Crystal structure and electronic properties of two nimesulide derivatives: A combined X-ray powder diffraction and quantum mechanical study

Three Nimesulide Derivatives: Synthesis, Ab Initio Structure Determination from Powder X-ray Diffraction, and Quantitative Analysis of Molecular Surface Electrostatic Potential

“…When the nitro group in 1 is replaced by a strong electron donating amino (NH 2 ) group in OPEKOK, the N atom acts as a double donor to two sulfonyl O atoms to produce two C 2 2 (18) chains which combine together into a 2D supramolecular assembly built with fused R 2 2 (12) and R 2 2 (36) rings. The replacement of NO 2 group in 1 by bulky cyclic substituents, such as dioxopyrrolidin-1-yl in 2 , dioxopyrrol-1-yl in MUTJUH, dioxoisoindole-2-yl in OPEKUQ, phenyl-1 H -triazol-1-yl in QOJSAL, tolyl-1H-triazol-1-yl in QOJSEP, and chloromethyl phenoxymethyl-1 H -triazol-1-yl in QOJSIT, leads to different hydrogen bonding patterns. The molecular assembly in these compounds exhibits cyclic R 2 2 (8) ring generated by N­(sulfonamide)-H···O­(sulfonyl) hydrogen bonds.…”

“…In nimesulide polymorphs ( 1a and 1b ) with a strong electron withdrawing nitro (NO 2 ) group at the trans position with respect to the methanesulfonamide moiety, the N­(sulfonamide)–H···O­(sulfonyl) hydrogen bond generates one-dimensional molecular tapes comprising of C 2 2 (16) synthon. When the nitro group in 1 is replaced by a strong electron donating amino (NH 2 ) group in OPEKOK, the N atom acts as a double donor to two sulfonyl O atoms to produce two C 2 2 (18) chains which combine together into a 2D supramolecular assembly built with fused R 2 2 (12) and R 2 2 (36) rings. The replacement of NO 2 group in 1 by bulky cyclic substituents, such as dioxopyrrolidin-1-yl in 2 , dioxopyrrol-1-yl in MUTJUH, dioxoisoindole-2-yl in OPEKUQ, phenyl-1 H -triazol-1-yl in QOJSAL, tolyl-1H-triazol-1-yl in QOJSEP, and chloromethyl phenoxymethyl-1 H -triazol-1-yl in QOJSIT, leads to different hydrogen bonding patterns.…”

“…Nimesulide, N -(4-nitro-2-phenoxyphenyl) methanesulfonamide ( 1 ), is a well-known nonsteroidal anti-inflammatory drug (NSAID), which can inhibit cyclooxygenase-2 (COX-2) enzyme selectively . Since the nitro group in 1 is known to be associated with toxic side effects including gastrointestinal erosions, − several nimesulide derivatives aimed at improving its tolerability profile and reducing its toxicity have been reported by changing in 1 the nitro group with an appropriate electron withdrawing moiety. − With this background, we synthesized three nimesulide derivatives, N -[4-(2,5-dioxo-pyrrolidin-1-yl)-2-phenoxyphenyl] methanesulfonamide ( 2 ), N -[4-(4-methanesulfonylamino-3-phenoxy phenylsulfamoyl) phenyl] acetamide ( 3 ), and 4-(4-methanesulfonylamino-3-phenoxyphenyl-carbamoyl)-butanoic acid ( 4 ), with different aromatic/aliphatic substitutions replacing the nitro group in nimesulide ( 1 ) to analyze differences in crystal packing due to changes in the substituents. Since our attempts to grow suitable single crystals of 2 – 4 for X-ray analysis resulted in assemblies of microcrystals, structure determination was attempted from X-ray powder diffraction.…”

Nimesulide Based Novel Glycolamide Esters: Their Design, Synthesis, and Pharmacological Evaluation

“…The design of our target molecules A was based on the structural modifications of nimesulide [14][15][16][17][18][19][20]. We anticipated that combining the structural features of nimesulide and glycolamide esters in a single molecule may afford novel template for the design and synthesis of new anticancer agents.…”

N-(2-Phenoxy-4-(3-phenoxyprop-1-ynyl)phenyl)methane Sulfonamide

“…Nimesulide B (Figure 1), a sulfonamide based well known antiinflamatory agent, is presently in patient's use in certain countries. Because of their common cytotoxic properties and our interest in nimesulide (N-(4nitro-2-phenoxy phenyl)methane sulfonamide) derivatives [3][4][5][6][7][8][9][10] as potential cytotoxic agents, we designed the appropriately functionalized hybrid molecule C containing structural features of both A and B (Figure 1). The alkynylation of iodoarenes via C-C bond forming reaction under Pd-Cu catalysis (the Sonogashira coupling) [11] has found wide applications in organic synthesis [12].…”