Salicylaldehyde-2-(4-isobutylphenyl)-propionyl hydrazone Schiff base(H2L) has been synthesized and characterized by elemental analysis,IR,1H-NMR spectrum and single-crystal X-ray diffraction.Single-crystal X-ray d...Salicylaldehyde-2-(4-isobutylphenyl)-propionyl hydrazone Schiff base(H2L) has been synthesized and characterized by elemental analysis,IR,1H-NMR spectrum and single-crystal X-ray diffraction.Single-crystal X-ray diffraction analysis showed that H2L is of monoclinic system,space group P21/c with a = 5.6844(5),b = 33.568(3),c = 9.6959(9) ,β = 91.758(2)°,V = 1849.2(3) 3,Mr = 324.41,F(000) = 696,Z = 4,Dc = 1.165 g/cm3,μ = 0.076 mm-1,R = 0.0448 and wR = 0.1221.In the solid form,the strong intramolecular hydrogen bonds make H2L fully extended into an E isomer about the N=N bond,and each molecule interacts with two neighbors to form 1D hydrogen-bonded chains.The Schiff base presents two different sets of signals in the 1H-NMR and 13C-NMR spectra in either chloroform or dimethylsulfoxide solution,showing the presence of both E and Z isomers.展开更多
Three new kinds of acylhydrazone compounds (C12H10FN5O?H2O, 1; C12H10ClN5O?2CH3COOH, 2; C12H10BrN5O, 3) were synthesized by the reaction of 2-amino-3- pyrazinecarbohydrazide (C5H7N5O) with halogenated benzaldehy...Three new kinds of acylhydrazone compounds (C12H10FN5O?H2O, 1; C12H10ClN5O?2CH3COOH, 2; C12H10BrN5O, 3) were synthesized by the reaction of 2-amino-3- pyrazinecarbohydrazide (C5H7N5O) with halogenated benzaldehyde (C7H5OX, X = F, Cl, Br). The structures of the three compounds were characterized by elemental analysis, 1H NMR, IR and X-ray diffraction. X-ray single-crystal diffraction presents that the three compounds all belong to triclinic system, P space group. Thermal gravity analyses show that three compounds have excellent thermal stabilities and all the thermal decomposition temperature of maximum weight loss was around 300 °C. The interactions of the compounds with CT-DNA were investigated by UV-Vis spectrum, fluorescence spectrum and viscosity measurement. All the results suggest that three compounds could bind with CT-DNA through intercalation. The fluorescence spectrum was also used to study the interactions of three compounds with BSA. It was proved that all the compounds could quench the intrinsic fluorescence of BSA via a static quenching process. Compound 2 displays the strongest binding ability both in the reaction with CT-DNA or BSA. Antimicrobial test was carried on Escherichia coli, Staphylococcus aureus and Salmonella, and 2 is more effective against S. aureus. But in MTT assay, 1 shows better cytotoxity activity against A549 cells.展开更多
The title organometallic compounds were synthesized by the condensation of formyl and acetyl ferrocene with cyanoacetyl, propionyl, butyryl, o furoyl, o thiofuroyl and m pyridinecarboxy hydrazine in anh...The title organometallic compounds were synthesized by the condensation of formyl and acetyl ferrocene with cyanoacetyl, propionyl, butyryl, o furoyl, o thiofuroyl and m pyridinecarboxy hydrazine in anhydrous ethanol under reflux. The IR, 1H NMR, MS, and Mssbauer spectra for these compounds were recorded and are discussed.展开更多
