In this study, we exhibited an amino acid (arginine and threonine) derivative Schiff base copper(II) complexes incorporating an azobenzene moiety as a photoresponsive site and conjugated it to egg white lysozyme, a we...In this study, we exhibited an amino acid (arginine and threonine) derivative Schiff base copper(II) complexes incorporating an azobenzene moiety as a photoresponsive site and conjugated it to egg white lysozyme, a well-known protein, to change ligand conformation under binding to lysozyme. Among several spectroscopic investigations, ESR clearly showed that the nitrogen atom of the amino acid residue of lysozyme was bound to the paramagnetic copper(II) ion of the complex, and UV light irradiation confirmed photoisomerization of the azobenzene moiety of the ligand to cis-form. The binding mode was considered by means of spectroscopic as well as computational methods, whereas complete crystallographic verification was still a preliminary stage.展开更多
The dependence of electronic absorption spectra antimicrobial property on the substituent position was investigated using three Schiff bases derived from salicylaldehyde and isomeric aminobenzoic acids in three solven...The dependence of electronic absorption spectra antimicrobial property on the substituent position was investigated using three Schiff bases derived from salicylaldehyde and isomeric aminobenzoic acids in three solvents of different polarities. The absorption maxima in all three solvents exhibited dependence on the position of substituent with the absorption maxima undergoing a red shift as solvent polarity increased. The in vitro antibacterial activity of the compounds against some clinically important bacteria namely Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853), Staphylococcus aureus (ATCC 25923), Enterococcus feacalis (ATCC 29212) was determined in N,N”-dimethylformamide and 1,4-dioxane using the agar dilution method. The results revealed that the ortho and meta substituted Schiff bases exhibited better antimicrobial activity in the non-polar solvent.展开更多
Four Schiff bases, from pyruvic acid (1) with amines containing N and S donor atoms, thiocarbohydrazide (2, 61%), 2-methyl-3-thiosemicarbazide (3, 26%), S-benzyldithiocarbazate (4, 51%) and S-n-octyldithiocarbazate (5...Four Schiff bases, from pyruvic acid (1) with amines containing N and S donor atoms, thiocarbohydrazide (2, 61%), 2-methyl-3-thiosemicarbazide (3, 26%), S-benzyldithiocarbazate (4, 51%) and S-n-octyldithiocarbazate (5, 63%) have been successfully synthesized. The conventional method was used and a series of novel linear and cyclic Schiff bases were obtained with or without catalyst. All the Schiff bases were fully characterized by CHN elemental analysis, FT-IR, 1H & 13C NMR, EI-MS and two of the Schiff bases were further characterized by X-ray crystallographic structure analysis. Compound 2 crystallizes in the triclinic space group P-1 and unit cell dimensions are: a = 4.1777(8), b = 5.9538(11), c = 13.458(3) Å, α = 92.759(6), β = 90.813(6), γ = 100.040(6)°, R1 = 0.0439. Compound 3 crystallizes in the orthorhombic space group P n a 2(1) and unit cell dimensions are: a = 5.5992(2), b = 11.3962(5), c = 10.6473(5), α = 92.759(6), β = 90.813(6), γ = 100.040(6)°, R1 = 0.0285. Compounds 2 and 3 were obtained as cyclic Schiff bases which are triazine derivatives.展开更多
Glutamic acid-salicylaldehyde Schiff-base metal complexes are bound into bovine serum albumin (BSA), which afforded BSA binding Schiff-base metal complexes (BSA-SalGluM, M=Cu, Co, Ni, Zn). The BSA binding metal co...Glutamic acid-salicylaldehyde Schiff-base metal complexes are bound into bovine serum albumin (BSA), which afforded BSA binding Schiff-base metal complexes (BSA-SalGluM, M=Cu, Co, Ni, Zn). The BSA binding metal complexes were characterized by UV-vis spectra and Native PAGE. It showed that the protein structures of BSA kept after coordinating amino acid Schiff-bases metal complexes. The effect of the antioxidant activity was investigated. The results indicate that the antioxidant capacity of BSA increased more than 10 times after binding Schiff-base metal complexes.展开更多
