scholarly journals Crystal Structure and Spectroscopic Analysis of the Compatible Solute Nγ-Acetyl-L-2,4-Diaminobutyric Acid

Crystals ◽  
2020 ◽  
Vol 10 (12) ◽  
pp. 1136
Author(s):  
Lea Martin ◽  
Wilhelm Klein ◽  
Sebastian P. Schwaminger ◽  
Thomas F. Fässler ◽  
Sonja Berensmeier
Keyword(s):  
Crystal Structure ◽  
Spectroscopic Analysis ◽  
Compatible Solutes ◽  
13C Nmr Spectroscopy ◽  
Water Soluble ◽  
Low Molecular Weight ◽  
1H And 13C Nmr ◽  
Diaminobutyric Acid ◽  
Cooling Crystallization

Compatible solutes are low molecular weight, highly water-soluble and neutrally net-charged molecules with various protective functionalities that accumulate and are produced in microorganisms. Their multi-purpose functionalities, also adaptable in vitro, make them potential components in healthcare and cosmetic products. One promising but insufficiently examined representative of this molecule class is Nγ-acetyl-L-2,4-diaminobutyric acid (γ-NADA), the metabolic precursor of ectoine. Here, we demonstrate the crystallization ability of γ-NADA by using cooling crystallization in aqueous solvents and find that it forms rod-shaped crystals. According to a single crystal structure determination, γ-NADA is orthorhombic with space group P212121 and a = 5.3647(1), b = 8.3652(2), c = 16.9149(5) Å, Z = 4, R1 = 3.48%, wR2 = 7.33% (all data). Additionally, γ-NADA is analyzed via Raman, IR, 1H, and 13C NMR spectroscopy.

scholarly journals Synthesis and In Vitro Antimicrobial Evaluation of Photoactive Multi—Block Chalcone Conjugate Phthalimide and 1,8-Naphthalimide Novolacs

Polymers ◽  
2021 ◽  
Vol 13 (11) ◽  
pp. 1859
Author(s):  
Periyan Durairaju ◽  
Chinnasamy Umarani ◽  
Govindasami Periyasami ◽  
Perumberkandigai Adikesavan Vivekanand ◽  
Mostafizur Rahaman
Keyword(s):  
Spectroscopic Analysis ◽  
Photophysical Properties ◽  
Gel Permeation Chromatography ◽  
13C Nmr Spectroscopy ◽  
Antimicrobial Activities ◽  
Microbial Activities ◽  
E Coli ◽  
Molecular Weights ◽  
Antimicrobial Evaluation

Herein we report new multiblock chalcone conjugate phthalimide and naphthalimide functionalized copolymers with a topologically novel architecture synthesis using nucleophilic substitution and polycondensation methodology. The structures of the synthesized novolacs were elucidated on the basis of their spectroscopic analysis including FTIR, 1H NMR, and 13C NMR spectroscopy. Further, the number-average and weight-average molecular weights of the novolac polymers were determined by gel permeation chromatography (GPC). We examined the solubility of the synthesized polymers in various organic solvents including CHCl3, CH3CN, THF, H2O, CH3OH, DMSO, and DMF and found they are insoluble in both methanol and water. The novolac polymers were evaluated for their photophysical properties and microbial activities. The investigation of the antimicrobial activities of these polymers reveals significant antimicrobial activity against the pathogens E. coli, S. aureus, C. albicans, and A. niger.

scholarly journals NEW PHARMACOLOGICALLY ACTIVE COMPOUNDS BASED ON 5-HYDROXY-7-METHOXY-2-PHENYLCHROMAN-4-ONE

2021 ◽  
Vol 3 ◽  
pp. 119-127
Author(s):  
G.M. Baisarov ◽  
◽  
S.M. Adekenov ◽  
Keyword(s):  
Nmr Spectroscopy ◽  
13C Nmr ◽  
Potassium Carbonate ◽  
13C Nmr Spectroscopy ◽  
1H And 13C Nmr ◽  
Pharmacologically Active ◽  
Pharmacologically Active Compounds ◽  
First Time

The reaction of 5-hydroxy-7-methoxy-2-phenylchroman-4-one with dibromoalkanes in acetone in the presence of potassium carbonate proceeds according to the Michael’s retro-reaction O-alkylation and leads to the formation of the corresponding 2-(bromo-alkoxy) chalcones. The structure of the synthesized compounds was confirmed by IR-, 1H- and 13C-NMR spectroscopy. The cytotoxic, hepatoprotective and anti-inflammatory effects of chalcone derivatives (2-3) were studied for the first time in vitro and in vivo.

