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“…There are few reports in the literature for the synthesis of the thiazolo[4,3- b ]oxazole system (Figure 2). Different intermediates were used for thiazolo[4,3- b ]oxazole preparation: azomethine ylides for (A) 11,12,13 vinylogous N -acyliminium ions for (B), 14 S -benzylthiocarbamates for (C) 15 or CS 2 for (D) 16 (figure 2). …”

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confidence: 99%

Enantioselective synthesis of new oxazolidinylthiazolidines as enzyme inhibitors

Saiz

Villamil

González

et al. 2017

Tetrahedron: Asymmetry

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The synthesis of new oxazolidinylthiazolidines bicycles, oxygen analogues of bisthiazolidines, also known as metallo-β-lactamase inhibitors is described. The reaction of β-aminoalcohols and 2,5-dihydroxy-1,4-dithiane led to oxazolidinylthiazolidines and/or dithia-azabicycles as the main products. The distribution pattern depends mainly on the aminoalcohol substituents. In a one-pot reaction, four new bonds are formed in good yields and with high atom efficiency. When the oxazolidinylthiazolidines are formed, two stereogenic centres are generated with high enantiospecificity. The reaction mechanism is discussed based on crystallographic data and interconversion studies. Two oxazolidinylthiazolidines were evaluated as inhibitors of the potent lactamase NDM-1 and compound 4f displayed competitive inhibition with Ki = 1.6 ± 0.6 µM.

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