Six new complexes of lanthanum with amino acid Schiff base ligands, A-F, were prepared in methanol-aqueous solution. The composition and properties of the title complexes were characterized by elemental analysis, mola...Six new complexes of lanthanum with amino acid Schiff base ligands, A-F, were prepared in methanol-aqueous solution. The composition and properties of the title complexes were characterized by elemental analysis, molar conductance, infrared, electronic spectra, H-1 NMR, thermogravimetric and differential thermal analysis.展开更多
Seven heterobinuclear complexes of Cu-Ln with N, N'-bis(3-carboxylsali cylidene) ethylenediamine(ES) were synthesized and characterized by elemental analysis, molar conductivity, thermogravimetry, IR and electroni...Seven heterobinuclear complexes of Cu-Ln with N, N'-bis(3-carboxylsali cylidene) ethylenediamine(ES) were synthesized and characterized by elemental analysis, molar conductivity, thermogravimetry, IR and electronic spectra. The room temperature magnetic moments show that there are basically no spin exchange interactions between the ions of Cu2+ and Ln(3+) in the CuLnESCl . nH(2)O compounds.展开更多
Condensation of eqqimolar quantities of salicylaldehyde and a-amino acid (glycine, alanine, valine, leucine, Phenylalanine, serine, cysteine) in absolute Methanol-KOH gives the amino acid Schiff base[1]. Its germanium...Condensation of eqqimolar quantities of salicylaldehyde and a-amino acid (glycine, alanine, valine, leucine, Phenylalanine, serine, cysteine) in absolute Methanol-KOH gives the amino acid Schiff base[1]. Its germanium tetrachloride adducts of the type GeCL. (sal=aa.k)2 have been prepared in absolute mothanol[2]and characterized by elemental analyses, conductance measurements, IR and 1H-NMR spectra, electronic spectra, cyclic voltammetry and thermal analyses. etc.展开更多
The title complex [Zn(L)(phen)(CH3OH)] (L = C8H6BrO4NS, aminomethanesulfonic acid 5-bromo-salicylaldelyde schiff base; phen = 1,10-phenanthroline) has been synthesized and characterized by X-ray diffraction me...The title complex [Zn(L)(phen)(CH3OH)] (L = C8H6BrO4NS, aminomethanesulfonic acid 5-bromo-salicylaldelyde schiff base; phen = 1,10-phenanthroline) has been synthesized and characterized by X-ray diffraction method. The crystal belongs to monoclinic, space group P21/c with a = 1.8712(3), b = 1.38008(19), c = 0.83685(12) nm, β = 97.791 (2)°, Mr = 569.72, V = 2.1411 (5) nm^3, Z= 4, Dc = 1.767 g/cm^3,μ = 3.151 mm^-1, F(000) = 1144, the final R = 0.0402 and wR = 0.0885. The central Zn(Ⅱ) is six-coordinated by one nitrogen and two oxygen atoms from the Schiff base, two nitrogen atoms from 1,10-phenanthroline and one oxygen from methanol to form a distorted octahedral coordination geometry.展开更多
The amino acid Schiff base complex (Sal-AMBA-Mn) was prepared with p-amino-methylbenzoic acid, salicylaldehyde and Mn(OAc)2·4H2O. Its structures was characterized with IR and UV spectra. Oxygenation mechanism of ...The amino acid Schiff base complex (Sal-AMBA-Mn) was prepared with p-amino-methylbenzoic acid, salicylaldehyde and Mn(OAc)2·4H2O. Its structures was characterized with IR and UV spectra. Oxygenation mechanism of the complex in N, N-dimethylformamide solution was investigated. The results show that lower temperature is in favor of the oxygenation, and energy, enthalpy and entropy are -3.8 kJ/mol, -4.2 J/mol and -161.44 J/(mol·K), respectively. In the presence of the manganese complex, dehydroepiandrosterone acetate is effectively oxidized by molecular oxygen and the corresponding enone 7-ketodehydroepiandrosterone acetate is obtained. The yield is 62.1% when the oxidation is carried out under the reaction conditions of 60 ℃, 2 MPa of O2 pressure, C5H5N as a solvent and molar ratio of the substrate to the complex of 1:10.展开更多
