Docking studies and the crystal structure of two tetrazole derivatives: 5-(4-chlorophenyl)-1-{4-(methylsulfonyl)phenyl}-1H-tetrazole and 4-{5-(4-methoxyphenyl)-1H-tetrazol-1-yl}benzenesulfonamide

Abstract The structures of 5-(4-chlorophenyl)-1-{4-(methylsulfonyl)phenyl}-1 H -tetrazole ( 3 ) and 4-{5-(4-methoxyphenyl)-1 H -tetrazol-1-yl}benzenesulfonamide ( 5 ) have been determined by X-ray crystallography. Tetrazoles 3 and 5 crystallize in the monoclinic space groups Ia and P 2 1 /c, respectively. The cell dimensions of azole 3 are a  = 11.0413 (5) A, b  = 11.8428 (5) A, c  = 12.2483 (5) A 3 , β  = 111.7129 (4)°, V  = 1487.95 (11) A 3 , and Z  = 4. Its structure was refined to R 1  = 0.0254 (for 3429 observed reflections [ I  ≥ 2 σ ( I )]) and wR 2  = 0.0651 (for all 3300 unique reflections). The cell dimensions of azole 5 are a  = 17.112 (3) A, b  = 6.5904 (10) A, c  = 12.935 (2) A 3 , β  = 93.1981 (19)°, V  = 1456.5 (4) A 3 , and Z  = 4. Its structure was refined to R 1  = 0.0336 (for 3010 observed reflections [ I  ≥ 2 σ ( I )]) and wR 2  = 0.0875 (for all 2463 unique reflections). The tetrazole rings are essentially planar, while the aryl rings at the 1- and 5-positions of each compound show no conjugation to the tetrazole groups. Compound 5 exhibits a network of intermolecular hydrogen bonds generated by interactions between adjacent sulfonamide groups. The molecular docking studies were carried out to understand the orientation and the interaction of each molecule inside the active site of the cyclooxygenase-2 enzyme, followed by comparison with the bioassay studies as COX-2 inhibitors.