553-53-7Relevant academic research and scientific papers
Synthesis, characterization and computational studies of 4-[(Pyridine-3-carbonyl)-hydrazonomethyl]-benzoic acid
Elif ?ztürkkan ?zbek, Füreya,Kalay, Erbay,Necefo?lu, Hacali,U?urlu, Güventürk
, (2020)
A new hydrazone derivative compound, 4-[(Pyridine-3-carbonyl)-hydrazonomethyl]-benzoic acid, C15H11N3O, was obtained and characterized by 1H NMR, 13C NMR and UV–Vis, FT-IR and FT-Raman spectroscopy techniques. Molecular geometry, vibrational wavenumbers, frontier molecular orbital and non-linear optical (NLO) property of the title compound were calculated using ab initio Hartree-Fock (HF) and Density Functional Theory (DFT), employing B3LYP functional at 6–311++G (d,p) basis set. 1H and 13C NMR chemical shifts were calculated by using the gauge in dependent atomic orbital (GIAO) method at the HF and B3LYP methods with different basis sets. In addition, the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) were obtained from DFT LSDA methods with 6–311++G (d,p) basis set. The NLO behaviour of the title compound has been studied by determining the electric dipole moment (μ) and hyperpolarizability (β) using both B3LYP/6–311++G (d,p) and HF/6–311++G (d,p) methods. The energy gaps s(ΔEgap=ELUMO?EHOMO) of title molecule were calculated at 4.15, 2.77 and 9.81 eV with DFT-B3LYP/6–311++ G (d,p), DFT-LSDA/6–311++ G (d,p) and HF/6–311++ G (d,p) level of theory, respectively. The calculated experimentally energy gap was found as 2.827 eV.
A novel coumarin-based fluorescence chemosensor for Al3+ and its application in cell imaging
Zhu, Guohua,Huang, Yang,Wang, Chun,Lu, Linxia,Sun, Tongming,Wang, Miao,Tang, Yanfeng,Shan, Doudou,Wen, Shuijin,Zhu, Jinli
, p. 105 - 110 (2019)
As an efficient turn-on fluorescent chemosensor for Al3+, a new coumarin derivative (CND) has been designed and synthesized by the condensation of 8-formyl-7-hydroxycoumarin with niacin hydrazide. The spectroscopic studies revealed that the sensor CND exhibited a remarkable fluorescence enhancement towards Al3+ with high selectivity and sensitivity in EtOH-HEPES (95:5, v/v, pH = 7.40), which was attributed to the photoinduced electron transfer (PET) and –C[dbnd]N isomerization mechanism. Fluorescence titration calculations data showed that the detection limit and the association constants of CND for Al3+ were found to be 2.51 × 10?7 M and 9.64 × 104 M?1, respectively. The results of experiments, including Job's plot, 1H NMR titration and ESI-MS, revealed that the stoichiometric binding between CND and Al3+ was 1:1. The investigations of the pH dependency of CND for Al3+ detection, and the cell imaging suggested the sensor CND could be promisingly applied for the recognition of Al3+ in biological cells.
