Abstract
Purpose: To study the antibacterial activity of various sulfonamides derived from 1,3-benzodioxol-5- carbohydrazide.Methods: The synthesis involved the conversion of 1,3-benzodioxol-5-carboxylic acid (1) to ethyl 1,3- benzodioxol-5-carboxylate (2) and then to 1,3-benzodioxol-5-carbohydrazide (3). The target molecules, 2-(1,3-benzodioxol-5-ylcarbonyl)arylsulfonohydrazide derivatives (5a-l) were synthesized through a benignant method from aqueous medium by the reaction of 3 and arylsulfonyl chlorides (4a-l). The structural formulae of the synthesized compounds were characterized by infra red spectroscopy (IR), proton nuclear magnetic resonance (1H-NMR) and electron impact mass spectrometry (EI-MS). The compounds were screened for in vitro antibacterial activity by determining their minimum inhibitory concentration (MIC).Results: The molecule, 5k, bearing 2-hydroxy-3,5-dichlorophenyl group exhibited the highest activity with MIC of 11.92 ± 3.40 (S. typhi), 8.37 ± 2.22 (E. coli), 9.28 ± 2.31 (P. aeroginosa), 11.76 ± 1.30 (B. subtilis) and 10.30 ± 1.63 (S. aureus) μmoles/L relative to that of ciprofloxacin with 9.42 ± 1.09, 8.02 ± 2.17, 8.11 ± 1.32, 8.88 ± 2.00 and 9.23 ± 1.87 μmoles/L respectively.Conclusion: The most potent of the synthesized compounds (5k) posesses moderate activity against all the bacterial strains, while 5g remained completely inactive.Keywords: 1,3-Benzodioxol-5-carboxylic acid, Antibacterial activity, Sulfonohydrazide, Synthesis
Highlights
Most of the biologically active compounds include sulfonamides, and they are an important class of drugs showing various activities such as antimicrobial, antitumor, anticonvulsant, anticancer, anti-inflammatory, antidiuretic, antihydrod, insulin-releasing and hypoglycemic
infra red spectroscopy (IR) spectra were computed by KBr pellet method on a Jasco-320A spectrophotometer in cm-1. 1H-NMR spectra were measured in CHCl3-d1 on Bruker spectrometer at 300/400 MHz and 13C-NMR at 100 MHz
A new series of sulfonamides was synthesized from a facile method by scheme 1
Summary
Most of the biologically active compounds include sulfonamides, and they are an important class of drugs showing various activities such as antimicrobial, antitumor, anticonvulsant, anticancer, anti-inflammatory, antidiuretic, antihydrod, insulin-releasing and hypoglycemic They act as inhibitors, e.g., histone deacetylase (HDAC), carbonic anhydrase and HIV protease [1,2,3,4,5,6,7,8]. The reaction mixture of ethyl 1,3-benzodioxol-5carboxylate (2; 0.2 mol), ethanol (150 mL, 99 %) and hydrazine hydrate (15 mL, 80 %) was refluxed in a round bottom flask for 6 h. The reaction mixture of 1,3-benzodioxol-5carboxylic acid (1; 6.0 g), ethanol (24 mL, 99 %) and concentrated H2SO4 (3.0 mL) was set to reflux in 250 mL round bottom (RB) flask for 3 h till maximum completion, confirmed by TLC. Scheme 1: Outline for synthesis of 2-(1,3-benzodioxol-5-ylcarbonyl)arylsulfonohydrazide derivatives (5a-l)
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