The synthesis of an α-azaornithine derivative and its reaction with trypsin

Gray, C.J.; Parker, Richard C.

doi:10.1016/0040-4020(75)80315-2

Cited by 17 publications

(12 citation statements)

References 16 publications

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“…In this study, nine different N-phenyl-1,3,4-thiadiazole compounds derived from α-methyl cinnamic acid was synthesized and, their structures were elucidated by using FT-IR (Fourier Transform Infrared spectroscopy), 1 H-NMR (Proton nuclear magnetic resonance spectroscopy), 13 C-NMR (Carbon-13 nuclear magnetic resonance spectroscopy) and UV-Vis (Ultraviolet-Visible) spectroscopic methods. In addition, the molecular and electronic properties as well as UV-Vis absorptions of these compounds have been theoretically calculated and analyzed.…”

Section: S N N Nh 2 Rmentioning

confidence: 99%

Synthesis and Charactezation of Some New 1,3,4-Thiadiazole Compounds Derived from α-methyl Cinnamic Acid and their DFT Studies

Gür¹,

Şener²

2017

ANADOLU UNIVERSITY JOURNAL OF SCIENCE AND TECHNOLOGY a - Applied Sciences and Engineering

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Some novel 1,3,4-thiadiazole compounds derived from α-methyl cinnamic acid was synthesized, in this study. The structures of these compounds were elucidated by using spectroscopic methods such as FT-IR spectroscopy, 1 H-NMR spectroscopy, 13 C-NMR spectroscopy. Then, the absorption characteristics of the compounds were also examined by using UV-Vis spectrophotometer. In addition, the geometrical and electronic properties as well as Ultraviolet Visible analyzes of the compounds were theoretically done by using the density functional theory. The electronic configurations of the compounds substituted fluoro, chloro and methoxy have been investigated and how to effect chemical reactivity parameters to this configuration have been analyzed by using frontier molecular orbital energies. The calculated values obtained by B3PW91 with 6-311++G basis set and B3LYP with cc-PVTZ basis set are in good agreement with the experimental data. The results show that the UV-Vis absorptions are noticeably influenced by the o-, m-or p-positions of Cl, F and methoxy substituents. The methoxy substituent has more effect on the LUMO energies when compared to the Cl and F substituents. Moreover, positions of the substituents in the isomeric compounds were found to influence the molecular electronegativity and absorption wavelength. The absorption wavelength has the greatest value as the electronegativity of the isomer structures in the p-position of the substituents is smaller.

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Section: S N N Nh 2 Rmentioning

confidence: 99%

Synthesis and Charactezation of Some New 1,3,4-Thiadiazole Compounds Derived from α-methyl Cinnamic Acid and their DFT Studies

Gür¹,

Şener²

2017

ANADOLU UNIVERSITY JOURNAL OF SCIENCE AND TECHNOLOGY a - Applied Sciences and Engineering

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“…Furthermore, the aromaticity of the thiadiazoles contributes to a decreased toxicity and an improved durability in the living organism [5]. Many methods have been described for the synthesis of 1,3,4-thiadiazole compounds, where the most common starting materials are as follows: thiosemicarbazites, thiocarbazides, dithiocarbazates, thioacylhydrazines, acylhydrazines and bitolyure derivatives [6][7][8][9][10][11][12][13][14]. Furthermore, some of the properties of thiadiazole and its derivatives have been successfully studied using quantum mechanical calculations [15][16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

“…The alkenic C7 and C8 atoms were respectively found in around 119.74-127.56 and 122.79-132.47 ppm. For compounds III and IV, the C18 atoms were observed at 50.68 ppm and 47.16 and 34.52 ppm, respectively.Table 3 13. C-NMR data of compounds I-IV (δ, ppm, DMSO-d6).…”

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confidence: 99%

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New 1,3,4-thiadiazole compounds: synthesis, spectroscopic characterisation and theoretical analyses based on DFT calculations

Çavuş¹,

Muğlu²

2018

Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi

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In this study, four novel 1,3,4-thiadiazole compounds, derived from α-methyl cinnamic acid, were synthesised. The structural elucidation was carried out using UV-Vis, FT-IR, 1H-NMR and 13C-NMR spectroscopy. In addition, the chemical and electronic properties of the compounds as well as UV-Vis, IR and NMR analyses were theoretically performed using the density functional theory (DFT). Based on the frontier molecular orbital (FMO) energies of the compounds, which were obtained from different methods and basis sets, some chemical reactivity parameters and their relationship with the methods were analysed. Theoretical calculations were compared with the experimental results. The electronegative substituents Cl and NO2 reduced the HOMO-LUMO energy gap (∆E), and the ones caused a bathochromic shift in the UV absorption wavelength. The Pearson correlation coefficients between the experimental and theoretical IR and 13C NMR results were approximately R = 0.99. It was seen that, the chemical shift of hydrogen bound to an electronegative nitrogen atom was affected by intarmolecular hydrogen bond interactions.

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“…Moreover, introduction of an 'aza' residue near the scissile peptide bond of a peptidase substrate could give a compound with competitive or mechanismbased inhibitory activity. Enzyme inhibitors with azapeptide structure have been developed for serine proteases such as trypsin [5,6], thrombin [6] and human leucocyte elastase [7] and cysteine proteases [8,9]. Renin inhibitors with statine structure, together with an azaamino acid residue, have been prepared [10] and azaamino acid residues were used in the design of ACE inhibitors [11] and [3-1actamase inhibitors [12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of azaproline peptides as potential inhibitors of dipeptidyl peptidase IV and prolyl oligopeptidase

et al. 1995

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The synthesis of an α-azaornithine derivative and its reaction with trypsin

Cited by 17 publications

References 16 publications

Synthesis and Charactezation of Some New 1,3,4-Thiadiazole Compounds Derived from α-methyl Cinnamic Acid and their DFT Studies

Synthesis and Charactezation of Some New 1,3,4-Thiadiazole Compounds Derived from α-methyl Cinnamic Acid and their DFT Studies

New 1,3,4-thiadiazole compounds: synthesis, spectroscopic characterisation and theoretical analyses based on DFT calculations

Synthesis and evaluation of azaproline peptides as potential inhibitors of dipeptidyl peptidase IV and prolyl oligopeptidase

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