New dibutyltin(IV) complexes of Schiff base derived from 5-chloroindoline-2,3-dione, indoline- 2,3-dione with amino acids (tryptophan, alanine and valine) were synthesized and characterized by elemental analysis, IR, ...New dibutyltin(IV) complexes of Schiff base derived from 5-chloroindoline-2,3-dione, indoline- 2,3-dione with amino acids (tryptophan, alanine and valine) were synthesized and characterized by elemental analysis, IR, electronic spectra, conductance measurements, and biological activity. The analytical data showed that the Schiff base ligand acts as bidentate towards metal ions via the azomethine nitrogen and carboxylate oxygen by a stoichiometric reaction of M:L (1:2) to form metal complexes. NMR (1H, 13C and 119Sn) spectral data of the ligands and metal complex agree with proposed structures. The conductivity values between 14 - 27 ohm-1cm2mol-1 in DMF imply the presence of non-electrolyte species. 3D molecular modeling and analysis of bond lengths and bond angles have also been conducted for a representative compound, [Bu2Sn(L2)2], to substantiate the proposed structures. Antibacterial results indicate that the metal complexes are more active than the free ligands.展开更多
A general protocol for the synthesis ofα,β-dehydroamino acids and their peptides was developed.Proline efficiently catalyzed an aldol condensation reaction of a glycine Schiff base with a variety of aldehydes.The hy...A general protocol for the synthesis ofα,β-dehydroamino acids and their peptides was developed.Proline efficiently catalyzed an aldol condensation reaction of a glycine Schiff base with a variety of aldehydes.The hydroxy group on the benzophenone imine was crucial for high Z/E selectivity and further transimination for protecting group-freeα,β-dehydroamino esters.Peptide elongation of both the C-and N-terminals highlighted the usefulness of our present protocol.展开更多
The following article has been retracted due to the investigation of complaints received against it. The Editorial Board found that the paper has been submitted to other journals at the same time. The scientific commu...The following article has been retracted due to the investigation of complaints received against it. The Editorial Board found that the paper has been submitted to other journals at the same time. The scientific community takes a very strong view on this matter, and the International Journal of Organic Chemistry treats all unethical behavior seriously. This paper published in Vol. 2 No.2 166-171, 2012, has been removed from this site.展开更多
This article reports on the synthesis of acrylate monomer from renewable material. Vanillin was selected to be the start material to produce new monomer called vanillin acrylate and abbreviated by (VA). It has been su...This article reports on the synthesis of acrylate monomer from renewable material. Vanillin was selected to be the start material to produce new monomer called vanillin acrylate and abbreviated by (VA). It has been successfully investigated by 1H, 13C NMR, IR and UV and all results were in logic state. The next step was to synthetize three different thermo-responsive functional copolymers by incorporation of three different molar ratios of vanillin acrylate (10, 20, 30 mol%) with N-Isopropylacrylamide via free radical polymerization by AIBN as initiator in solution. All copolymers were deduced by 1NMR and IR and all showed the presence of aldehyde group. The copolymer was used for grafting of tryptophan and β-alanine through the chemical link between amino group and the active aldehyde group by click reactions to form Schiff’s base imine compounds. Moreover, polymers were also elucidated by 1HNMR, IR and UV, Size Exclusion Chromatography (SEC) was used for the molecular weight determination, differential scanning calorimeter (DSC) for glass temperature of solid polymers, XRD for crystallinity. UV-vis Spectroscopy was used for the determination of phase separation or the lower critical solution temperature (Tc) of polymers solution not only in deionized water but in pH5 and pH11. The mount of conversation and linked amino acid was determined by UV-vis Spectroscopy.展开更多
