TY - JOUR
T1 - Synthesis, structural characterization and biological activity of fluorinated Schiff-bases of the type [C6H4-1-(OH)-3-(CHNArF)]
AU - Avila-Sorrosa, Alcives
AU - Hernández-González, Jorge Ignacio
AU - Reyes-Arellano, Alicia
AU - Toscano, Rubén A.
AU - Reyes-Martínez, Reyna
AU - Roberto Pioquinto-Mendoza, J.
AU - Morales-Morales, David
N1 - Funding Information:
We would like to thank Chem. Eng. Luis Velasco Ibarra, Dr. Francisco Javier Pérez Flores, Q. Eréndira García Ríos, M.Sc. Lucia del Carmen Márquez Alonso, M.Sc. Lucero Ríos Ruiz, M.Sc. Alejandra Nuñez Pineda (CCIQS), Q. María de la Paz Orta Pérez and Q. Roció Patiño-Maya for technical assistance. The financial support of this research by CONACYT (Grant No.· CB2010-154732 ) and PAPIIT (Grants No. IN201711-3 and IN213214-3 ) is gratefully acknowledged. JRPM would like to thank CONACYT for a postdoctoral scholarship (postdoctoral agreement No. 290807-UNAM). Finally we would like to thank the facilities provided by the Departamento de Microbiologia of the ENCB-IPN for the running of the biological assays.
PY - 2015/4/5
Y1 - 2015/4/5
N2 - A series of fluorinated imines of the type [C6H4-1-(OH)-3-(CHNArF)]; ArFC6H4-4-F (1), C6H3-2,3-F2 (2), C6H3-3,5-F2 (3), C6H2-2,4,6-F3 (4), C6H4-3-CF3 (5), C6H3-3,5-(CF3)2 (6), were synthesized and fully characterized including single crystal X-ray diffraction analyses of compounds [C6H4-1-(OH)-3-(CHNC6H4-4-F)] (1), [C6H4-1-(OH)-3-(CHNC6H3-3,5-F2)] (3), [C6H4-1-(OH)-3-(CHNC6H4-3-CF3)] (5). Further analyses of these results allowed the identification of the predominant non-covalent interactions and supramolecular arrangements in the solid state. Exploration of the anti-bacterial activity against both gram-positive and gram-negative bacteria showed those compounds including F or CF3 substituents at the meta positions i.e. [C6H4-1-(OH)-3-(CHNC6H3-3,5-F2)] (3), [C6H4-1-(OH)-3-(CHNC6H4-3-CF3)] (5), [C6H4-1-(OH)-3-(CHNC6H3-3,5-(CF3)2)] (6), to be the best when their activity is compared versus ampicillin.
AB - A series of fluorinated imines of the type [C6H4-1-(OH)-3-(CHNArF)]; ArFC6H4-4-F (1), C6H3-2,3-F2 (2), C6H3-3,5-F2 (3), C6H2-2,4,6-F3 (4), C6H4-3-CF3 (5), C6H3-3,5-(CF3)2 (6), were synthesized and fully characterized including single crystal X-ray diffraction analyses of compounds [C6H4-1-(OH)-3-(CHNC6H4-4-F)] (1), [C6H4-1-(OH)-3-(CHNC6H3-3,5-F2)] (3), [C6H4-1-(OH)-3-(CHNC6H4-3-CF3)] (5). Further analyses of these results allowed the identification of the predominant non-covalent interactions and supramolecular arrangements in the solid state. Exploration of the anti-bacterial activity against both gram-positive and gram-negative bacteria showed those compounds including F or CF3 substituents at the meta positions i.e. [C6H4-1-(OH)-3-(CHNC6H3-3,5-F2)] (3), [C6H4-1-(OH)-3-(CHNC6H4-3-CF3)] (5), [C6H4-1-(OH)-3-(CHNC6H3-3,5-(CF3)2)] (6), to be the best when their activity is compared versus ampicillin.
KW - Anti-bacterial activity
KW - Crystal structures
KW - Fluorinated
KW - Non-covalent interactions
KW - Schiff bases
KW - Supramolecular arrangements
UR - http://www.scopus.com/inward/record.url?scp=84921671395&partnerID=8YFLogxK
U2 - 10.1016/j.molstruc.2014.12.080
DO - 10.1016/j.molstruc.2014.12.080
M3 - Artículo
AN - SCOPUS:84921671395
SN - 0022-2860
VL - 1085
SP - 249
EP - 257
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
ER -