Yeon Tae Jeong

A facile synthesis, antibacterial, and antitubercular studies of some piperidin-4-one and tetrahydropyridine derivatives.

The raise in clinical significance of multidrug-resistant bacterial pathogens has directed us to synthesize 2,6-diarylpiperidin-4-one and Delta(3)-tetrahydropyridin-4-ol based benzimidazole and O-arylsulfonyl derivatives. X-ray crystal structure of tetrahydropyridinol (23) confirmed a change in conformation and orientation of substituents upon amide formation. Antibacterial activities evaluated against a wide number of bacterial pathogens (both sensitive and multidrug-resistant) revealed that 19, 27 against Staphylococcus aureus, 27 against Enterococcus faecalis, and 19, 21, 23, and 27 against Enterococcus faecium are significantly good at lowest MIC(90) (16 microg/mL). Inhibitory power noticed by 23 against Vancomycin-Linezolid-resistant E. faecalis and 27 against Vancomycin-resistant E. faecium are onefold better than the standard Linezolid and Trovafloxacin drugs, respectively. Moreover, antitubercular activity for the selected compounds against Mycobacterium tuberculosis H37Rv revealed that compounds 23, 24, and 27 expressed onefold improved potency compared to the standard Rifampicin drug.

Facile covalent immobilization of cadmium sulfide quantum dots on graphene oxide nanosheets: preparation, characterization, and optical properties

A facile approach for the preparation of a novel hybrid material containing graphene and an inorganic semiconducting material, cadmium sulfide quantum dots (CdS QDs), is demonstrated for the first time. First, amino-functionalized CdS QDs were prepared by modifications of the kinetic trapping method. Then, pristine graphite was oxidized and exfoliated to obtain graphene oxide nanosheets (GONS), which were then acylated with thionyl chloride to introduce acyl chloride groups on their surface. Subsequently, immobilization of the CdS QDs on the GONS surface was achieved through an amidation reaction between the amino groups located on the CdS QDs surface and the acyl chloride groups bound to the GONS surface. Fourier transform infrared spectroscopy (FT-IR), (1)H nuclear magnetic resonance ((1)H-NMR), x-ray diffraction (XRD), x-ray photoelectron spectroscopy (XPS), and energy dispersive x-ray (EDX) spectroscopy were employed to investigate the changes in the surface functionalities, while high resolution transmission electron microscopy (HR-TEM) and field emission scanning electronic microscopy (FE-SEM) were used to study the morphologies and distribution of the CdS QDs on the GONS surface. Thermogravimetric analysis (TGA) was employed to characterize the weight loss of the samples on heating. Photoluminescence (PL) measurements were used to study the optical properties of the prepared CdS QDs and the CdS-graphene hybrid material.

Synthesis, spectral and biological evaluation of some new thiazolidinones and thiazoles based on t-3-alkyl-r-2,c-6-diarylpiperidin-4-ones.

A stereospecific synthesis of some thiazolidinones and thiazoles was achieved conveniently through certain alpha-halo keto agents and reactivity of chloroacetyl chloride was successfully enhanced by CsF-Celite+CH(3)COONa. NMR studies revealed that the configuration of N-N bond is found to be anti with respect to C-3 alkyl group while C=N bond in thiazolidinone is trans with respect to N-N bond. Antimycobacterial activity tested against Mycobacterium tuberculosis indicated that compounds 19, 20, 24, 29, 30 and 32 exhibited twofold enhanced potency than Rifampicin. Similarly, antimicrobial screening studies pointed out that compounds 21 and 28 exceptionally noticed promising activities and particularly, 21 against Staphylococcus aureus and, 24 and 32 against Rhizopus sp. exhibited onefold elevated inhibition potency whereas 21 against Klebsiella pneumoniae showed twofold improved potency than Ciprofloxacin and Amphotericin B.

Synthesis and spectral characterization of a new class of N-(N-methylpiperazinoacetyl)-2,6-diarylpiperidin-4-ones: Antimicrobial, analgesic and antipyretic studies

A series of N-(N-methylpiperazinoacetyl)-2,6-diarylpiperidin-4-ones (13c-21c) were synthesized by the base catalyzed nucleophilic substitution of N-chloroacetyl-2,6-diarylpiperidin-4-ones obtained from their corresponding 2,6-diarylpiperidin-4-ones with N-methylpiperazine. These newly synthesized compounds were characterized by one- and two-dimensional NMR spectral studies. In all the cases, the piperazine ring adopted normal chair conformation with equatorial orientation of methyl group irrespective of the non-chair conformations of the piperidin-4-one moiety. All the compounds were screened for their possible antibacterial and antifungal activities against a spectrum of microbial agents besides analgesic and antipyretic activities. These biological studies proved that compounds 17c/18c against bacterial and 18c/20c against fungal strains exhibited promising antimicrobial activities whereas 17c/19c and 18c/19c showed beneficial analgesic and antipyretic profiles, respectively, at a concentration of 60mg/kg and were also found to be more potent than the reference drug.

Electrochemical supercapacitors based on a novel graphene/conjugated polymer composite system

An efficient method for the preparation of a highly conducting hybrid material from graphene oxide nanosheets (GNS) and a novel conjugated polymer, poly(3,4-propylenedioxythiophene), is demonstrated. A functionalized monomer based on 3,4-propylenedioxythiophene, namely ProDOT–OH, was covalently functionalized with GNS, followed by oxidative polymerization to prepare GNS-f-PProDOT composites. The covalent functionalization process of GNS with the monomer ProDOT–OH was activated through the simple esterification reaction between the acyl chloride derivative on the nanosheets and the pendant hydroxyl group present in the monomer. Furthermore, the monomer functionalized GNS were co-polymerized with thiophene resulting in hybrid graphene nanostructures coated with highly conducting co-polymers with a room temperature electrical conductivity as high as 22.5 S cm−1. The resulting hybrid materials were characterized using a range of analytical techniques. The specific capacitance value of the composite and the co-polymer hybrids at a scan rate of 10 mV s−1 has been determined to be 158 and 201 F g−1 respectively and hence particularly promising for supercapacitors.

