- Synthesis and in vitro antimycobacterial activity of compounds derived from (R)- and (S)-2-amino-1-butanol - The crucial role of the configuration
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The synthesis of 47 structurally diverse compounds incorporating the (R)-2-amino-1-butanol motif has been realized. Ten of these compounds were found to exhibit in vitro specific activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.65 μM-14.03 μM. Five of the most active compounds 11, 22, 23, 31 and 42 (5.7-11.1 fold more active than ethambutol) can be outlined with very low cytotoxicity towards human embryonal kidney non-tumour cells (SI ranging from 91.2 to 375.4). For the purpose of comparison the (S)-enantiomers of these most active compounds have been synthesized and evaluated towards M. tuberculosis H37Rv showing no activity even at 20-32 fold higher concentrations.
- Dobrikov, Georgi M.,Valcheva, Violeta,Stoilova-Disheva, Margarita,Momekov, Georgi,Tzvetkova, Pavleta,Chimov, Angel,Dimitrov, Vladimir
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supporting information; experimental part
p. 45 - 56
(2012/03/26)
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- Synthesis of chiral alcohols by asymmetric reductions of various ketones including α-aminophenones
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LiAlH4 previously treated with 2.5 equiv. of (S)-(+) or (R)-(-)-2-(2-isoindolinyl)butan-1-ol 1 reduced the six α-aminophenones 4-9 into the corresponding optically active β-aminoalcohols 10-15 whose ee's were in the range of 40-97% after chroma
- Brown, Eric,Leze, Antoine,Touet, Joel
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p. 2029 - 2040
(2007/10/03)
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- Determination of the Enantiomeric Excesses of Chiral Acids by 19F NMR Studies of their Esters deriving from (R)-(+)-2-(Trifluoromethyl)benzhydrol
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15-Chiral acids were esterified with optically pure (R)-(+)-2-(trifluoromethyl)benzhydrol (R)-(+)-1, a readily available reagent.With respect to the carboxy group, the stereogenic centre is in the β-position in the case of the acids 5a-10a and 12a-16a, and in the α position in the case of the acids 17a-20a.The diastereomeric excesses of the corresponding esters 5b-10b and 12b-20b, respectively, were easily determined by means of 19F NMR.These d.e. values were in very good agreement with the e.e. values of the corresponding acids when the latter were known compounds.
- Brown, Eric,Chevalier, Christelle,Huet, Francois,Grumelec, Christelle Le,Leze, Antoine,Touet, Joel
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p. 1191 - 1194
(2007/10/02)
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- ASSYMETRIC REDUCTIONS OF KETONES USING LITHIUM ALUMINIUM HYDRIDE MODIFIED WITH N,N-DIALKYL DERIVATIVES OF (R)-(-)-2-AMINOBUTAN-1-OL
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LiAlH4 previuosly treated with 2 equivalents of (R)-(-)-2-(2-iso-indolinyl)butan-1-ol (a readily available reagent) reduced 2-chloro and 2,4-dimethyl benzophenones into the corresponding benzhydrols with 100percent enantiomeric excess.Other examples of ketone reductions are given.
- Brown, Eric,Penfornis, Annie,Bayma, Joaquim,Touet, Joeul
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p. 339 - 342
(2007/10/02)
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