Theoretical and experimental assesment of structural, spectroscopic, electronic and nonlinear optical properties of two aroylhydrazone derivative
?ztürkkan ?zbek, Füreya Elif,H?kelek, Tuncer,Kalay, Erbay,Necefo?lu, Hacali,U?urlu, Güventürk
, (2021)
Two aroylhydrazone, N'-(pyridine-4-ylmethylene)nicotic acid hydrazide (1) and N'-(pyridine-3-ylmethylene)nicotic acid hydrazide (2), were synthesized and their structures were determined by single-crystal X-ray diffraction analysis. The X-ray analysis indicated that the compound 1 was crystallized in triclinic crystal system with P -1space group a = 8.7899 (2) ?, b = 10.8983 (3) ?, c = 11.7726 (3) ?, α= 89.952 (3)°, β = 88.684 (3)°, γ= 75.293 (2)°, V = 1090.50 (5) ?3 and Z = 4 and compound 2 was crystallized in monoclinic crystal system with P21/c space group, a = 11.9239 (3) ?, b = 8.6495 (2) ?, c = 11.1021 (3) ?, α= 90 (3)°, β = 111.664 (3) (3)°, γ= 90°, V = 1064.14 (5) ?3 and Z = 4. Intermolecular interactions of the compounds were determined by Hirhfeld Surface Analysis. The H ··· H interactions with 37.9percent (for compound 1) and 37.5percent (for compound 2) contributions are the most important interactions to the overall crystal packings. FT-IR, Raman, 1H and 13C NMR and UV–Vis spectroscopy methods were used for spectroscopic characterization of the compounds. The spectroscopic properties of the compounds were calculated theoretically by using Density Functional Theory (DFT) with B3LYP and ab initio Hartree-Fock (HF) methods at different basis sets. A correlation was found between the theoretical and experimental values for the spectroscopic results. Moreover, the highest occupied molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO), electric dipole moment (μ), polarizability (α) and hyperpolarizability (β) of the compounds were computed both DFT/B3LYP/6–311++G(d,p) and ab initio HF/6–311++G(d,p) methods. The calculated first hyperpolarizability value at the DFT/B3LYP/6–31++G (d,p) level of compound 1 with dimer structure is 18.14 times larger than urea, the standard nonlinear optical material. So, this value implies that compound 1 considered have potential candidates for designing high quality nonlinear optical materials. The energy gap (ΔEgap) and Molecular Electrostatic Potential (MEP) of the compounds were investigated. The structural and vibration frequency values calculated theoretically were compared with the experimental values.
New heterocyclic Schiff base-metal complex: Synthesis, characterization, density functional theory study, and antimicrobial evaluation
Hashem, Heba E.,Mohamed, Eslam A.,Farag, Ahmed A.,Negm, Nabel A.,Azmy, Eman A. M.
, (2021)
A new series of heterocyclic Schiff base complexes derived from the condensation of nicotinohydrazide with different heterocyclic aldehyde, followed by metalation with Co (II) and Cu (II) metal ions. The chemical structures of the synthesized compounds have been characterized by elemental analysis, Fourier transform infrared spectroscopy, proton nuclear magnetic resonance, ultraviolet–visible spectroscopy, and magnetic susceptibility. The spectral and magnetic data confirmed their chemical structures, furthermore, the geometry of Cu (II) and Co (II) complexes were square-planar or distorted tetrahedral. X-ray diffraction measurements supported the crystalline structures of the metal complexes rather than the amorphous form of the parent Schiff bases. Thermogravimetric analysis revealed the upgrading of the thermal stability of metal complexes compared to their Schiff base ligands. Antimicrobial efficacies of the Schiff base ligands and their corresponded metal complexes were screened against Staphylococcus aureus and Bacillus subtilis as Gram-positive bacteria, Escherichia coli, and Proteus vulgaris as Gram-negative bacteria, and fungi Aspergillus flavus, Candida albicans. The antimicrobial inhibitory data revealed higher antimicrobial activities of metal complexes compared to their Schiff base ligands. Density functional theory module by Gaussian 09 W software proved the chemical reactivity of the prepared Schiff base ligands based on the total energy, energy gap, EHOMO, and ELUMO energies.
Synthesis, structural, spectroscopic, and thermal studies of some transition-metal complexes of a ligand containing the amino mercapto triazole moiety
El-Nahas, Ahmed M.,Emam, Sanaa M.,Tolan, Dina A.
, (2020)
A new series of transition-metal complexes of Schiff base ligand containing the amino mercapto triazole moiety (HL) was prepared. The Schiff base and its metal complexes were elucidated by different spectroscopic techniques (infrared [IR], 1H nuclear magnetic resonance, UV–Visible, mass, and electron spin resonance [ESR]), and magnetic moment and thermal studies. Quantum chemical calculations have been carried out to study the structure of the ligand and some of its complexes. The IR spectra showed that the ligand is chelated with the metal ion in a neutral, tridentate, and bidentate manner using NOS and NO donors in complexes 1–6, 10–12, and 7 and 8, respectively, whereas it behaves in a monobasic tridentate fashion using NOS donor sites in copper(II) nitrate complex (9). The magnetic moment and electronic spectra data revealed octahedral and square pyramidal geometries for complexes 2, 11, 12, and 5–8 and 10, respectively. However, the other complexes were found to have tetrahedral (4), trigonal bipyramidal (1 and 3), and square planar (9) structures. Thermal studies revealed that the chelates with different crystallized solvents undergo different types of interactions and the decomposition pathway ended with the formation of metal oxygen (MO) and metal sulfur (MS) as final products. The ESR spectrum of copper(II) complex 10 is axial in nature with hyperfine splitting with 2B1g as a ground state. By contrast, complexes 7 and 8 undergo distortion around the Cu(II) center, affording rhombic ESR spectra. The HL ligand and some of its complexes were screened against two bacterial species. Data showed that complex 12 demonstrated a better antibacterial activity than HL ligand and other chelates.
