Ecofriendly Synthesis in Aqueous Medium: An Expeditious Approach to New N,N-Diethyl Amide Bearing Benzenemethanesulfonamides

An highly expeditious synthetic approach for the synthesis of benzenemethanesulfonamides (1a-k) and their new corresponding N,N-diethyl substituted amido moieties (2a-k) has been achieved in aqueous medium at room tem-perature. The reaction condition was thoroughly optimized thereby allowing significant rate enhancement and resulting into excellent yields. The chemical structures of the successful candidates were confirmed using elemental analytical and spectroscopic data such as IR, 1H NMR, 13C NMR and some selected mass spectral dat

Synthesis and Antibacterial Activity of N,N-Diethyl-3-substituted-2-(4-methyl-phenylsulfonamido)alkanamides and their Arylsulfonamide Precursors

A series of N,N-diethyl-3-substituted-2-(4-methylphenylsulfon amido)alkanamides (8a-k) and their arylsulfonamide precursors (7a-k) have been synthesized via facile approach. The chemical structures of the synthesized compounds were confirmed by analytical data and spectroscopic means. The in vitro antibacterial screening of these compounds along with streptomycin, showed N,N-diethyl-2-(4-methylphenylsulfonamido) -3-phenylpropanamide (8j) to be the most active agent on Escherichia coli at MIC of 12.5 μg/mL and on Staphylococcus aureus at MIC of 25 μg/mL

Synthesis and Antibacterial Activity of N,N-Diethylamide Bearing Benzenesulfonamide Derivatives

Sulfonamides are known to represent a class of medicinally important compounds which are extensively used as antibacterial agents. Hence, a series of new N,N-diethyl amide bearing sulfonamides (2a-k) were synthesized via amidation of easily prepared benzenesulfonamide precursors (1a-k). The chemical structures of all synthesized compounds were substantiated using spectroscopic means such as IR, Mass spectra and 1H-NMR as well as analytical data. The antimicrobial activity of these compounds along with streptomycin, was investigated on Escherichia coli and Staphylococcus aureus. The results showed that this skeletal framework exhibited marked potency as antibacterial agents. The most active antibacterial agent against both targeted organisms was N,Ndiethyl-1-(phenylsulfonyl) piperidine-2-carboxamide (2b)

Room Temperature Synthesis and Antibacterial Activity of New Sulfonamides Containing N,N -Diethyl-Substituted AmidoMoieties

Sulfonamide drugs which have brought about an antibiotic revolution in medicine are associated with a wide range of biological activities. We have synthesized a series of α-tolylsulfonamide, 1–11 and their substituted N,N-diethyl-2-(phenylmethylsulfonamido) alkanamide derivatives, 12–22 in improved and excellent yields in aqueous medium at room temperature through highly economical synthetic routes. The chemical structures of the synthesized compounds 1–22 were confirmed by analytical and spectral data such as IR, 1H- and 13C-NMR, andmass spectra. The in vitro antibacterial activity of these compounds along with standard clinical reference, streptomycin, was investigated on two key targeted organisms. It was observed that 1-(benzylsulfonyl) pyrrolidine-2-carboxylic acid, 2 emerged as the most active compound against Staphylococcus aureus at MIC value of 1.8 μg/mL while 4-(3-(diethylamino)-3-oxo-2-(phenylmethyl sulfonamido) propyl)phenyl phenylmethanesulfonate, 22 was the most active sulfonamide scaffold on Escherichia coli at MIC value of 12.5 μg/mL

Comparative Study of the Antibacterial Activity of N, N-Diethylamido Substituted p-Toluenesulfonamides to their α-Toluenesulfonamide Counterparts

Reaction of p-toluenesulfonyl chloride with amino acids gave sulfonamides p-T1a-k which upon amidation afforded p-T2a-k. Similarly, treatment involving α-toluenesulfonyl chloride and amino acids afforded the sulfonamides α-T1a-k. These two classes of sulfonamides were synthetically modified at their COOH end position to achieve N,N-diethylamido substituted p-toluenesulfonamides p-T2a-k and α-toluenesulfonamides α-T2a-k, respectively. The chemical structures of the compounds were validated with IR, Mass spectra, NMR as well as elemental analytical data. Both classes of compounds were screened against Escherichia coli and Staphylococcus aureus and their activity were compared. It was remarkable to note that the α-toluene sulfonamides α-T2a-k were more active than their p-toluenesulfonamide counterparts p-T2a-k. Compound 1-(benzylsulfonyl)-N,Ndiethylpyrrolidine- 2-carboxamide α-T2a was the most potent antibacterial compound on S. aureus with MIC value of 3.12 μg mLG1 while N,N-Diethyl-3- phenyl-2-(phenylmethylsulfonamide) propanamide α-T2j emerged as the best antibacterial motif against E. coli with MIC value of 12.5 μg mLG1. Hence, these compounds especially the α-toluenesulfonamide core structural templates are good candidates for further study for future drug discovery