Antimicrobial Properties of Mono- and Di-fac-rhenium Tricarbonyl 2-Pyridyl-1,2,3-triazole Complexes

2016 ◽  
Vol 69 (5) ◽  
pp. 489 ◽  
Author(s):  
Sreedhar V. Kumar ◽  
Warrick K. C. Lo ◽  
Heather J. L. Brooks ◽  
Lyall R. Hanton ◽  
James D. Crowley
Keyword(s):  
Staphylococcus Aureus ◽  
Antimicrobial Properties ◽  
13C Nmr Spectroscopy ◽  
1H And 13C Nmr ◽  
X Ray Crystallography ◽  
The Family ◽  
Elemental Analyses ◽  
Solid State Structures ◽  
Rhenium Tricarbonyl

A family of mono- and di-fac-rhenium tricarbonyl 2-pyridyl-1,2,3-triazole complexes with different aliphatic and aromatic substituents was synthesized in good-to-excellent yields (46–99 %). The complexes were characterized by 1H and 13C NMR spectroscopy, infrared spectroscopy, electronic (UV-visible) spectroscopy, high-resolution electrospray mass spectrometry, and elemental analyses. In four examples, the solid-state structures of the rhenium(i) complexes were confirmed by X-ray crystallography. The family of the mono- and di-rhenium(i) complexes and the corresponding 2-pyridyl-1,2,3-triazole was tested for antimicrobial activity in vitro against both Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) microorganisms. Agar-based disk diffusion assays indicated that most of the rhenium(i) complexes were active against Staphylococcus aureus and that the cationic rhenium(i) complexes were more active than the related neutral systems. However, in all cases, the minimum inhibitory concentrations for all the complexes were modest (i.e. 16–1024 µg mL–1).

A Domino Reaction for the Synthesis of Novel 1,3-Dihydrofuro[3,4-c]pyridines from Pyridoxal and Ketones

Synthesis ◽  
2020 ◽  
Vol 53 (02) ◽  
pp. 365-370
Author(s):  
Lucas Pizzuti ◽  
Izamara Casadia ◽  
Thalita O. Daher ◽  
Sidnei Moura ◽  
Davi F. Back ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Nmr Spectroscopy ◽  
13C Nmr ◽  
Room Temperature ◽  
13C Nmr Spectroscopy ◽  
Domino Reaction ◽  
Alkyl Aryl ◽  
1H And 13C Nmr ◽  
X Ray ◽  
Pyridine Series

A convenient domino route for the synthesis of novel 1,3-dihydrofuro[3,4-c]pyridines from pyridoxal and alkyl, aryl or heteroaryl ketones under basic conditions is reported. A series of nine derivatives is obtained in 53–90% yields after stirring reactants for 48 hours at room temperature. Most products are easily isolated by filtration followed by recrystallization from ethanol. All products were fully characterized by FTIR, HRMS, and 1H and 13C NMR spectroscopy. The X-ray crystal structure of a representative example of the 1,3-dihydrofuro[3,4-c]pyridine series is also presented.

scholarly journals Synthesis and Characterization of Platinum (IV) complexes with S-alkyl Derivatives of Thiosalicylic Acid and the Crystal Structure of the S-butyl Derivative of Thiosalicylic Acid

2017 ◽  
Vol 18 (3) ◽  
pp. 195-201 ◽  
Author(s):  
Marina Z. Mijajlovic ◽  
Milos V. Nikolic ◽  
Dusan Lj. Tomovic ◽  
Andriana M. Bukonjic ◽  
Aleksandar Kocovic ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Water System ◽  
13C Nmr Spectroscopy ◽  
Monoclinic Crystal ◽  
1H And 13C Nmr ◽  
X Ray ◽  
Thiosalicylic Acid ◽  
Alkyl Derivatives ◽  
Derivatives Of

Abstract New platinum(IV)-complexes with S-alkyl derivatives of thiosalicylic acid (alkyl = benzyl-(L1), methyl-(L2), ethyl-(L3), propyl-(L4), butyl-(L5)) have been synthesized and characterized by microanalysis, infrared spectroscopy, and 1H and 13C NMR spectroscopy. Th e bidentate S,O ligand precursor, the S-butyl derivative of thiosalicylic acid (S-bu-thiosal), was prepared, and its crystal structure was determined. Single crystals suitable for X-ray measurements were obtained by slow crystallization from a DMSO-water system. S-bu-thiosal crystallized in a P21/c space group of a monoclinic crystal system with a = 8.0732 (3) Å, b = 19.6769 (4) Å, c = 8.2291 (3) Å and Z = 4. S-bu-thiosal also has a coplanar geometry.

Low Molecular Weight Branched Polyethylenimine-Graft-Lentinan as a Novel Synthetic Gene Carrier

2013 ◽  
Vol 815 ◽  
pp. 293-298
Author(s):  
Li Jing Min ◽  
Jing Fen Li
Keyword(s):  
Molecular Weight ◽  
Gel Electrophoresis ◽  
Transfection Efficiency ◽  
Gene Transfection ◽  
Water Soluble ◽  
Low Molecular Weight ◽  
Dna Migration ◽  
Branched Polyethylenimine ◽  
Soluble Polysaccharide

LMW Branched Polyethylenimine-graft-lentinan was synthesized by performing crosslinker CDI in the presence of water-soluble Polysaccharide (Mw 70,000) and polyethylenimine (PEI, Mw 600). The chemistry of the PEI-g-lentinan obtained were characterized. The results indicated that the amines of lentinan were grafted with PEI. Gel electrophoresis showed that DNA migration was retarded completely at a N/P ratio of 10/1, indicating good DNA condensation capability of PEI-g-lentinan. The cytotoxicity of PEI-g-lentinan was evaluated, and the results reflected that PEI-g-lentinan had a lower cytotoxicity than PEI (25 K). Gene transfection efficiency of PEI-g-chitosan in cos-7 cells was determined. Remarkably,PEI-g-lentinan showed a higher transfection efficiency than that of PEI (25 K) in vitro.

scholarly journals Synthesis and high in vitro cytotoxicity of some (S,S)-ethylenediamine-N,N’-di-2-propanoate dihydrochloride esters

2014 ◽  
Vol 79 (6) ◽  
pp. 649-658 ◽  
Author(s):  
Nebojsa Pantelic ◽  
Bojana Zmejkovski ◽  
Tatjana Stanojkovic ◽  
Verica Jeftic ◽  
Gordana Radic ◽  
...  
Keyword(s):  
K562 Cells ◽  
13C Nmr Spectroscopy ◽  
In Vitro Cytotoxicity ◽  
Myelogenous Leukemia ◽  
Antitumor Action ◽  
Human Embryonic Lung ◽  
1H And 13C Nmr ◽  
Cancerous Cell ◽  
Human Embryonic Lung Fibroblast

Novel (S,S)-R2eddip ester, O,O?-diisoamyl-(S,S)-ethylenediamine-N,N?-di-2-propanoate dihydrochloride, 1, was synthesized and characterized by IR, 1H and 13C NMR spectroscopy, mass spectroscopy and elemental analysis.In vitro antitumor action of 1, and two more R2eddip esters, O,O?-dialkyl-(S,S)-ethylenediamine-N,N?-di-2-propanoate dihydrochlorides, obtained before, (alkyl = n-Bu, n-Pe; 2 and 3, respectively), was determined against cervix adenocarcinoma (HeLa), human melanoma (Fem-x), human chronic myelogenous leukemia (K562) cells, and a non-cancerous cell line human embryonic lung fibroblast (MRC-5), using MTT assay. Esters 1-3 showed higher cytotoxicity and better selectivity in comparison to cisplatin, used as reference compound. The highest activityis expressed by1,with IC50(Fem-x)value1.51 ? 0.09 ?M.

scholarly journals Synthesis, Crystal Structure and Bioactivity of Phenazine-1-carboxylic Acylhydrazone Derivatives

Molecules ◽  
2021 ◽  
Vol 26 (17) ◽  
pp. 5320
Author(s):  
Shouting Wu ◽  
Xi Liang ◽  
Fang Luo ◽  
Hua Liu ◽  
Lingyi Shen ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Condensation Reaction ◽  
Acid Hydrazide ◽  
13C Nmr Spectroscopy ◽  
X Ray Diffraction ◽  
1H And 13C Nmr ◽  
X Ray ◽  
Thiazolyl Blue Tetrazolium Bromide ◽  
Thiazolyl Blue Tetrazolium

A phenazine-1-carboxylic acid intermediate was synthesized from the reaction of aniline and 2-bromo-3-nitro-benzoic acid. It was then esterified and reacted with hydrazine hydrate to afford phenazine-1-carboxylic hydrazine. Finally, 10 new hydrazone compounds 3a–3j were obtained by the condensation reaction of phenazine-1-carboxylic acid hydrazide and the respective aldehyde-containing compound. The structures were characterized by 1H and 13C NMR spectroscopy, MS and single crystal X-ray diffraction. The antitumor activity of the target compounds in vitro (HeLa and A549) was determined by thiazolyl blue tetrazolium bromide. The results showed that compound (E)-N′-(2-hydroxy-4-(2-(piperidine-1-yl) ethoxy) benzyl) phenazine-1-carbonyl hydrazide 3d exhibited good cytotoxic activity.

scholarly journals SYNTHESIS OF PROPERTIES N-METHYL-2-(PYRID-4-YL)-3,4-FULLEROPYRROLIDINE

2020 ◽  
Vol 2 (440) ◽  
pp. 62-68
Author(s):  
S.D. Fazylov ◽  
O.A. Nurkenov ◽  
A.E. Arinova ◽  
T.M. Seilkhanov ◽  
A.M. Gazaliev ◽  
...  
Keyword(s):  
13C Nmr ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Wide Spectrum ◽  
13C Nmr Spectroscopy ◽  
Fullerene C60 ◽  
Water Soluble ◽  
1H And 13C Nmr ◽  
Integrated Intensity ◽  
Pharmacophore Group

The article is devoted to the reactions of [2+3] cycloaddition of pyridine-4-aldehyde to fullerene C60, as well as to the preparation of its water-soluble from of the resulting reaction product N-methyl-2-(pyrid-4-yl)-3,4-fulleropyrrolidine. A literature review of organic compounds containing the pyrrolidine cycle was carried out. It is noted that such compounds have a wide spectrum of biological activity and are part of many drugs of both natural and synthetic origin. In this regard, an interesting “pharmacophore” group is the pyridine cycle, which is part of about 5% of all known drugs. The reaction of pyridin-4-aldehyde with fullerene C60 was carried out in the presence of sarcosine under the conditions of the Prato reaction. The reaction mechanism of 1,2-dipolar cycloaddition, leading to fulleropyrrolidine, is described. The water-soluble complex fulleropyrrolidinas with poly-N-vinylpyrrolidone was obtained. The structures of the synthesized compounds were studied by IR, UV, 1H and 13C NMR spectroscopy, as well as by the date of two-dimensional spectra of COSY (1H-1H) and HMQC (1H-13H). The values of chemical shifts, multiplicity and integrated intensity of 1H and 13C NMR signals in one-dimensional NMR spectra were determined. Using spectra in the formats COSY (1H-1H) and HMQC (1H-13C) homo- and heteronuclear interaction were established, confirming the structure of the studied compounds. Key words: fullerene C60, sarcosine, pyridine-4-aldehyde, fulleropyrrolidines, Prato reaction, NMR spectra.

Synthesis, characterisation, and biological activity of three new amide prodrugs of lamotrigine with reduced hepatotoxicity

2011 ◽  
Vol 65 (1) ◽  
Author(s):  
Saurabh Sinha ◽  
Prabhat Shrivastava ◽  
Sushant Shrivastava
Keyword(s):  
Side Effects ◽  
Partition Coefficients ◽  
Cell Damage ◽  
13C Nmr Spectroscopy ◽  
Glutathione Depletion ◽  
1H And 13C Nmr ◽  
In Vitro Hydrolysis ◽  
Anticonvulsant Activities ◽  
Layer Chromatography

AbstractLamotrigine (LTG) is an antiepileptic drug used for the prevention of convulsions. Except several known side effects, hepatic dysfunction is also reported. Hepatotoxic side effects occur due to the dichlorophenyl moiety which develops an abnormally low level of glutathione. Depletion of glutathione causes oxidative stress and hepatic cell damage. The goal of the present study was to test the action and side effects of the three compounds synthesised and compared to LTG. Three amide prodrugs of LTG were synthesised by its reaction with N-acetylamino acids, viz, glycine, glutamic acid, and methionine. Purified synthesised prodrugs were subjected to thin layer chromatography, melting point, solubility and partition coefficients determination and characterised by UV, FTIR, 1H and 13C NMR spectroscopy. The synthesised prodrugs were subjected to in vitro hydrolysis and to anticonvulsant and hepatotoxic activity studies. Significant reduction in hepatotoxicity and comparable anticonvulsant activities were obtained in all synthesised prodrugs as compared to LTG.

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