scholarly journals Synthesis of (2Z)-4,6-Diphenyl-N-((2-(Piperidin-1-yl)Ethyl]-2H-1,3-Thiazin-2-Imino Hydrochloride and its Antimicrobial Activities

Author(s):  
Oluwaseyi Bukky Ovonramwen ◽  
Bodunde Joseph Owolabi ◽  
Amowie Philip Oviawe

Aim: The study aims to synthesize, characterize, and screen (2Z)-4,6-diphenyl-N-((2-(piperidin-1-yl)ethyl]-2H-1,3-thiazin-2-imino hydrochloride for microbial activities. Methodology: A (2Z)-4,6-diphenyl-N-((2-(piperidin-1-yl)ethyl]-2H-1,3-thiazin-2-imino hydrochloride was synthesized via two-steps reaction from chalcone using acetophenone and benzaldehyde, further cyclized with thiourea and later N-alkylated with 1-(2-chloroethyl)piperidine hydrochloride, its purity was tested by thin-layer chromatography (TLC) and characterized by Fourier transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance (NMR) and nuclear magnetic resonance (13C-NMR) and screened against Pseudomonas aeruginosa, Escherichia coli, Bacillus subtilis, methicillin-susceptible Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, and Candida albicans using the standard microbiological method. Results: A golden yellow needle-like crystals (2Z)-4,6-diphenyl-N-((2-(piperidin-1-yl)ethyl]-2H-1,3-thiazin-2-imininium hydrochloride with Rf, 7 EtOAc: 3 Pet (0.75) and MP, 285-287oC was synthesized and the in vitro antimicrobial study of the compound exhibited moderate activities in comparison with standard ciprofloxacin and itraconazole. Conclusion: A new (2Z)-4,6-Diphenyl-N-((2-(piperidin-1-yl)ethyl]-2H-1,3-thiazin-2-imininium hydrochloride was synthesized using Claisen-Schmidt condensation, Michael addition and N-alkylation shows moderate antimicrobial activities against E. coli, B. subtilis, methicillin-susceptible S. aureus, methicillin-resistant S. aureus and C. albicans.

Molbank ◽  
10.3390/m1213 ◽  
2021 ◽  
Vol 2021 (2) ◽  
pp. M1213
Author(s):  
Paolo Coghi ◽  
Jerome P. L. Ng ◽  
Ali Adnan Nasim ◽  
Vincent Kam Wai Wong

The 1,2,3-triazole is a well-known biologically active pharmacophore constructed by the copper-catalyzed azide–alkyne cycloaddition. We herein reported the synthesis of 4-amino-7-chloro-based [1,2,3]-triazole hybrids via Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of 4-azido-7-chloroquinoline with an alkyne derivative of acetaminophen. The compound was fully characterized by Fourier-transform infrared (FTIR), proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), heteronuclear single quantum coherence (HSQC), ultraviolet (UV) and high-resolution mass spectroscopies (HRMS). This compound was screened in vitro with different normal and cancer cell lines. The drug likeness of the compound was also investigated by predicting its pharmacokinetic properties.


1990 ◽  
Vol 36 (2) ◽  
pp. 225-229 ◽  
Author(s):  
K R Copeland ◽  
R W Yatscoff ◽  
R M McKenna

Abstract Eight cyclosporine (CsA) metabolites were isolated from the urine of renal-transplant patients by high-pressure liquid chromatography. Structure and purity of the metabolites were assessed by fast atomic bombardment/mass spectroscopy, by proton nuclear magnetic resonance (NMR), and, when the quantity of metabolites permitted, by 13C-NMR. The immunosuppressive activities (I) of the metabolites were tested in three separate in vitro systems: primary and secondary mixed lymphocyte reactions as well as by a mitogen-stimulated system. The I, as measured by comparing the concentration of each metabolite required for 50% inhibition of incorporation of [3H] thymidine, varied among the assay systems, as did the ranking of I among the test systems. In general, the I of most metabolites in all assay systems were less than 10% of that for CsA. Metabolites with single modifications exhibited the greatest I; e.g., that of M-17 was congruent to 16% of that of CsA (potency ratio 0.16) in a secondary mixed lymphocyte reaction. The significance of these findings in relation to therapeutic monitoring of CsA is discussed.