A complete study of the asymmetric addition of phenylacetylene to ketones catalyzed by Schiff-base amino alcohol-Zn complex is reported in this article. The Schiff-base amino alcohols were easily prepared from amino a...A complete study of the asymmetric addition of phenylacetylene to ketones catalyzed by Schiff-base amino alcohol-Zn complex is reported in this article. The Schiff-base amino alcohols were easily prepared from amino acids in three steps. When the amount of ligand was 1%(molar fraction), an e.e. value up to 94% was obtained. A series of practical chiral ligands were applied in the enantioselective addition of phenylacetylene to ketones without adding another stronger Lewis acid except zinc.展开更多
文摘In this study, we exhibited an amino acid (arginine and threonine) derivative Schiff base copper(II) complexes incorporating an azobenzene moiety as a photoresponsive site and conjugated it to egg white lysozyme, a well-known protein, to change ligand conformation under binding to lysozyme. Among several spectroscopic investigations, ESR clearly showed that the nitrogen atom of the amino acid residue of lysozyme was bound to the paramagnetic copper(II) ion of the complex, and UV light irradiation confirmed photoisomerization of the azobenzene moiety of the ligand to cis-form. The binding mode was considered by means of spectroscopic as well as computational methods, whereas complete crystallographic verification was still a preliminary stage.
文摘The dependence of electronic absorption spectra antimicrobial property on the substituent position was investigated using three Schiff bases derived from salicylaldehyde and isomeric aminobenzoic acids in three solvents of different polarities. The absorption maxima in all three solvents exhibited dependence on the position of substituent with the absorption maxima undergoing a red shift as solvent polarity increased. The in vitro antibacterial activity of the compounds against some clinically important bacteria namely Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853), Staphylococcus aureus (ATCC 25923), Enterococcus feacalis (ATCC 29212) was determined in N,N”-dimethylformamide and 1,4-dioxane using the agar dilution method. The results revealed that the ortho and meta substituted Schiff bases exhibited better antimicrobial activity in the non-polar solvent.
文摘Four Schiff bases, from pyruvic acid (1) with amines containing N and S donor atoms, thiocarbohydrazide (2, 61%), 2-methyl-3-thiosemicarbazide (3, 26%), S-benzyldithiocarbazate (4, 51%) and S-n-octyldithiocarbazate (5, 63%) have been successfully synthesized. The conventional method was used and a series of novel linear and cyclic Schiff bases were obtained with or without catalyst. All the Schiff bases were fully characterized by CHN elemental analysis, FT-IR, 1H & 13C NMR, EI-MS and two of the Schiff bases were further characterized by X-ray crystallographic structure analysis. Compound 2 crystallizes in the triclinic space group P-1 and unit cell dimensions are: a = 4.1777(8), b = 5.9538(11), c = 13.458(3) Å, α = 92.759(6), β = 90.813(6), γ = 100.040(6)°, R1 = 0.0439. Compound 3 crystallizes in the orthorhombic space group P n a 2(1) and unit cell dimensions are: a = 5.5992(2), b = 11.3962(5), c = 10.6473(5), α = 92.759(6), β = 90.813(6), γ = 100.040(6)°, R1 = 0.0285. Compounds 2 and 3 were obtained as cyclic Schiff bases which are triazine derivatives.
文摘Glutamic acid-salicylaldehyde Schiff-base metal complexes are bound into bovine serum albumin (BSA), which afforded BSA binding Schiff-base metal complexes (BSA-SalGluM, M=Cu, Co, Ni, Zn). The BSA binding metal complexes were characterized by UV-vis spectra and Native PAGE. It showed that the protein structures of BSA kept after coordinating amino acid Schiff-bases metal complexes. The effect of the antioxidant activity was investigated. The results indicate that the antioxidant capacity of BSA increased more than 10 times after binding Schiff-base metal complexes.