Design, docking, synthesis, and characterization of novel N'(2-phenoxyacetyl) nicotinohydrazide and N'(2-phenoxyacetyl)isonicotinohydrazide derivatives as anti-inflammatory and analgesic agents
Al-Ostoot, Fares Hezam,Khanum, Shaukath Ara,M, Pallavi H,Vivek, Hamse Kameshwar
, (2021/09/14)
Inflammation is the complex biological response of vascular tissues, which is partly determined by prostaglandins (PLA2). The cyclooxygenase (COX) enzyme exists in two isoforms: COX-1 and COX-2 and by the action of this, the PGs are produced. Besides, nonsteroidal anti-inflammatory drugs (NSAIDs) are therapeutic agents useful in the treatment of inflammation. Encouraged by this, the new derivatives of N'(2-phenoxyacetyl)nicotinohydrazide 9(a-e) and N'(2-phenoxyacetyl)isonicotinohydrazide 10(a-e) were designed, synthesized, characterized, and identified as remarkable anti-inflammatory and analgesic agents. These compounds were prepared in a series of steps starting with different phenol derivatives. Among the series, compound (10e) showed the highest IC50 value for COX-1 inhibition, whereas compounds (9e) and (10e) exhibited the highest COX-2SI. Further, molecular Docking Studies have been performed for the potent compound to check the three-dimensional geometrical view of the ligand binding to the targeted enzymes.
Pleuromutilin derivative with 1, 3, 4-oxadiazole side chain and preparation and application thereof
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Paragraph 0055-0056; 0070; 0090; 0093; 0095; 0102, (2021/07/24)
The invention belongs to the field of medicinal chemistry, and particularly relates to a pleuromutilin derivative with a 1, 3, 4-oxadiazole side chain and preparation and application thereof The pleuromutilin derivative with the 1, 3, 4-oxadiazole side chain is a compound shown in a formula 2 or a pharmaceutically acceptable salt thereof, and a solvent compound, an enantiomer, a diastereoisomer and a tautomer of the compound shown in the formula 2 or the pharmaceutically acceptable salt thereof or a mixture of the solvent compound, the enantiomer, the diastereoisomer and the tautomer in any proportion, including a racemic mixture. The pleuromutilin derivative has good antibacterial activity, is especially suitable for being used as a novel antibacterial agent for systemic system infection of animals or human beings, and has good water solubility.
Design, synthesis, in vitro and in vivo evaluation against MRSA and molecular docking studies of novel pleuromutilin derivatives bearing 1, 3, 4-oxadiazole linker
Liu, Jie,Zhang, Guang-Yu,Zhang, Zhe,Li, Bo,Chai, Fei,Wang, Qi,Zhou, Zi-Dan,Xu, Ling-Ling,Wang, Shou-Kai,Jin, Zhen,Tang, You-Zhi
, (2021/05/17)
A class of pleuromutilin derivatives containing 1, 3, 4-oxadiazole were designed and synthesized as potential antibacterial agents against Methicillin-resistant staphylococcus aureus (MRSA). The ultrasound-assisted reaction was proposed as a green chemistry method to synthesize 1, 3, 4-oxadiazole derivatives (intermediates 85–110). Among these pleuromutilin derivatives, compound 133 was found to be the strongest antibacterial derivative against MRSA (MIC = 0.125 μg/mL). Furthermore, the result of the time-kill curves displayed that compound 133 could inhibit the growth of MRSA in vitro quickly (- 4.36 log10 CFU/mL reduction). Then, compound 133 (- 1.82 log10 CFU/mL) displayed superior in vivo antibacterial efficacy than tiamulin (- 0.82 log10 CFU/mL) in reducing MRSA load in mice thigh model. Besides, compound 133 exhibited low cytotoxicity to RAW 264.7 cells. Molecular docking studies revealed that compound 133 was successfully localized in the binding pocket of 50S ribosomal subunit (ΔGb = -10.50 kcal/mol). The results indicated that these pleuromutilin derivatives containing 1, 3, 4-oxadiazole might be further developed into novel antibiotics against MRSA.