1985 ◽  
Vol 39 (1) ◽  
pp. 25-30 ◽  
Author(s):  
Danny O. Jacobs ◽  
Scott O. Trerotola ◽  
R.Gregg Settle ◽  
Rolando H. Rolandelli ◽  
Gerald L. Wolf ◽  
...  

1995 ◽  
Vol 49 (10) ◽  
pp. 1474-1477 ◽  
Author(s):  
Jim Liang ◽  
Mark Roselius ◽  
David W. Johnson

The residual hydrogen content of several perfluoropolyalkylether base fluids has been determined with the use of proton nuclear magnetic resonance (NMR) and Fourier transform infrared (FT-IR) spectroscopies. The analysis of standard samples gives a linear calibration curve for hydrogen concentrations between 0.5 and 500 ppm for both FT-IR and NMR. The two methods have similar detection limits of about 1 ppm. Analysis of identical samples of Krytox 143 AC and Krytox 143 AZ by both methods gives results which are in excellent agreement. The two methods also provide information about the chemical environment in which the hydrogen is located. In both of the Krytox samples, the hydrogen is located in CFH groups within the polymer chain.


2018 ◽  
Vol 31 (6) ◽  
pp. 694-706 ◽  
Author(s):  
Dejin Tong ◽  
Haipeng Wang ◽  
Lei Chen ◽  
Lei Wang ◽  
Zhanxiong Li

Linear carborane-carbosilane-phenylacetylene polymers have been synthesized as precursors for ceramic and characterized by Fourier transform infrared (FT-IR), proton nuclear magnetic resonance (1H-NMR), and carbon-nuclear magnetic resonance (13C-NMR). Novel linear polymers have the advantage of being extremely easy to process and convert into ceramics, since they are either viscous liquids or low melting solids at room temperature and are soluble in most organic solvents. Ceramic conversion reaction of the polymers was studied, and the conversion mechanism using thermogravimetric analyzer, FT-IR, and pyrolysis-gas chromatography-mass spectrometry was proposed. During the early heating period in the mechanism, the precursor polymer is cured and oligomer is formed. Then the degradation of oligomer takes place at higher temperatures with the weak bond cleaved and cross-linked simultaneously. Ceramic yield of the polymer after heating up to 1000°C in nitrogen (N2) was 77.6%. The derived ceramics exhibit excellent thermal and thermo-oxidative stability, whose 5% mass loss temperature was identified to be 650°C in N2 and 665°C in air, respectively. Boron appears to be the key element to achieve the outstanding thermo-oxidative stability. The relevant kinetic data were obtained by two kinds of model-free-kinetic algorithms, differential Friedman and integral Kissinger–Akahira–Sunose. These two methods were combined to give the energy profile, which has been identified to be a function of the transformation degree ( α), since the energy demand at each degradation stage is different depending on α.


Molbank ◽  
10.3390/m1192 ◽  
2021 ◽  
Vol 2021 (1) ◽  
pp. M1192
Author(s):  
Reshma Sathyanarayana ◽  
Boja Poojary

Ethyl 4-(butylamino)-3-nitrobenzoate upon “one-pot” nitro-reductive cyclization using sodium dithionite and substituted aldehyde in dimethyl sulphoxide affords ethyl 1-butyl-2-(2-hydroxy-4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate in an 87% yield. The structural characterization was determined by Fourier-transfer infrared spectroscopy (FT-IR), Proton nuclear magnetic resonance (1H-NMR) , Carbon-13 nuclear magnetic resonance (13C-NMR), mass spectrometry, Ultraviolet-visible(UV-Vis), photoluminescence (PL), thin-film solid emission spectra, cyclic voltammetry (CV) and thermogravimetric (TGA) analysis. Molecular electrostatic potential (MEP) was studied to determine the reactive sites of the molecule.


