Synthesis, crystal structure and biological evaluation of novel 2-(5-(hydroxymethyl)-3-phenyl-1H-pyrazol-1-yl)-1-phenylethanol derivatives

A series of novel 2-(5-(hydroxymethyl)-3-phenyl-1H-pyrazol-1-yl)-1-phenylethanol derivatives (4) was synthesized from ethyl 1-(2-oxo-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylate derivatives (3) and characterized by means of IR, H-1 NMR, HRMS and X-ray crystal diffraction. Structures of 4a, 4d, 4e and 4f were also determined by C-13 NMR. Isomeric intermediates, 3a and 5a, were unambiguously confirmed by X-ray crystal structure analysis and successfully differentiated with H-1 NMR chemical shifts of methylene bonded to pyrazole ring. Preliminary biological evaluation showed that compounds 4d and 4e could suppress A549 lung cancer cell growth through cell cycle arrest and autophagy. (C) 2010 Elsevier Masson SAS. All rights reserved.