Synthesis , Characterization and Biological activity of new derivatives of Chromen-2-one

Abstract

I S S N 2321-807XV o l u m e 15 N u m b e r 1 J o u r n a l o f A d v a n c e s i n C h e m i s t r y 6130 AbstractWe report the organic syntheses of new derivatives from Chromen-2-one and their antibacterial activity. Compounds 3-Hydroxy-4-(2-oxo-2H-chromen-4-ylamino) -benzenesulfonyl chloride (1a), 4-[3-(acetyl-phenyl-sulfamoyl)-2-oxo-2H-chromen-4-ylamino]-3-hydroxy-benzenesulfonyl chloride 2aAll Structures have been synthesized and characterized using melting points, IR spectra, 1 H-NMR, 13 C-NMR spectra, and elemental analyses. The purified synthesized compounds (1a,2a,3a), at concentrations 2,3,5 mg/ml was tested for their antibacterial activity against three bacterial cultures; Staphylococcus aureus, Escherchia coli and Bacillus cereus. The antibacterial activity of synthesized compounds are compared with antibacterial activity of standard antibiotics cephalexine and streptomycine.The compounds (1a,2a,3a) shows different bacteriostatic and bacteriocidal activity.Keywords: Chromen-2-one derivatives streptomycine 1.IntroductionStarting from Chromen-2-one (a); are synthesized some new derivatives 1a,2a,3a (Schemes 1,2,3). Coumarine derivatives are large group of heterocyclic with oxygen as heteroatom.Coumarine is a chemical compound (specifically , a benzo-α-pyrone) found in many plants notably in high concentration in the tonka bean ( Dipteryx odorata), vanilla grass (Anthoxanthum odoratum) , woodruff (Galium odoratum) , mullein (Verbascum spp), and sweet grass (Hierochloe odorata).Coumarine and their derivatives have shown various biological activities.Other several coumarin derivatives have antimicrobial properties (Sanghyun ; et al 1996 ; Mohareb et al 2007;Nofal et al 2000), with reflux and condensation we have synthesize some new coumarine derivatives and to investigate their antibacterial activity against Staphylococcus aureus, E.coli and Bacillus cereus.The antibacterial activity of synthesized compounds is compared with antibacterial activity of Cefalexine and Streptomycine. Material and Methods 2.Experimental ChemistryCompounds 4-[Acetyl-(2-oxo-2H-chromen-4-yl)-amino]-benzenesulfonyl chloride 1a, 4-[Acetyl-(2-oxo-3-phenylsulfamoyl-2H-chromen-4-yl)-amino]-benzenesulfonyl chloride 2a,2-{4-[Acetyl-(4-chlorosulfonylphenyl)-amino]-2-oxo-3-phenylsulfamoyl-2H-chromen-7-ylamino}-benzoic acid 3a., are synthesized. MeasurementThe identification of Chromen-2-one derivatives (1a,2a,3a,), is made by using melting point, IR, 1 H-NMR, 13 C-NMR spectra and elemental analysis.Melting point was determinated on an Electrothermal apparatus (Fisher Scientific 2555) in a open capillary tube and wa not corrected. Infrared spectra were recorded in cm-1 for KBr pellts on a FT-IR Shimadzu 8400S spectrophotometer with resolution 4 cm-1 , 1 H-NMR spectra were recorded on a Bruker UNITY plus-500 'NMR 1' spectrometer using DMSO-d6 as the solvent and TMS as the internal references standard (σ = 0,00 ppm). Chemical shifts are expressed in δ ppm. Mass spectra were taken on a LKB 9000 mass spectrometer. Element analysze was performe...

Recent progress on coumarinscaffold‐basedanti‐microbial agents (PartIII)

“…The latter condensed with 2‐aminobenzoic acid in acetonitrile in the presence of Et 3 N at 45°C to achieve the coumarin derivative 189 (Scheme 41). [ 107 ] Compounds 187‐189 , which contain sulphonyl group, showed a significant antibacterial effect against; S. aureus , E. coli , and B. cereus . [ 107 ]…”

“…[ 107 ] Compounds 187‐189 , which contain sulphonyl group, showed a significant antibacterial effect against; S. aureus , E. coli , and B. cereus . [ 107 ]…”