文摘Six new complexes of lanthanum with amino acid Schiff base ligands, A-F, were prepared in methanol-aqueous solution. The composition and properties of the title complexes were characterized by elemental analysis, molar conductance, infrared, electronic spectra, H-1 NMR, thermogravimetric and differential thermal analysis.
文摘Seven heterobinuclear complexes of Cu-Ln with N, N'-bis(3-carboxylsali cylidene) ethylenediamine(ES) were synthesized and characterized by elemental analysis, molar conductivity, thermogravimetry, IR and electronic spectra. The room temperature magnetic moments show that there are basically no spin exchange interactions between the ions of Cu2+ and Ln(3+) in the CuLnESCl . nH(2)O compounds.
文摘Condensation of eqqimolar quantities of salicylaldehyde and a-amino acid (glycine, alanine, valine, leucine, Phenylalanine, serine, cysteine) in absolute Methanol-KOH gives the amino acid Schiff base[1]. Its germanium tetrachloride adducts of the type GeCL. (sal=aa.k)2 have been prepared in absolute mothanol[2]and characterized by elemental analyses, conductance measurements, IR and 1H-NMR spectra, electronic spectra, cyclic voltammetry and thermal analyses. etc.
基金This work was supported by the Natural Science Foundation of Hunan Province (No. 05JJ30016) and Science Foundation of Hengyang Normal University of China (2005A01), the Basic Research of the Hunan Province (03JZY3036)
文摘The title complex [Zn(L)(phen)(CH3OH)] (L = C8H6BrO4NS, aminomethanesulfonic acid 5-bromo-salicylaldelyde schiff base; phen = 1,10-phenanthroline) has been synthesized and characterized by X-ray diffraction method. The crystal belongs to monoclinic, space group P21/c with a = 1.8712(3), b = 1.38008(19), c = 0.83685(12) nm, β = 97.791 (2)°, Mr = 569.72, V = 2.1411 (5) nm^3, Z= 4, Dc = 1.767 g/cm^3,μ = 3.151 mm^-1, F(000) = 1144, the final R = 0.0402 and wR = 0.0885. The central Zn(Ⅱ) is six-coordinated by one nitrogen and two oxygen atoms from the Schiff base, two nitrogen atoms from 1,10-phenanthroline and one oxygen from methanol to form a distorted octahedral coordination geometry.
基金Project(76132020) supported by the Post-Doctoral Science Fund of Central South University
文摘The amino acid Schiff base complex (Sal-AMBA-Mn) was prepared with p-amino-methylbenzoic acid, salicylaldehyde and Mn(OAc)2·4H2O. Its structures was characterized with IR and UV spectra. Oxygenation mechanism of the complex in N, N-dimethylformamide solution was investigated. The results show that lower temperature is in favor of the oxygenation, and energy, enthalpy and entropy are -3.8 kJ/mol, -4.2 J/mol and -161.44 J/(mol·K), respectively. In the presence of the manganese complex, dehydroepiandrosterone acetate is effectively oxidized by molecular oxygen and the corresponding enone 7-ketodehydroepiandrosterone acetate is obtained. The yield is 62.1% when the oxidation is carried out under the reaction conditions of 60 ℃, 2 MPa of O2 pressure, C5H5N as a solvent and molar ratio of the substrate to the complex of 1:10.
