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

The Effect of Drying Methods on the Chemical Composition of the Essential Oil of Caesalpinia Pulcherrima Growing in Lagos, Nigeria

This research studied the effects of different drying methods on the yield and chemical composition of hydrodistilled essential oil from the red variety of leaves of Caesalpinia pulcherrima. A total of 26, 23, 30 and 25 compounds were identified in the oils of the fresh, air-dried, sun-dried and oven-dried plant materials, respectively. In general, the air-dried plant yielded more essential oils than the fresh, sun-dried and oven-dried plant. The air-dried, sun-dried and oven-dried plant materials yielded 0.90 %, 0.20 % and 0.58 % of the essential oils, respectively whereas the fresh plant materials yielded oils of 0.63 %. The essential oils of Caesalpinia pulcherrima were composed mainly of sesquiterpenoids. The fresh leaf oil comprises caryophyllene, 15.51 %; α -cadinol 14.36 %; γ–muurolene, 13.28 %; nerolidol 8.32 % as the most prominent components. While, the major components common to the different drying methods are air-dried; (phytol, 12.28%; copaene, 9.07 %; γ-pyronene, 8.95 %; neryl propanoate, 6.55 %), sun-dried (neryl propanoate, 8.18 %; copaene, 5.49 %; phytol, 4.72 %; γ -pyronene, 0.87 %), oven-dried (copaene, 18.77 %; neryl propanoate, 7.61 %; γ-pyronene, 4.59 %; phytol - 3.25 %). This results showed that similar major compounds were present in all the dried leaf oils but at varying quantities, whereas, they all differ from the major compounds of the fresh leaf oil. This disparity may be due to chemical transformation of the components in the different environ ments exposed to for moisture removal

In Vitro Antimalarial, Antimicrobial and Trypanocidal Potentials of the Leaf Extract and Fractions of Bridelia ferruginea (Benth.)

Bridelia ferruginea Benth. (Euphorbiaceae) is a plant used for various medicinal purposes including the treatment of protozoan infections in many African countries. The present study was aimed to evaluate the in vitro antimalarial, antimicrobial and antitrypanasomal activity of the methanol crude extract and fractions of the medicinal plant, Bridelia ferruginea. Crude extract from dried leaves of Bridelia ferruginea was prepared by cold maceration and fractionated using a reverse phase column under reduced pressure with water – methanol mixtures. The extracts and fractions were tested to determine their biological activities. In vitro antimalarial activity was determined by the plasmodial lactate dehydrogenase culture sensitivity assay while antitrypanosomal activity was tested in vitro against a culture of Trypanosoma brucei promastigotes. The crude extract of B. ferruginea exhibited significant antitrypanasomal activity with an IC50 of 8.48 µg/mL which was further enhanced in some of the fractions like the MeOH fraction (BFD) with an IC50 of 1.04 µg/Ml which indicates very good activity. Sub – fraction BFF (obtained from 1:3 H2O:MeOH fraction – BFC) exhibited the best antimalarial activity among all the fractions and sub – fractions with an IC50 value of 19.73 µg/mL against P. falciparum D6 and 20.49 µg/mL against P. falciparum W2. There was no observable antibacterial or antifungal activity for all crude extracts, fractions and sub – fractions. The results from this study have validated the leaves of Bridelia ferruginea as potential sources of antimalarial and antitrypanosomal agents which can serve as a lead in drug development

SYNTHESIS AND SOLVATOCHROMIC BEHAVIOUR OF SOME HETEROCYCLYIC ISONICOTINOHYDRAZIDE SCHIFF BASES

The solvatochromic behaviour of three heterocyclic Schiff bases derived from isonicotinic acid hydrazide (INH) and pyrrole-2-carboxaldehyde (L1), furan-2-carboxaldehyde (L2) and thiophene-2-carboxaldehyde (L3) was studied in nine solvents of different polarities.  The electronic transition properties were investigated using the Kamlet-Taft parameters, dielectric function, refractive index function and Catalan parameters.   The results indicate that the hydrogen bond acceptor properties of the solvent are more effective in directing the solvatochromic behavior of the Schiff bases.

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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

Sustainable generation of bioethanol from sugarcane wastes by Streptomyces coelicolor strain COB KF977550 isolated from a tropical estuary

The damaging effect and challenges associated with the use of fossil fuel is enormous and very costly. Biofuels could be obtained from plant biomass wastes which are known to be sources of environmental pollution and breeding grounds for vectors of diseases. Sugarcane bagasse was exploited as a renewable substrate for obtaining bioethanol using Streptomyces strain COB KF977550 as inoculum. Submerged aerobic batch fermentation was performed in flasks containing mineral salts medium supplemented with 5.0 g (w/v) sugarcane bagasse. Incubation was done in a shaker (150 rpm) at 30 oC for 21 days. Microbial growth was assessed by measurement of the optical density (O.D 600nm) at 3-day intervals. Fractional distillation was carried out in batch mode using a simple fractional distillation setup. Metabolic products were determined using GC-FID. Further analyses were performed using FTIR and GC-MS. The optical density of S.coelicolor strain COB KF977550 increased from 0.9 to 1.41. The GC-FID showed that 43.08 g/L ethanol was generated. Interestingly, the results showed the presence of diverse biochemicals released into the medium in addition to the main product ethanol. Ten carboxylic acids including formic acid, glycolic acid, tartaric acid, acetic acid, citric acid, oxalic acid, malic acid, lactic acid, n-valeric acid, and 3-hydroxybutyric acid were identified as biochemical organic acids by-products

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

The Effect of Drying Methods on the Chemical Composition of the Essential Oil of Caesalpinia Pulcherrima Growing in Lagos, Nigeria

This research studied the effects of different drying methods on the yield and chemical composition of hydrodistilled essential oil from the red variety of leaves of Caesalpinia pulcherrima. A total of 26, 23, 30 and 25 compounds were identified in the oils of the fresh, air-dried, sun-dried and oven-dried plant materials, respectively. In general, the air-dried plant yielded more essential oils than the fresh, sun-dried and oven-dried plant. The air-dried, sun-dried and oven-dried plant materials yielded 0.90 %, 0.20 % and 0.58 % of the essential oils, respectively whereas the fresh plant materials yielded oils of 0.63 %. The essential oils of Caesalpinia pulcherrima were composed mainly of sesquiterpenoids. The fresh leaf oil comprises caryophyllene, 15.51 %; α -cadinol 14.36 %; γ–muurolene, 13.28 %; nerolidol 8.32 % as the most prominent components. While, the major components common to the different drying methods are air-dried; (phytol, 12.28%; copaene, 9.07 %; γ-pyronene, 8.95 %; neryl propanoate, 6.55 %), sun-dried (neryl propanoate, 8.18 %; copaene, 5.49 %; phytol, 4.72 %; γ -pyronene, 0.87 %), oven-dried (copaene, 18.77 %; neryl propanoate, 7.61 %; γ-pyronene, 4.59 %; phytol - 3.25 %). This results showed that similar major compounds were present in all the dried leaf oils but at varying quantities, whereas, they all differ from the major compounds of the fresh leaf oil. This disparity may be due to chemical transformation of the components in the different environ ments exposed to for moisture removal