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

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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

Polyphenolic constituents, antioxidant and hypoglycaemic potential of leaf extracts of Acalypha godseffiana from Eastern Nigeria: In vitro study

Background: Acalypha godseffiana is an important plant used as an ornamental and herbs; its leaves are used in the management of diseases like diabetes in Eastern Nigeria. Aim: The study aims at linking the hypoglycemic activity extracts of leaves of A. godseffiana to their polyphenolic contents. Setting: Fresh leaves of A. godseffiana were obtainedfrom Imo State, Nigeria, identified in University of Lagos Herbarium, air-dried, pulverized and kept for investigations. Method: The phytochemical compositions and antioxidant potentials of acetone, aqueous, ethanol and methanol extracts of A. godseffiana were determined using adopted methods. An in-vitroapproach was used to evaluate the hypoglycemic potentials of the extracts on α-amylase and α-glucosidase enzymes. The mechanism of inhibitions was studied using the Lineweaver-Burk plot. Results: Antioxidant results revealed that total antioxidant capacity of the acetone extract (IC50: 0.34 mg/mL) showed better activity compared to the standards (silymarin 0.52 mg/mL; gallic acid 0.51 mg/mL). Thehypoglycemic findings confirmed that acetone extract demonstrated strong and mild inhibitory potential against α-amylase and α-glucosidase respectively, showing concentration dependent with IC50 values of 2.33 mg/mL and 0.13 mg/mL. The observed hypoglycemic and antioxidant potentials of acetone extract of A. godseffiana correlate to its high polyphenolic contents which include phenols (133.20 mg gallic acid g-1), flavonoid (350.60 mg quercetin g-1) and tannins (264.67 mg catechin g-1). The mechanisms of action exhibited by the acetone extractwere uncompetitive and mixed non-competitive which can be attributed to its inhibitory properties on α-glucosidase and α-amylase respectively. Conclusion: The results obtained from this study validate the acetone leaves extract of A. godseffiana as potential agent in management of sugar related disorder

<i>N</i>-Aryl Amino Acids as Potential Antibacterial Agents

The resistance of bacteria to current antibiotic drugs and the re-occurrence of different ailments after several therapeutic protocols continue to be a cause for concern. Arylated amino acids are vital synthons to many compounds; they serve as essential building blocks in the synthesis of nitrogen heterocycles with various biological activities. This research reports on the synthesis of some N-aryl amino acids and evaluates their antibacterial activities. The N-aryl amino acids 3a–3j were obtained by reacting different 4-substituted fluorobenzene 1a–1d with different amino acids 2a–2g via a metal-free base-induced aryl amination reaction of aryl halides. The antibacterial activities of the synthesized compounds were evaluated against eight bacterial strains (Four Gram-positive, Bacillus subtilis (ATCC 6633), Streptococcus pneumonia (ATCC 33400), Staphylococcus aureus (ATCC 25923), and Staphylococcus epidermidis (ATCC 14990), and four Gram-negative, Enterobacter cloacae (ATCC 43560), Escherichia coli (ATCC 25922), Proteus mirabilis (ATCC 43071), and Klebsiella oxytoca (ATCC 13182) using the agar well diffusion method with streptomycin as a reference drug. The biological screening indicates that the synthesized compounds 3a, 3e, and 3j have promising broad-spectrum antibacterial potential, as the N-aryl amino acid displayed activity that was comparable to the standard drug against Streptococcus pneumonia, Escherichia coli, and Proteus mirabilis

Antibacterial potentials and DNA study of cobalt(II) complexes containing aminophenol Schiff base moiety

The present study was carried out to investigate the effect of substituent groups on the antibacterial activities of 2-aminophenol Schiff bases and their cobalt (II) complexes. Development of new compounds with potential effects against pathogenic organisms has become necessary due to the increase in microbial resistance reported for existing antiseptics and disinfectants. In line with this, new cobalt (II) complexes with Schiff bases derived from 2-aminophenol and p-substituted benzaldehydes were synthesized. The compounds were characterized using elemental analysis, mass spectrometry, atomic absorption spectroscopy, electrospray ionization mass spectrometry, infrared spectroscopy, 1H NMR and electronic absorption spectroscopy. Results indicate that all metal complexes had a 1:2 metal ligand ratio with magnetic moments characteristic of tetrahedral geometry around the metal ion. The Schiff bases and their metal complexes were screened for in-vitro antibacterial activities against 6 human pathogenic bacteria usually found around the hospitals and homes; Escherichia coli (ATCC 8739), Staphylococcus aureus (ATCC 6538), Pseudomonas aeruginosa (ATCC 19582), Bacillus cereus (10702), Enterococcus faecalis (ATCC 29212) and Kribsella pneumonia (ATCC 10031) with ampicillin used as the reference compound. DNA binding study using calf thymus DNA revealed intercalative mode of activity. The result showed that Schiff bases exhibited moderate inhibitory activity against the tested microorganisms while Schiff base metal complexes exhibited higher antibacterial activity when compared to ampicillin. Our results indicate that these complexes can be employed as active ingredients in development of broad-spectrum antibacterial agents

Drug design and in-silico study of 2-alkoxylatedquinoline-3-carbaldehyde compounds: Inhibitors of Mycobacterium tuberculosis

Tuberculosis (TB) caused by Mycobacterium tuberculosis (MTB) is a deadly communicable disease that frequently affects the lungs. Current treatment protocols are bedeviled by extensive drug-resistant (XDR) and the evolution of multidrug-resistant (MDR-TB) strains. Virtual in-silico drug discovery tools were used to investigate thirty-two hypothetical 2-alkoxylatedquinoline-3-carbaldehyde compounds for screening against ten different diseases proteins based on drug-likeness, oral bioavailability, pharmacokinetics, global chemical reactivity and their theoretical binding affinities. Their chemical structures were optimized at the density functional theory (DFT) using Becke's three-parameter exchange functional with Lee–Yang–Parr correlation function (B3LYP) and the triple zeta basis set 6–311 in a vacuum using Gaussian 09 W software. Docking study using Pyrx and Discovery studio. Fourteen compounds; 4 - 6, 12 – 14, 19 – 22 and 27–30 complied with the established drug-likeness rules, however, five compounds 12, 13, 27, 28 and 29 exhibited no significant toxicity. Structural activity relationship revealed that shorter (n  5) alkyloxyl substituents at position-2 of the quinoline moiety reduces drug-likeness and increases toxicity. Individually, the binding energies obtained were (-8.9 kcal/ mole) against malaria for compound 12 and (-8.2 kcal/mole) against the diabetes for compound 29, both highest for the ten diseases investigated. Mycobacterium Tuberculosis proteins investigated. Molecular dynamics also confirms that 12 and 27 binds very well in the active pocket of Mycobacterium tuberculosis and calculated total free binding energy from MMPBSA is -97.53 ± 2.47 and -58.62 ± 2.94 kJ/mol respectively. The five lead compounds all had binding energies higher than the reference tuberculosis drugs; Isoniazid and Ethambutanol