Synthesis, spectral, crystal structure and in vitro antimicrobial evaluation of imidazole/benzotriazole substituted piperidin-4-one derivatives.

Imidazole/benzotriazole analogues substituted piperidin-4-one derivatives (17-26) have been synthesized. Their chemical structures were characterized by IR, 1H NMR, 13C NMR and mass spectral analysis. In addition, single crystal X-ray diffraction has also been recorded for compounds 21 and 23. The synthesized compounds were subjected to their in vitro antibacterial and antifungal activities against pathogenic microbial strains. The results pointed out that compounds 19 & 24 against B. subtilis and 20 & 24 against E. coli were explored superior inhibition activity.

Novel amino-acid-based polymer/multi-walled carbon nanotube bio-nanocomposites: highly water dispersible carbon nanotubes decorated with gold nanoparticles

A well-reproducible and completely green route towards highly water dispersible multi-walled carbon nanotubes (MWNT) is achieved by a non-invasive, polymer wrapping technique, where the polymer is adsorbed on the MWNTs surface. Simply mixing an amino-acid-based polymer derivative, namely poly methacryloyl beta-alanine (PMBA) with purified MWNTs in distilled water resulted in the formation of PMBA-MWNT nanocomposite hybrids. Gold nanoparticles (AuNPs) were further anchored on the polymer-wrapped MWNTs, which were previously sonicated in distilled water, via the hydrogen bonding interaction between the carboxylic acid functional groups present in the polymer-modified MWNTs and the citrate-capped AuNPs. The surface morphologies and chemistries of the hybrids decorated with nanoparticles were characterized by transmission electron microscopy (TEM) and UV-visible absorption spectroscopy. Additionally, the composites were also prepared by the in situ free radical polymerization of the monomer, methacryloyl beta-alanine (MBA), with MWNTs. Thus functionalized MWNTs were studied by thermogravimetric analysis (TGA), field emission scanning electron microscopy (FE-SEM) and TEM. Both methods were effective in the nanotube functionalization and ensured good dispersion and high stability in water over three months. Due to the presence of the high densities of carboxylic acid functionalities on the surface of CNTs, various colloidal nanocrystals can be attached to MWNTs.

Stereospecific synthesis of oximes and oxime ethers of 3-azabicycles: a SAR study towards antimicrobial agents.

Libraries of 1-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/O-methyloximes 1-14/15-28/29-42 and 7-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/O-methyloximes 43-48/49-54/55-60 were synthesized and their stereochemistry was established by 1D/2D NMR spectral and single crystal XRD studies. All the synthesized oximes and oxime ethers were screened for their in vitro antimicrobial activity against a panel of pathogenic bacteria (Bacillus subtilis, Staphylococcus aureus, Klebsiella pneumoniae and Pseudomonas aeruginosa) and fungi (Candida albicans, Candida parapsilosis, Aspergillus niger and Cryptococcus neoformans) using Gentamicin and Fluconazole as standards, respectively. From the SAR profile, the lead molecules were identified.

Synthesis, crystal and antibacterial studies of diversely functionalized tetrahydropyridin-4-ol.

In an effort to expand the spectrum of antibacterial activity associated with piperidin-4-one derivatives, we have synthesized two series of 3-carboxyethyl-2,6-diphenyl-4-hydroxy-Delta(3)-tetrahydropyridine derivatives bearing diversified heterocyclic and aromatic systems at the nitrogen atom through acetyl (6-18) and 2-propanoyl (9-31) linkers. Unlike acetyl derivatives, NMR spectral pattern of the propanoyl counterparts revealed the existence of pair of rotational isomers (syn and anti) in solution at room temperature due to the hindered rotation about N-CO bond. X-ray crystal studies of 9 and 24 clearly pointed out that all the compounds existed in only one form particularly, in stable syn form in solid state. Each of the compounds was screened for their in vitro antibacterial activity against nine human pathogenic gram-positive strains including multiple drug resistant organisms and seven problematic gram-negative strains. Among the various heterocycles examined here, imidazole substituted derivatives 12 and 25 exhibited antibacterial activity approaching that of Linezolid and Trovafloxacin drugs particularly against multiple resistant Enterococcus faecium-VanA phenotype strains.

Preparation and properties of semifluorinated block copolymers of 2-(dimethylamino)ethyl methacrylate and fluorooctyl methacrylates

Semifluorinated block copolymers of poly(2-(dimethylamino)ethyl methacrylate) (PDMAEMA) and poly(fluorooctyl methacrylates) (PFOMA) were prepared using group transfer polymerisation via sequential monomer addition. Wide ranges of copolymers were obtained with good control over both molecular weight and composition by adjusting the monomers/initiator ratio. The micellar characteristics of the copolymers in water and chloroform were investigated by quasi-elastic light scattering and transmission electron microscopy. The size and morphologies of micelles were greatly influenced by copolymer composition, pH, and temperature. In addition, the solubility of copolymers and the formation of water-in-carbon dioxide (W/C) microemulsions were described in terms of the cloud points. The block copolymers exhibited the excellent ability of stabilizing W/C microemulsions.