caa a22 4500 463184157 CHVBK 20180406164847.0 cr unu---uuuuu 170326e20070901xx s 000 0 eng 10.1007/s10870-007-9221-x doi (NATIONALLICENCE)springer-10.1007/s10870-007-9221-x X-ray Structures of Pharmacologically Active 2-(3,5-Dimethyl-pyrazol-1-yl)-methylacetanilides [Elektronische Daten] [Christina Zalaru, Mino Caira, Mircea Iovu, Elena Cristea] X-ray structures of three pharmacologically active lidocaine analogs, containing a common, substituted pyrazole moiety as the basic residue and variously substituted phenyl rings as the hydrophobic residue, have been determined. This isomeric series comprises 2-(3,5-dimethyl-pyrazol-1-yl)-2′-methylacetanilide (1), 2-(3,5-dimethyl-pyrazol-1-yl)-3′-methylacetanilide monohydrate (2), and 2-(3,5-dimethyl-pyrazol-1-yl)-4′-methylacetanilide (3). Crystal data are 1: space group P2 1 /c with a=4.7617(2), b=11.5638(4), c=23.603(1)Å, β=90.736(2)°, Z=4; 2: P2 1 /c with a=4.7260(1), b=13.7001(4), c=21.7006(6)Å, β=93.425(1)°, Z=4; 3: P2 1 /n with a=6.4103(3), b=24.584(1), c=8.4449(4)Å, β=100.273(3)°, Z=4. In 1-3, the amide bond is trans-planar but the basic and hydrophobic residues adopt different orientations relative to this plane. Hydrogen bonding in 1 and 3 is based on C(4) linear arrays whereas in the monohydrate 2, the presence of water gives rise to R 4 4 (16) ring motifs. A summary of the local anesthetic and anti-arrhythmic properties of 1-3 is provided. Graphical abstract: X-ray Structures of Pharmacologically Active 2-(3,5-Dimethyl-pyrazol-1-yl)-methylacetanilides Christina Zalaru, Mino R. Caira, Mircea Iovu, and Elena Cristea The title compounds are lidocaine analogs that display local anesthetic and anti-arrhythmic activities. X-ray analyses revealed a range of solid-state conformations among these isomeric compounds as well as variation in hydrogen bonding schemes, namely C(4) (R = o-, p-CH3) and R44(16) (R = m-CH3, monohydrate crystal). 1,1-Os3(CO)9(μ-CO)(phen) Springer Science+Business Media, LLC, 2007 2-(3,5-Dimethyl-pyrazol-1-yl)-methylacetanilides nationallicence Lidocaine analogs nationallicence X-ray structures nationallicence Anesthetic nationallicence Anti-arrhythmic activities nationallicence Zalaru Christina Department of Organic Chemistry, University of Bucharest, 90-92 Panduri Road, Bucharest, Romania aut Caira Mino Department of Chemistry, University of Cape Town, 7701, Rondebosch, South Africa aut Iovu Mircea Department of Organic Chemistry, University of Medicine and Pharmaceutics "Carol Davila”, 6 Traian Vuia St., Bucharest, Romania aut Cristea Elena Department of Organic Chemistry, University of Medicine and Pharmaceutics "Carol Davila”, 6 Traian Vuia St., Bucharest, Romania aut Journal of Chemical Crystallography Springer US; http://www.springer-ny.com 37/9(2007-09-01), 623-628 1074-1542 37:9<623 2007 37 10870 https://doi.org/10.1007/s10870-007-9221-x text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10870-007-9221-x text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Zalaru Christina Department of Organic Chemistry, University of Bucharest, 90-92 Panduri Road, Bucharest, Romania aut NATIONALLICENCE 700 1- Caira Mino Department of Chemistry, University of Cape Town, 7701, Rondebosch, South Africa aut NATIONALLICENCE 700 1- Iovu Mircea Department of Organic Chemistry, University of Medicine and Pharmaceutics "Carol Davila”, 6 Traian Vuia St., Bucharest, Romania aut NATIONALLICENCE 700 1- Cristea Elena Department of Organic Chemistry, University of Medicine and Pharmaceutics "Carol Davila”, 6 Traian Vuia St., Bucharest, Romania aut NATIONALLICENCE 773 0- Journal of Chemical Crystallography Springer US; http://www.springer-ny.com 37/9(2007-09-01), 623-628 1074-1542 37:9<623 2007 37 10870 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer