13 research outputs found
(2S,3R)-tert-Butyl N-[4-(N-benzyl-4-fluorobenzenesulfonamido)-3-hydroxy-1-phenylbutan-2-yl]carbamate
In the title molecule, C28H33FN2O5S, the mean plane about the tertiary amine group (sum of the angles subtended at the sp
2-hybridized N atom = 359.7°) forms a dihedral angle of 16.66 (6)° with the phenyl ring adjacent to the carbamate group. The sulfonamide benzene ring and the hydroxy group lie to either side of the C2NS plane, whereas the benzylphenyl (connected to the N atom) and carbamate substituents lie to the other side. Supramolecular layers propagating in the ac plane are found in the crystal, linked by hydroxy–sulfonamide O—H⋯O and carbamate–carbamate N—H⋯O hydrogen bonds along with C—H⋯O and C—H⋯π interactions
Mefloquine–oxazolidine derivatives, derived from mefloquine and arenecarbaldehydes: In vitro activity including against the multidrug-resistant tuberculosis strain T113
AbstractTen new mefloquine–oxazolidine derivatives, 4-[(1S,8aR)-3-(aryl)hexahydro[1,3]oxazolo[3,4-a]pyridin-1-yl]-2,8-bis(trifluoromethyl)quinoline (1: aryl=substituted phenyl) and 4-[(1S,8aR)-3-(heteroaryl)hexahydro[1,3]oxazolo[3,4-a]pyridin-1-yl]-2,8-bis(trifluoromethyl)quinoline [2: heteroaryl=5-nitrothien-2-yl (2a); 5-nitrofuran-2-yl (2b) and 4H-imidazol-2-yl) (2c)], have been synthesized and evaluated against Mycobacterium tuberculosis. Compounds 1f (aryl=3-ethoxyphenyl), 1g (Ar=3,4,5-(MeO)3-C6H2) and 2c were slightly more active than mefloquine (MIC=33μM) with MICs=24.5, 22.5 and 27.4, respectively, whereas compounds 1e (aryl=3,4-(MeO)2-C6H3) and 2a (MICs=11.9 and 12.1μM, respectively) were ca. 2.7 times more active than mefloquine, with a better tuberculostatic activity than the first line tuberculostatic agent ethambutol (MIC=15.9). The compounds were also assayed against the MDR strain T113 and the same MICs were observed. Thus the new derivatives have advantages over such anti-TB drugs as isoniazid, rifampicin, ethambutol and ofloxacin, for which this strain is resistant. The most active compounds were not cytotoxic to Murine Macrophages Cells in a concentration near their MIC values
Different substituent effects on the supramolecular arrays in some (E)-halo- and nitro-benzaldehyde oximes : confirmation of attractive π(C=N)···π(phenyl) interactions
LRG thanks the Portuguese Foundation for Science and Technology (FCT) UID/Multi/04546/2013.for support.The crystal structures and Hirshfeld surface analyses are reported for four aldoximes, (E)-X–C6H4CH=N–OH [X = 3-Cl (1), 4-F (2), 2-O2N (3) and 4-O2N (4)]. The strong classical O–H · · · N hydrogen bonds involving the oxime group generate C(3) chains in compound 1, in contrast to the R22(6) dimers formed in compounds 2–4; such arrangements have been shown to be the most frequently found for oximes other than salicylaldoximes (2-hydroxybenzaldehyde oximes). In general, weaker intermolecular interactions involving the X substituents, as well as C–H · · · O and π · · · π interactions have significant effects on the supramolecular arrays generated in the aggegation. A further important interaction in compound 1, and to a lesser extent in compound 4, is a π(C=N) · · · π(phenyl) molecular stacking. A data base search has indicated that short Cg(C=N) · · · Cg(phenyl) distances, <3.3 Å (Cg = centre of gravity), have been found in various compounds, including other oximes. A theoretical study was carried out starting from the crystal structure data of compound 1, with optimisation at the BLYP-D3/def2-DZVP level, as well as at the higher PBE0/ma-def2-TZVP level. Breakdown of the interaction energy into separate contributions was achieved using SAPT (using the jun-cc-pvdz basis set). Overall, the calculations indicate that the π(C=N) ·· · π(phenyl) interaction is attractive, with a magnitude of 14–18 kJ mol−1.Publisher PDFPeer reviewe
Different substituent effects on the supramolecular arrays in some (E)-halo- and nitro-benzaldehyde oximes (crystallography data)
Supplementary crystallographic data available at the The Cambridge Crystallographic Data Centre: CCDC 1846653-1846655, and 1856711