The reactivity and stability of seventeen (17) imidazo [1,2-a]pyridine N-acylhydrazone derivatives were investigated using density functional theory at the B3LYP/6-31+ G (d, p) level. Analysis of the molecular electro...The reactivity and stability of seventeen (17) imidazo [1,2-a]pyridine N-acylhydrazone derivatives were investigated using density functional theory at the B3LYP/6-31+ G (d, p) level. Analysis of the molecular electrostatic potential (MEP) and determination of the dual descriptor revealed that in most cases, the nitrogen atoms of the 6-πelectron conjugation, the oxygen, and the sulfur atom are nucleophilic site. Chemical reactivity of the compounds was assessed through analysis of frontier molecular orbitals (HOMO and LUMO), energy gap (Δℰ), chemical hardness (η), and the softness (S). Consequently, the compound 9e exhibited the lowest reactivity, least electron donating, and the highest stability. This comprehensive study offers valuable insights into the chemical behavior of these derivatives, crucial for further exploration and potential applications.展开更多
An acid-sensitive delivery system based on acylhydrazone bond was developed for high loading and efficient delivery of doxorubicin.Doxorubicin(DOX)was covalently combined with dihydrazide adipate to form acid-sensitiv...An acid-sensitive delivery system based on acylhydrazone bond was developed for high loading and efficient delivery of doxorubicin.Doxorubicin(DOX)was covalently combined with dihydrazide adipate to form acid-sensitive hydrazone bond based on Schiff base reaction,then the intermediate was covalently combined with carboxymethyl chitosan through amide bond to form polymeric prodrugs,and nanoparticles were formed through self-assembling.Moreover,the structural and particle properties of CMCS-ADH-DOX were characterized by ultraviolet visible near infrared spectrophotometry(UV),nuclear magnetic resonance spectroscopy(^(1)H-NMR),fourier transform infrared spectroscopy(FT-IR),dynamic light scattering(DLS),and transmission electron microscopy(TEM).The mean diameter of the self-assembled nanoparticles is 165 nm,while the morphology is a relatively uniform spherical shape.Moreover,these DOXloaded nanoparticles showed pH-triggered drug release behavior.Compared with free DOX,CAD NPs showed lower toxic side effects in L929 cells and similar toxicity in 4T1 cells.The experimental results indicate that the CMCS-ADH-DOX nanoparticles may be used as an acid-sensitive targeted delivery system with good application prospect for cancer.展开更多
Four new acylhydrazones containing carboxyl,3a3d,were synthesized and their compositions and structures were characterized with elemental analysis, MS,IR and 1H NMR spectra.Their bacterio-(static) activities against...Four new acylhydrazones containing carboxyl,3a3d,were synthesized and their compositions and structures were characterized with elemental analysis, MS,IR and 1H NMR spectra.Their bacterio-(static) activities against staphylocus auteus,escherichia coil and bacillus subtilis were studied by Kirby-Bauer method.展开更多
基金supported by the Natural Science Foundation of Hubei Province (No.2008CDA067)South-central University for Nationalities Foundation (No.YZZ08014)
文摘Salicylaldehyde-2-(4-isobutylphenyl)-propionyl hydrazone Schiff base(H2L) has been synthesized and characterized by elemental analysis,IR,1H-NMR spectrum and single-crystal X-ray diffraction.Single-crystal X-ray diffraction analysis showed that H2L is of monoclinic system,space group P21/c with a = 5.6844(5),b = 33.568(3),c = 9.6959(9) ,β = 91.758(2)°,V = 1849.2(3) 3,Mr = 324.41,F(000) = 696,Z = 4,Dc = 1.165 g/cm3,μ = 0.076 mm-1,R = 0.0448 and wR = 0.1221.In the solid form,the strong intramolecular hydrogen bonds make H2L fully extended into an E isomer about the N=N bond,and each molecule interacts with two neighbors to form 1D hydrogen-bonded chains.The Schiff base presents two different sets of signals in the 1H-NMR and 13C-NMR spectra in either chloroform or dimethylsulfoxide solution,showing the presence of both E and Z isomers.