Comparative Study of the Antibacterial Activity of N, N-Diethylamido Substituted p-Toluenesulfonamides to their α-Toluenesulfonamide Counterparts

Reaction of p-toluenesulfonyl chloride with amino acids gave sulfonamides p-T1a-k which upon amidation afforded p-T2a-k. Similarly, treatment involving α-toluenesulfonyl chloride and amino acids afforded the sulfonamides α-T1a-k. These two classes of sulfonamides were synthetically modified at their COOH end position to achieve N,N-diethylamido substituted p-toluenesulfonamides p-T2a-k and α-toluenesulfonamides α-T2a-k, respectively. The chemical structures of the compounds were validated with IR, Mass spectra, NMR as well as elemental analytical data. Both classes of compounds were screened against Escherichia coli and Staphylococcus aureus and their activity were compared. It was remarkable to note that the α-toluene sulfonamides α-T2a-k were more active than their p-toluenesulfonamide counterparts p-T2a-k. Compound 1-(benzylsulfonyl)-N,Ndiethylpyrrolidine-2-carboxamide α-T2a was the most potent antibacterial compound on S. aureus with MIC value of 3.12 μg mLG1 while N,N-Diethyl-3- phenyl-2-(phenylmethylsulfonamide) propanamide α-T2j emerged as the best antibacterial motif against E. coli with MIC value of 12.5 μg mLG1. Hence, these compounds especially the α-toluenesulfonamide core structural templates are good candidates for further study for future drug discovery

Investigation of the anti-inflammatory and antinociceptive activities of Hymenocardia acida Tul. (Hymenocardiaceae)

Hymenocardia acida Tul. (Hymenocardiaceae) locally called Orupa, is traditionally used for the treatment of inflammation, including arthritis, rheumatic pain and toothache. The potential antiinflammatory and antinociceptive activities of the aqueous leaf extract of this plant were evaluated in animal models. The extract (50, 100 and 200 mg/kg) significantly (P < 0.05) and dose - dependently inhibited carrageenan and egg albumin-induced rat paw oedema development compared with control group. At 3 h of post-carrageenan administration, the highest dose of the extract (200 mg/kg, p.o) inhibited oedema formation by 66.67%. The reference drug used, indomethacin (10 mg/kg, p.o), gave an inhibition of 72.22%. The inhibitory activity shown by the aqueous leaf extract of H. acida over a period of 6 h in the carrageenan and 3 h in the egg albumin-induced paw inflammation models was comparable to that exhibited by the reference drugs used, indomethacin and cyproheptadine (10 mg/kg, p.o). The extract elicited a significant analgesic activity in the tail immersion test as evidenced by the increase in latency time in seconds as compared with the control at the end of 20 min. In the acetic acid-induced writhing model, the extract showed a dose-dependent reduction in the number of writhes at 50, 100 and 200 mg/kg when compared to the control group. The 200 mg/kg dose produced a complete protective effect, as no abdominal constriction was observed. The results obtained in this study provide some justification for the folkloric uses of H. acida as a remedy for relieving pain and  inflammation.Key words: Anti-inflammatory activity, antinociceptive activity, carrageenan, egg-albumin, Hymenocardia acida

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Abstract: An highly expeditious synthetic approach for the synthesis of benzenemethanesulfonamides (1a-k) and their new corresponding N,N-diethyl substituted amido moieties (2a-k) has been achieved in aqueous medium at room temperature. The reaction condition was thoroughly optimized thereby allowing significant rate enhancement and resulting into excellent yields. The chemical structures of the successful candidates were confirmed using elemental analytical and spectroscopic data such as IR, 1 H NMR, 13 C NMR and some selected mass spectral data. Graphical Abstract Environmental friendly synthesis of new N,N-diethyl-substituted-2-(phenylmethylsulfo namido)alkanamide derivatives was achieved in aqueous medium via synthetic modification of the benzenemethanesulfonamide precursors