Synthesis and crystal structure of N-[(dimethylamino)methylidene]-4-[1-(4-nitropheny1)-1H-tetrazol-5-yl]-benzenesulfonamide: Molecular docking and bioassay studies as cyclooxygenase-2 inhibitor

The synthesis of N-[(dimethylamino)methylidene]-4-[1-(4-nitropheny1)-1H-tetrazol-5-yl]benzenesulfonamide (3) has been easily approached and the structure has been determined by X-ray crystallography. Tetrazole 3 crystallizes in the monoclinic space group C2/c, with the cell parameters determined as a = 35.5408 (18) angstrom, b = 7.6972 (4) angstrom, c = 13.0700 (7) angstrom(3), beta = 96.8598 (6)degrees, V = 3549.9 (3) angstrom(3), and Z = 8. Its structure refines to R-1 = 0.0341 (for 2986 observed reflections [I >= 2 sigma(I)]) and wR(2) = 0.0990 (for all 3637 unique reflections). The aryl rings at the 1- and 5-positions show no conjugation to the tetrazole group, and the [(Dimethylamino)methylene]aminosulfonyl (Me2NCHNSO2) group is disordered, with the two disorder conformers being related by a pseudo mirror plane. In the crystal, intermolecular interactions between adjacent molecule of 3 are dominated by weak (2.4-2.7 angstrom) CeH center dot center dot center dot O and CeH center dot center dot center dot N hydrogen bonds. The molecular docking studies were carried out to understand the interaction of compound 3 within the active site of the cydooxygenase-2 enzyme, followed by a comparison study with the celecoxib drug as a reference compound. The in vitro bioassay studies of tetrazole 3 toward cyclooxygenase-1 and cyclooxygenase-2 enzymes showed that compound 3 has no inhibition potency for either enzyme. (c) 2016 Elsevier B.V. All rights reserved.