Microwave-assisted synthesis and evaluation of naphthalimides derivatives as free radical scavengers

Abstract

A facile and efficient microwave-assisted reaction of 1,8-naphthalic anhydride derivatives with primary amines, leading to the synthesis of 1,8-naphthalimides, has been developed. Subsequently, the free radical scavenging properties of the 1,8-naphthalimide derivatives were evaluated against 2,2-diphenyl-1-picrylhydrazyl (DPPH • ). The results showed that the scavenging activities of compounds 2a, NBNA, 3b, and 3c were more efficient than that of the common synthetic antioxidant 2,6-diterbutyl-4-methylphenol (BHT), with IC 50 values of 61.9, 54.0, 42.2, and 43.1 lM, respectively. The imide groups introduced at position 4 as well as the nitro functionality at position 3 of the naphthalene moiety were the major contributors to the free radical scavenging activities.

Fluorescent Imprinted Nanoparticles for the Effective Monitoring of Irinotecan in Human Plasma

“…These very fluorescent molecules have been also used as probes for the detection of acidic drugs, biomolecules [ 30 ], and anions [ 31 ]. We have identified a small set of naphtalimide monomers ( 2 – 6 ) and synthesised them by literature methods [ 32 , 33 , 34 , 35 ]. They all contain the same N-allyl polymerisable group, and different chains substituted in the aniline ring, potentially capable to interact with irinotecan in different ways.…”

Synthesis, Characterization, Crystal Structure and Free Radical Scavenging Activities of 2-(2-Benzylamine)-6-[(2-benzylamine)amino]-5-nitro-1H-benzo[de]-isoquinoline-1,3(2H)-dione

“…1. 4-Bromo-1,8-naphthalic anhydride was treated with the mixture of potassium nitrate and sulphuric acid to offer 3-nitro-4-bromo-1,8-naphthalic anhydride in good yield 10 . The mixture of benzylamine (2.2 mmol), dimethylfomamide (DMF, 10 mL) and 4-bromo-3nitro-1,8-naphthalic anhydride (1 mmol) was refluxed at 100 ºC for 6 h. Once cooled to room temperature, red crystals of BBNID were obtained in 88 % yields.…”

Synthesis, Characterization, Crystal Structure and Free Radical Scavenging Activities of 2-(2-Butylamine)-6-[(2-butylamine)amino]-5-nitro-1H-benzo[de]-isoquinoline-1,3(2H)-dione

“…The importance of free radicals and reactive oxygen species in the pathogenesis of multifarious diseases [3][4][5] has prompted chemists to the synthesis for screening for efficient new free radical scavenging agents. Continuing our research program on the synthesis of radical scavenger effective [6][7][8] , naphthalimide skeleton is chosen in the present work as active structural core and butyl and nitro groups are introduced to explore its radical scavenging activity. The present study was to synthesize and characterize a naphthalimide derivative (2) and to evaluate the free radical activity.…”

“…1. 4-bromo-1,8-naphthalic anhydride (BNA) was treated with the mixture of potassium nitrate and sulphuric acid to offer 3-nitro-4-bromo-1,8-naphthalic anhydride in good yield, according to the literature 6 . The mixture of butylamine (2.1 mmol), dimethylfomamide (DMF, 10 mL) and 4-bromo-3nitro-1,8-naphthalic anhydride (1 mmol) was refluxed at 100 ºC for 7 h. Once cooled to room temperature, red crystals of compound 2 were obtained in 82 % yields.…”