Design and synthesis of novel furan, furo[2,3-d]pyrimidine and furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives as potential VEGFR-2 inhibitors
Abd El-Mageed, Menna M.A.,Eissa, Amal A.M.,Farag, Awatef El-Said,Osman, Essam Eldin A.
, (2021/09/15)
Novel furan 6a-c, furo[2,3-d]pyrimidine 7a-f, 9, 10a-f, 12a,b, 14a-d and furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine 8a-f derivatives were designed based on their structural similarity to a previously described oxazole VEGFR-2 back pocket binding fragment. The designed compounds were synthesized and screened for their in vitro VEGFR-2 inhibitory activity where they exhibited good to moderate nanomolar inhibition with improved ligand efficiencies. 8b and 10c (IC50 = 38.72 ± 1.7 and 41.40 ± 1.8 nM, respectively) were equipotent to sorafenib and 6a, 6c, 7f, 8a, 8c, 10b, 10f, 12b, 14c and 14d showed good activity (IC50 = 43.31–98.31 nM). The furotriazolopyrimidines 8a-c and furopyrimidine derivative 10c were further evaluated for their in vitro antiproliferative activity against human umbilical vein endothelial cells (HUVECs) where 8b showed higher potency than sorafenib and resulted in cell cycle arrest at G2/M phase whereas 8c revealed good antiproliferative activity with cell cycle arrest at G1 phase. Moreover, 8a-c and 10c showed significant inhibitory effects on the invasion and migration of HUVECs. Molecular docking study was conducted to gain insight about the potential binding mode. The furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives 8b and 8c represent interesting starting point for antiangiogenic compounds based on their activity and favorable drug likeness profiles.
Development of Novel (+)-Nootkatone Thioethers Containing 1,3,4-Oxadiazole/Thiadiazole Moieties as Insecticide Candidates against Three Species of Insect Pests
Cheng, Wanqing,Fan, Jiangping,Guo, Yong,Han, Meiyue,Ma, Nannan,Yan, Xiaoting,Yang, Ruige
, p. 15544 - 15553 (2022/01/03)
To improve the insecticidal activity of (+)-nootkatone, a series of 42 (+)-nootkatone thioethers containing 1,3,4-oxadiazole/thiadiazole moieties were prepared to evaluate their insecticidal activities against Mythimna separata Walker, Myzus persicae Sulzer, and Plutella xylostella Linnaeus. Insecticidal evaluation revealed that most of the title derivatives exhibited more potent insecticidal activities than the precursor (+)-nootkatone after the introduction of 1,3,4-oxadiazole/thiadiazole on (+)-nootkatone. Among all of the (+)-nootkatone derivatives, compound 8c (1 mg/mL) exhibited the best growth inhibitory (GI) activity against M. separata with a final corrected mortality rate (CMR) of 71.4%, which was 1.54- and 1.43-fold that of (+)-nootkatone and toosendanin, respectively; 8c also displayed the most potent aphicidal activity against M. persicae with an LD50 value of 0.030 μg/larvae, which was closer to that of the commercial insecticidal etoxazole (0.026 μg/larvae); and 8s showed the best larvicidal activity against P. xylostella with an LC50 value of 0.27 mg/mL, which was 3.37-fold that of toosendanin and slightly higher than that of etoxazole (0.28 mg/mL). Furthermore, the control efficacy of 8s against P. xylostella in the pot experiments under greenhouse conditions was better than that of etoxazole. Structure-activity relationships (SARs) revealed that in most cases, the introduction of 1,3,4-oxadiazole/thiadiazole containing halophenyl groups at the C-13 position of (+)-nootkatone could obtain more active derivatives against M. separata, M. persicae, and P. xylostella than those containing other groups. In addition, toxicity assays indicated that these (+)-nootkatone derivatives had good selectivity to insects over nontarget organisms (normal mammalian NRK-52E cells and C. idella and N. denticulata fries) with relatively low toxicity. Therefore, the above results indicate that these (+)-nootkatone derivatives could be further explored as new lead compounds for the development of potential eco-friendly pesticides.