文摘New dibutyltin(IV) complexes of Schiff base derived from 5-chloroindoline-2,3-dione, indoline- 2,3-dione with amino acids (tryptophan, alanine and valine) were synthesized and characterized by elemental analysis, IR, electronic spectra, conductance measurements, and biological activity. The analytical data showed that the Schiff base ligand acts as bidentate towards metal ions via the azomethine nitrogen and carboxylate oxygen by a stoichiometric reaction of M:L (1:2) to form metal complexes. NMR (1H, 13C and 119Sn) spectral data of the ligands and metal complex agree with proposed structures. The conductivity values between 14 - 27 ohm-1cm2mol-1 in DMF imply the presence of non-electrolyte species. 3D molecular modeling and analysis of bond lengths and bond angles have also been conducted for a representative compound, [Bu2Sn(L2)2], to substantiate the proposed structures. Antibacterial results indicate that the metal complexes are more active than the free ligands.
基金supported by MEXT KAKENHI grant numbers JP21A204,JP21H05207,and JP21H05208 for The Grant-in-Aid for Transformative Research Areas(A)Digitalization-driven Transformative Organic Synthesis(Digi-TOS)from MEXT,a Grant-in-Aid for Scientific Research(B)(JP21H02607)the JST-FOREST program(JPMJFR2229)+1 种基金a Grant-in-Aid for Basis for Supporting Innovative Drug Discovery and Life Science Research(BINDS)(JP20am0101091,JP22ama121031)and AMED(JP21ak0101167,JP22ak0101167,JP23ak0101167)J.S.thanks the Japan Science and Technology Agency(JST)SPRING(JPMJSP2136).
文摘A general protocol for the synthesis ofα,β-dehydroamino acids and their peptides was developed.Proline efficiently catalyzed an aldol condensation reaction of a glycine Schiff base with a variety of aldehydes.The hydroxy group on the benzophenone imine was crucial for high Z/E selectivity and further transimination for protecting group-freeα,β-dehydroamino esters.Peptide elongation of both the C-and N-terminals highlighted the usefulness of our present protocol.
文摘The following article has been retracted due to the investigation of complaints received against it. The Editorial Board found that the paper has been submitted to other journals at the same time. The scientific community takes a very strong view on this matter, and the International Journal of Organic Chemistry treats all unethical behavior seriously. This paper published in Vol. 2 No.2 166-171, 2012, has been removed from this site.
文摘This article reports on the synthesis of acrylate monomer from renewable material. Vanillin was selected to be the start material to produce new monomer called vanillin acrylate and abbreviated by (VA). It has been successfully investigated by 1H, 13C NMR, IR and UV and all results were in logic state. The next step was to synthetize three different thermo-responsive functional copolymers by incorporation of three different molar ratios of vanillin acrylate (10, 20, 30 mol%) with N-Isopropylacrylamide via free radical polymerization by AIBN as initiator in solution. All copolymers were deduced by 1NMR and IR and all showed the presence of aldehyde group. The copolymer was used for grafting of tryptophan and β-alanine through the chemical link between amino group and the active aldehyde group by click reactions to form Schiff’s base imine compounds. Moreover, polymers were also elucidated by 1HNMR, IR and UV, Size Exclusion Chromatography (SEC) was used for the molecular weight determination, differential scanning calorimeter (DSC) for glass temperature of solid polymers, XRD for crystallinity. UV-vis Spectroscopy was used for the determination of phase separation or the lower critical solution temperature (Tc) of polymers solution not only in deionized water but in pH5 and pH11. The mount of conversation and linked amino acid was determined by UV-vis Spectroscopy.
基金the National Natural Science Foundation of China(Nos.20472026 and 20525206)Chang Jiang Scholar Program of the Ministry of Education, China.
文摘A complete study of the asymmetric addition of phenylacetylene to ketones catalyzed by Schiff-base amino alcohol-Zn complex is reported in this article. The Schiff-base amino alcohols were easily prepared from amino acids in three steps. When the amount of ligand was 1%(molar fraction), an e.e. value up to 94% was obtained. A series of practical chiral ligands were applied in the enantioselective addition of phenylacetylene to ketones without adding another stronger Lewis acid except zinc.