Faculty of Applied Sciences
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Item Sulfonic acid functionalized boron nitride nano materials as a microwave-assisted efficient and highly biologically active one-pot synthesis of piperazinyl-quinolinyl fused Benzo[c]acridine derivatives(Elsevier, 2017) Murugesan, Arul; Gengan, Robert Moonsamy; Anand, KrishnanBoron nitride nano material based solid acid catalyst was found to be an efficient and reusable sulfonic acid catalyst for the synthesis of one-pot Knoevenagel and Michael type reactions in 3, 3-dimethyl-9-(2-(4-methylpiperazin-1-yl) quinolin-3-yl)-3, 4, 9, 10-tetrahydroacridin-1(2H)-one derivatives under mi-crowave irradiation conditions. The catalyst was prepared by mixing boron nitrile and (3-mercaptopropyl) trimethoxysilane. This is simple and safe method for the preparation of solid acid catalysts. The morphological properties of catalyst determined by using FT-IR, XRD, TEM, SEM and Raman spectroscopy. The synthesised catalyst was employed in Knoevenagel and Michael type reactions to synthesise novel piperazinyl-quinolinyl based acridine derivatives. Furthermore the newly-synthesised compounds have been used for molecular docking in DNA binding studies. The method developed in this study has the advantages of good yield, simplicity coupled with safety and short reaction time. Most importantly it was found that the solid acid catalyst can be recycled with only 5% loss of activity.Item Design, synthesis, anticancer, antimicrobial activities and molecular docking studies of novel quinoline bearing dihydropyridines(Elsevier, 2016) Nkosi, S'busiso Mfan'vele; Anand, Krishnan; Anandakumar, S.; Singh, Sanil; Chuturgoon, Anil A.; Gengan, Robert MoonsamyA new series of eight quinoline bearing dihydropyridine derivatives (A1–A8) were synthesized in high yield and in short reaction time by a four component reaction of 2-chloro-3-fomyl quinoline, malononitrile, arylamines and dimethyl acetylenedicarboxylate in the presence of a catalytic amount of triethylamine. The compounds were fully characterized by IR, NMR and GC–MS. These compounds were screened for potential biological activity in an A549 lung cancer cell line and were also evaluated for their antibacterial activities against Pseudomonas aeruginosa ATCC 27853, Escherichia coli ATCC 25922 and Staphylococcus aureus ATCC 29213 whilst their molecular docking properties in an enzymatic system were also determined. Compounds A2, A3, A4 and A8 showed anti-proliferative activity; with A4 having the highest toxicity at 250 μg/mL and A8 has high toxicity at 125, 250 and 500 μg/mL, respectively. Antibacterial results indicated that A4 have significant activity against tested microorganisms at the minimum inhibitory concentration (MIC) values of 32 μg/mL against Pseudomonas aeruginosa and Escherichia coli,and 16μg/mL against Staphylococcus aureus. Docking of A1 with human mdm2 indicated the lowest binding energy (−6.111 Kcal/mol) thereby showing strong affinity of the ligand molecule with the receptor which has been stabilized by strong hydrogen bond interactions in the binding pocket. This confirms that A1 is a better inhibitor for E3 ubiquitin-protein ligase mdm2.Item Influence of epoxy group in 2-pyrrolidonium ionic liquid interactions and thermo-physical properties with Ethanoic or Propanoic acid at various temperatures(ACS Publications, 2016) Vasanthakumar, Arumugam; Redhi, Gan G.; Gengan, Robert MoonsamyIn this present study, the interaction between a carboxylic acid and ionic liquids, in terms of their binary mixtures and corresponding thermo-physical properties, was investigated. Here, the novel ionic liquid (IL) [EPMpyr]+[Cl]− was synthesized, and it has been mixed with ethanoic or propanoic acids. The influence of the epoxy group in this ionic liquid was more strongly affected with the acids, and their physicochemical properties at varied temperatures are discussed in term of density (ρ), viscosity (η), speed of sound (u), and refractive index (n) measurements. The density (ρ), speed of sound (u), viscosity (η), and refractive index (n) of the IL, ethanoic acid, propanoic acid, and their corresponding binary mixtures {[([EPMpyr]+[Cl]− (1) + ethanoic or propanoic acid (2)} have been measured at T = (293.15–313.15) K and at P = 0.1 MPa. The theoretical thermodynamic properties of excess molar volumes (VmE), isentropic compressibility (ks), deviation in isentropic compressibility (Δks), and intermolecular free length (Lf) are calculated using experimental density and speed of sound data. The VmE and Δks values for both binary mixtures were found to be negative over the entire mole fraction range of composition at all the investigated temperatures. These