124420-90-2Relevant academic research and scientific papers
N-H...N(pyridyl) and N-H...O(urea) hydrogen bonding and molecular conformation of N-aryl-N′-pyridylureas
Chandran, Sreekanth K.,Nath, Naba K.,Cherukuvada, Suryanarayan,Nangia, Ashwini
experimental part, p. 99 - 107 (2010/06/17)
Analysis of N-Ar-N′-4-pyridylureas (Ar = 4-X-phenyl, 4-py) crystal structures shows a gradual transition from urea...pyridyl N-H...N hydrogen bond in bifurcated synthon of R21 (6) graph set (X = H, Me, Cl) to single N-H...O and N-H...N hydrogen bonds in X = Br, I to urea N-H...O tape synthon (R21 (6) graph set) in N-phenyl-N′-tetrafluoropyridylurea. Thus the two extremes of urea pyridyl N-H...N synthon in N,N′-di(4-pyridyl) urea, N-H...O tape characteristic of diphenyl urea together with an in-between state are now visualized as snap shots in the solid-state. Most remarkably, molecular conformations too show a transition: the diaryl urea molecule is in the twisted metastable conformation in N-H...O tape structures, it is coplanar in the flat stable conformation for N-H...N structures, and one NH is in-plane while the other is oriented slightly outwards in the intermediate N-H...O and N-H...N hydrogen-bonded structure of N-4-Br-phenyl-N′-4-pyridylurea. Subtle and yet observable one-to-one molecular conformation to crystal structure systematic effects are analyzed. A one-dimensional zigzag chain in the crystal structure of N,N′-di(4-pyridyl) urea is consistent with the hydrogen bonding model for organic gelators.
N-phenyl-N'-pyridinylureas as anticonvulsant agents
Pavia,Lobbestael,Taylor,Hershenson,Miskell
, p. 854 - 861 (2007/10/02)
A series of N-phenyl-N'-pyridinylureas was examined for anticonvulsant activity. Extensive structure/activity investigations revealed optimal activity in the N-(2,6-disubstituted-phenyl)-N'-(4-pyridinyl)urea series, with 37 exhibiting the best overall anticonvulsant profile. Compound 37 was effective against seizures induced by maximal electroshock but did not protect mice from clonic seizures produced by the convulsant pentylenetetrazol. The overall pharmacological profile suggests that 37 would be of therapeutic use in the treatment of generalized tonic-clonic and partial seizures. Compound 37 was selected for Phase 1 clinical trials.
