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Kibworth Harcourt, United Kingdom

Rodrigues F.A.R.,Federal University of Ceara | Bomfim I.D.S.,Federal University of Ceara | Cavalcanti B.C.,Federal University of Ceara | Pessoa C.,Federal University of Ceara | And 5 more authors.
Chemical Biology and Drug Design | Year: 2014

A series of 23 racemic mefloquine-oxazolidine derivatives, 4-[3-(aryl)hexahydro[1,3]oxazolo[3,4-a]pyridin-1-yl]-2,8-bis(trifluoromethyl) quinolines, derived from (R, S)-(±)-mefloquine and arenealdehydes, have been evaluated for their activity against four cancer cell lines (HCT-8, OVCAR-8, HL-60, and SF-295). Good cytotoxicities have been determined with IC50 values ranging from 0.59 to 4.79 μg/mL. In general compounds with aryl groups having strong electron-releasing substituents, such as HO and MeO, or electron-rich heteroaryl groups, for example imidazol-2-y-l, are active. However, other factors such as steric effects may play a role. As both the active and non-active conformations of the mefloquine-oxazolidine derivatives are similar, it is concluded that molecular conformations do not play a significant role either. This study is the first to evaluate mefloquine derivatives as antitumor agents. The mefloquine-oxazolidine derivatives are considered to be useful leads for the rational design of new antitumor agents. A series of twenty three racemic mefloquine-oxazolidine derivatives have been evaluated for their activity against 3-5 cancer cell lines SF-295, HCT-116, OVCAR-8, HCT-8 and HL-60. Cytotoxicities have been determined with IC 50 values ranging from 0.59 to 4.79 μg/mL. © 2013 John Wiley & Sons A/S. Source


Ferreira M.D.L.,Institute Tecnologia em Farmacos Farmanguinhos | De Souza M.V.N.D.,Institute Tecnologia em Farmacos Farmanguinhos | Wardell S.M.S.V.,CHEMSOL | Tiekink E.R.T.,University of Malaya
Acta Crystallographica Section E: Structure Reports Online | Year: 2012

In the title compound, C19H18ClN3O 3, the r.m.s. deviation through the 23 non-H and non-meth-oxy atoms is 0.088 Å, indicating a planar mol-ecule with the exception of the meth-oxy groups. One meth-oxy group, surrounded on either side by the other meth-oxy groups, is almost normal to the benzene ring to which it is connected [C-O-Car-Car torsion angle = 81.64 (15)°]. In the crystal, N-H⋯O, C-H⋯O and π-π inter-actions [between quinoline residues; centroid-centroid distance = 3.4375 (8) Å] link mol-ecules into a three-dimensional architecture. Source


De Souza M.V.N.,Institute Tecnologia em Farmacos Farmanguinhos | De Lima Ferreira M.,Institute Tecnologia em Farmacos Farmanguinhos | Wardell S.M.S.V.,CHEMSOL | Tiekink E.R.T.,University of Malaya
Acta Crystallographica Section E: Structure Reports Online | Year: 2012

In the nearly planar title compound (r.m.s. deviation for the 24 non-H atoms = 0.064 Å), C18H16ClN3O 2, the conformation about the N=C bond is E. Supra-molecular chains propagated by glide symmetry along [001] are found in the crystal packing. These are sustained by N-H⋯N hydrogen bonds with the quinoline N atom being the acceptor. The chains are connected into a three-dimensional architecture by π-π inter-actions involving all three aromatic rings [centroid-centroid distances = 3.5650 (9)-3.6264 (9) Å]. Source


Howie R.A.,University of Aberdeen | De Souza M.V.N.,Institute Tecnologia Em Farmacos Farmanguinhos R Sizenando | Ferreira M.D.L.,Institute Tecnologia Em Farmacos Farmanguinhos R Sizenando | Kaiser C.R.,Federal University of Rio de Janeiro | Wardell S.M.S.V.,CHEMSOL
Zeitschrift fur Kristallographie | Year: 2010

The molecules of the 7-chloroquinoline-4-hydrazones of the variously substituted benzaldehydes, 5, of general formula C16H 11ClN3X with X = H, o-F, m-F or m-MeO corresponding to compounds (5: X = H), (5: X = o-F), (5: X = m-F) and (5: X = m-MeO), respectively, are formally rather similar. Compounds (5: X = H) and (5: X = o-F) are isostructural but otherwise the molecular packing and intermolecular interactions show unexpectedly wide variation throughout the series. In all 5 hydrogenbonds link the essentially planar molecules edge to edge to form chains. Combination of intermolecular hydrogen-bonds and π⋯π interactions creates three-dimensional connectivity in (5: X = H), (5: X = o-F) and, utilising the methoxy oxygen atom as acceptor for a C-H⋯O hydrogen-bond, (5: X = m-MeO). Significant connectivity is no more than two-dimensional in layers of molecules in (5: X = m-F). © by Oldenbourg Wissenschaftsverlag, München. Source


Howie R.A.,University of Aberdeen | De Souza M.V.N.,Institute Tecnologia Em Farmacos Farmanguinhos R Sizenando | Pinheiro A.C.,Institute Tecnologia Em Farmacos Farmanguinhos R Sizenando | Kaiser C.R.,Federal University of Rio de Janeiro | Wardell S.M.S.V.,CHEMSOL
Zeitschrift fur Kristallographie | Year: 2011

The molecular structures of tert-butyl (S)-2-hydroxy-[N-(substituted- benzylidene)hydrazinyl-carbonyl]-ethylcarbamates, C15H 20N3O4X (3: X 1/4 H, o-OH, o-NO2, m-NO2 and p-CN), derived from L-serine, are formally rather similar. Despite the variation in substituent, X, triclinic (3: X 1/4 H), (3: X 1/4 o-OH), (3: X 1/4 m-NO2) and (3: X 1/4 p-CN) are isostructural and exhibit, with minor variations, the same fundamental intermolecular O-H-O and N-H-O hydrogen-bond connectivity in two-dimensions in layers of molecules. In monoclinic (3: X1/4 o-NO2), however, the oxygen atoms of the nitro group function as additional O-H-O and N-H-O hydrogen-bond acceptors resulting in a more complex form of two-dimensional connectivity. © by Oldenbourg Wissenschaftsverlag, München. Source

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