results suggest the existence of specific interactions between components in the molecules. The experimental data could be helpful to understand the molecular interactions between the IL and carboxylic acid combinations. The experimental data were fitted to the Redlich–Kister polynomial equation.Item Cobalt boron nitride : a novel heterogeneous catalyst for the synthesis of medicinally important α-amino quinoline phosphonates(Taylor and Fancis, 2016) Sureshkumar, M; Anand, Krishnan; Muthu, T.; Gengan, Robert MoonsamyA novel cobalt supported on boron nitride (CoBNT) heterogeneous catalyst for the synthesis of α-amino quinoline phosphonates (AQPs) is reported in the present work. The CoBNT was synthesised by simply mix-ing boron nitride in a solution of cobalt acetate, under an inert atmosphere for 7 d followed by filtration; the yield was 94%. It exhibited excellent catalytic properties for the synthesis of 16 novel AQPs in a one pot mixture containing 2-methoxy 3-formyl quinoline, aniline derivatives and diethyl phosphite. Reactions were rapid, products were easily worked-up and were obtained in more than 90% yield. The CoBNT also exhibited higher catalytic activity than conventional catalysts and was re-used five times without significant decrease in catalytic activity.Item Biosynthesis of palladium nanoparticles by using Moringa oleifera flower extract and their catalytic and biological properties(Elsevier, 2016) Anand, Krishnan; Tiloke, Charlette; Phulukdaree, Alisa; Ranjan, B.; Chuturgoon, Anil A.; Singh, S.; Gengan, Robert MoonsamyThe biosynthesis of nanostructured biopalladium nanoparticles (PdNPs) from an aqueous solution of crystalline palladium acetate is reported. For the synthesised PdNPs in solution, an agroforest biomass waste petal of Moringa oleifera derived bis-phthalate was used as natural reducing and biocapping agents. Continuous absorp-tion in the UV region and subsequent brown colour change confirmed the formation of PdNPs. A strong surface plasmon peak for PdNPs occurred at 460 nm. PdNPs were characterized by SEM with EDX, FTIR, TEM and DLS. The chemical composition of the aqueous extract was determined by GC–MS coupled with FTIR and 1NMR. The cat-alytic degradation effect by PdNPs on industrial organic toxic effluents p-nitrophenol (PNP) and methylene blue dye was monitored by UV Spectroscopy. On the other hand PdNPs catalysed the base mediated suzuki coupling reaction for biphenyl synthesis, in water. Moreover, PdNPs were found to be reusable catalysts. Toxicity studies of PdNPs showed that the death of brine shrimp to be b50%. Therefore, PdNPs displayed potential for further anti-cancer studies via tumour cell lines. The in vitro cytotoxicity evaluation of the extract capped nanoparticles was carried out using human lung carcinoma cells (A549) and peripheral lymphocytes normal cells by MTT cell via-bility assay. Also, PdNPs showed antibacterial activity against Enterococcus faecalis among the different tested strains, including Bacillus cereus, Staphylococcus aureus, Esherichia coli and Candida albicans, Candida utilis.Item Synthesis, characterization and thermophysical properties of ionic liquid N-methyl-N-(2′,3′-epoxypropyl)-2-oxopyrrolidinium chloride and its binary mixtures with water or ethanol at different temperatures(Elsevier, 2016) Vasanthakumar, Arumugam; Bahadur, Indra; Redhi, Gan G.; Gengan, Robert Moonsamy; Anand, KrishnanA novel ionic liquid, namely, N-methyl-N-(2′,3′-epoxypropyl)-2-oxopyrrolidiniumchloride [Epmpyr]+[Cl]− was synthesized and characterized by different techniques such as NMR (1H and 13C), FTIR, and elemental analysis. The water content of the ionic liquid was checked by Karl Fisher titration. Further, the density, ρ, and speed of sound, u, were measured for the above ionic liquid and the corresponding binary systems with water or ethanol at different temperatures ranging from (293.15 to 313.15) K. The derived thermodynamic properties for instance excess molar volumes, VE m isentropic compressibility, κs, and deviation in isentropic compressibility, Δκs, were investigated from the density and speed of sound data, respectively. It is noted that density and speed of sound of the ionic liquid and its binary mixtures were decreased with increase in temperature, whereas excess molar volume, isentropic compressibility, and deviation in isentropic compressibility values increased. Derived properties such as excess molar volumes, and deviation in isentropic compressibility data were fitted to the Redlich-Kister polynomial equation. The measured and calculated data were interpreted in terms of intermolecular interfaces and structural effects between similar and dissimilar molecules upon mixing.