2021 ◽  
Vol 12 (1) ◽  
pp. 56-59
Author(s):  
Mohammed Bahreldin Hussein ◽  
Muna Mahdi Mohammed ◽  
Abdalla Gobara ◽  
Asha Fadllallah Wady ◽  
Awad Salim Ibrahim Holy

Schiff bases are versatile ligands, synthesized via condensation of primary amines with carbonyl compounds. In this study, equimolar amounts of 4-imidazolecarboxaldehyde and thiosemicarbazide were combined and the Schiff base 4-imidazolecarboxaldehyde thiosemicarbazone was prepared as a new bidentate complexing agent. The synthesized ligand was reacted with palladium (II) and platinum (II) ions yielding air-stable complexes. For characterization purpose, infrared spectra, mass spectra, electronic spectra, thermal analysis, proton nuclear magnetic resonance and 13-carbon nuclear magnetic resonance spectra studies were carried out on the obtained complexes and ligand. The characterization data showed that the ligand acts as a bidentate coordinate to the metal ions through azomethine nitrogen and sulfur atoms. An in vitro antimicrobial investigation was also carried out for the free ligand and its metal complexes against four bacteria; Bacillus cereus, Staphylococcus aureus (Gram-positive), Escherichia coli and Salmonella typhimurium (Gram-negative) and one Fungi; Candida albicans, to assess their antimicrobial properties by disc diffusion technique. Antimicrobial activity of the prepared complexes showed higher activity than the free ligand.


Polymers ◽  
2021 ◽  
Vol 13 (6) ◽  
pp. 852
Author(s):  
David Alejandro González Martínez ◽  
Enrique Vigueras Santiago ◽  
Susana Hernández López

Carbonation of epoxidized linseed oil (CELO) containing five-membered cyclic carbonate (CC5) groups has been optimized to 95% by reacting epoxidized linseed oil (ELO) with carbon dioxide (CO2) and tetrabutylammonium bromide (TBAB) as catalysts. The effect of reaction variables (temperature, CO2 pressure, and catalyst concentration) on the reaction parameters (conversion, carbonation and selectivity) in an autoclave system was investigated. The reactions were monitored, and the products were characterized by Fourier Transform Infrared Spectroscopy (FT-IR), carbon-13 nuclear magnetic resonance (13C-NMR) and proton nuclear magnetic resonance (1H-NMR) spectroscopies. The results showed that when carrying out the reaction at high temperature (from 90 °C to 120 °C) and CO2 pressure (60–120 psi), the reaction’s conversion improves; however, the selectivity of the reaction decreases due to the promotion of side reactions. Regarding the catalyst, increasing the TBAB concentration from 2.0 to 5.0 w/w% favors selectivity. The presence of a secondary mechanism is based on the formation of a carboxylate ion, which was formed due to the interaction of CO2 with the catalyst and was demonstrated through 13C-NMR and FT-IR. The combination of these factors makes it possible to obtain the largest conversion (96%), carbonation (95%), and selectivity (99%) values reported until now, which are obtained at low temperature (90 °C), low pressure (60 psi) and high catalyst concentration (5.0% TBAB).


2018 ◽  
Vol 24 (4) ◽  
pp. 193-196 ◽  
Author(s):  
Mehdi Ahmadi Sabegh ◽  
Jabbar Khalafy

AbstractThe oxidation of 1,4-diacetylbenzene using several oxidizing agents gave 1,4-phenylene-bis-glyoxal in 61–85% yields. A convenient and efficient synthesis of bis-quinoxaline and bis-pyrido[2,3-b]pyrazine derivatives involves the double condensation of 1,2-diamines with 1,4-phenylene-bis-glyoxal in ethanol under reflux conditions. The structures of the new products were defined by proton nuclear magnetic resonance (1H NMR), carbon-13 nuclear magnetic resonance (13C NMR), Fourier-transform infrared spectroscopy (FT-IR) and mass spectrometry (MS).


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