基金supported by the National Natural Science Foundation of China(Nos.21073139,21103135 and 21301139)
文摘Three new kinds of acylhydrazone compounds (C12H10FN5O?H2O, 1; C12H10ClN5O?2CH3COOH, 2; C12H10BrN5O, 3) were synthesized by the reaction of 2-amino-3- pyrazinecarbohydrazide (C5H7N5O) with halogenated benzaldehyde (C7H5OX, X = F, Cl, Br). The structures of the three compounds were characterized by elemental analysis, 1H NMR, IR and X-ray diffraction. X-ray single-crystal diffraction presents that the three compounds all belong to triclinic system, P space group. Thermal gravity analyses show that three compounds have excellent thermal stabilities and all the thermal decomposition temperature of maximum weight loss was around 300 °C. The interactions of the compounds with CT-DNA were investigated by UV-Vis spectrum, fluorescence spectrum and viscosity measurement. All the results suggest that three compounds could bind with CT-DNA through intercalation. The fluorescence spectrum was also used to study the interactions of three compounds with BSA. It was proved that all the compounds could quench the intrinsic fluorescence of BSA via a static quenching process. Compound 2 displays the strongest binding ability both in the reaction with CT-DNA or BSA. Antimicrobial test was carried on Escherichia coli, Staphylococcus aureus and Salmonella, and 2 is more effective against S. aureus. But in MTT assay, 1 shows better cytotoxity activity against A549 cells.
文摘The title organometallic compounds were synthesized by the condensation of formyl and acetyl ferrocene with cyanoacetyl, propionyl, butyryl, o furoyl, o thiofuroyl and m pyridinecarboxy hydrazine in anhydrous ethanol under reflux. The IR, 1H NMR, MS, and Mssbauer spectra for these compounds were recorded and are discussed.
文摘The reactivity and stability of seventeen (17) imidazo [1,2-a]pyridine N-acylhydrazone derivatives were investigated using density functional theory at the B3LYP/6-31+ G (d, p) level. Analysis of the molecular electrostatic potential (MEP) and determination of the dual descriptor revealed that in most cases, the nitrogen atoms of the 6-πelectron conjugation, the oxygen, and the sulfur atom are nucleophilic site. Chemical reactivity of the compounds was assessed through analysis of frontier molecular orbitals (HOMO and LUMO), energy gap (Δℰ), chemical hardness (η), and the softness (S). Consequently, the compound 9e exhibited the lowest reactivity, least electron donating, and the highest stability. This comprehensive study offers valuable insights into the chemical behavior of these derivatives, crucial for further exploration and potential applications.
基金Funded by the Industrial Technology Research Institute of Hubei Provincial Department of Science and Technology(No.2020DEB012)the Hubei Provincial Department of Science and Technology Support Enterprise Technology Innovation Development Project(No.2021BAB119)。
文摘An acid-sensitive delivery system based on acylhydrazone bond was developed for high loading and efficient delivery of doxorubicin.Doxorubicin(DOX)was covalently combined with dihydrazide adipate to form acid-sensitive hydrazone bond based on Schiff base reaction,then the intermediate was covalently combined with carboxymethyl chitosan through amide bond to form polymeric prodrugs,and nanoparticles were formed through self-assembling.Moreover,the structural and particle properties of CMCS-ADH-DOX were characterized by ultraviolet visible near infrared spectrophotometry(UV),nuclear magnetic resonance spectroscopy(^(1)H-NMR),fourier transform infrared spectroscopy(FT-IR),dynamic light scattering(DLS),and transmission electron microscopy(TEM).The mean diameter of the self-assembled nanoparticles is 165 nm,while the morphology is a relatively uniform spherical shape.Moreover,these DOXloaded nanoparticles showed pH-triggered drug release behavior.Compared with free DOX,CAD NPs showed lower toxic side effects in L929 cells and similar toxicity in 4T1 cells.The experimental results indicate that the CMCS-ADH-DOX nanoparticles may be used as an acid-sensitive targeted delivery system with good application prospect for cancer.
文摘Four new acylhydrazones containing carboxyl,3a3d,were synthesized and their compositions and structures were characterized with elemental analysis, MS,IR and 1H NMR spectra.Their bacterio-(static) activities against staphylocus auteus,escherichia coil and bacillus subtilis were studied by Kirby-Bauer method.