Synthesis of novel quinoline analogues of nimesulide: An unusual observation

Abstract

in Wiley Online Library (wileyonlinelibrary.com).Reduction of nimesulide followed by treating the N-acyl derivative of resulting arylamine with Vilsmeier-Haack reagent provided novel 2-chloro-3-formylquinoline derivatives. The construction of quinoline ring using Vilsmeier-Haack reagent afforded an unexpected compound, N-(2-chloro-3-formyl-7phenoxy quinolin-6-yl)formamide, in addition to the expected product. The structure of this unexpected quinoline derivative was established via single-crystal X-ray analysis and its formation could be explained by an unprecedented N-S bond cleavage under Vilsmeier-Haack reaction conditions. The 2chloro-3-formylquinoline derivatives obtained were converted to a number of corresponding Schiff bases with potential pharmacological importance.

Recent advances in the chemistry of 2-chloroquinoline-3-carbaldehyde and related analogs

“…Condensation of N-alkylquinolines 56 with complex of feruloyl acetone diuoroboronite in the presence of n-butylamine followed by heating in a mixture of methanol/water afforded the respective 3-(5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-3-oxohepta-1,4,6-trien-1-yl)-1,6-disubstituted-quinolin-2(1H)-ones 58 (Scheme 12). 69 On the other hand, 2-chloroquinoline-3-carbaldehyde (16a) reacted with thiomorpholine (59) by heating in ethanol containing anhydrous potassium carbonate to furnish 2thiomorpholino-quinoline-3-carbaldehyde (60). Compound 60 reacted with acetophenones 61a-j in ethanol containing anhydrous K 2 CO 3 under microwave (MW) irradiation conditions to afford the respective unsaturated ketones 62a-j, respectively (Scheme 13).…”

Nonsteroidal Anti‐inflammatory Drug‐based N‐Allylidene Benzohydrazides and 1‐Acyl‐2‐pyrazolines: Their Synthesis as Potential Cytotoxic Agents In Vitro

“…Thus, a combination of A and an appropriate NSAID in a single molecule is expected to provide a new template E (Figure ) for the design and identification of novel anticancer agents. Prompted by this idea and because of our longstanding interest in the chemical modification of NSAIDs , we became interested in the synthesis and pharmacological evaluation of a library of compounds based on E . Herein, we report in vitro cytotoxic activities of novel 1‐acyl‐2‐pyrazoline derivatives based on E incorporating the structural features of known NSAIDs, for example, mefenamic acid and ibuprofen.…”

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].…”