Mefloquine derivatives: Crystal structures and anti-tubercular activities of diphenyl[((R*,S*)-2,8-bis(trifluoromethyl)quinolin-4-yl)-piperidin-2-yl-methanolato-O,N]boron and (±)-erythro-mefloquinium tetraphenylborate solvates
✍ Scribed by James L. Wardell; Marcus V.N. de Souza; Solange M.S.V. Wardell; Maria C.S. Lourenço
- Publisher
- Elsevier Science
- Year
- 2011
- Tongue
- English
- Weight
- 762 KB
- Volume
- 990
- Category
- Article
- ISSN
- 0022-2860
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✦ Synopsis
Thermolysis of (R Ã ,S Ã )-(2-{2,8-bis(trifluoromethyl)quinolin-4-yl$methyl}piperidin-1-ium) tetraphenylborate, (±)-erythro-mefloquinium tetraphenylborate, 3, in solution or neat, provides the oxazaborolidine derivative, diphenyl[(R Ã ,S Ã )-(2,8-bis(trifluoromethyl)quinolin-4-yl)]piperidin-2-yl-methanolato-O,N]boron, 2. Crystal structures of solvates of 2 and 3 are reported. As shown by the 1 H NMR spectrum, 2 undergoes a conformation equilibrium in solution. Both 2 and 3 exhibit important antitubercular activities as indicated by the minimum inhibitory concentrations (MIC) of 50 and 12.5 lg/ ml, respectively, in in vitro assays against M. tuberculosis H37Rv ATTC 27294.