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Gholivand K Mojahed F Salehi M Naderi-Manesh H Khajeh K 《Journal of enzyme inhibition and medicinal chemistry》2006,21(5):521-525
Two novel structurally related phosphoramidate compounds, 1 and 2, with likely beta-diketone system were synthesized and characterized by 1H, 13C, 31P NMR, IR spectroscopy and elemental analysis. Compound 2 exhibited a 31P NMR signal which was significantly shielded (8 ppm) relative to compound 1. Determination of human erythrocyte acetylcholinesterase (hAChE) inhibitory activity was carried out according to Ellman's modified kinetic method and the IC50 values of compounds 1 and 2 were 1.567 and 2.986 mM, respectively. The k(i) values of 1 and 2 were 1.39 to 2.65 min(-1) respectively. A comparison of the bimolecular rate constant (k(i)) and IC50 values for the irreversible inhibitors 1 and 2 revealed that the oxono analogue has greater affinity for hAChE than the thiono compound. Furthermore effects of two conventional oximes paralidoxime (A) and obidoxime (B) on reactivation of the inhibited hAChE were studied but low reactivity was shown by both the oximes. 相似文献
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Gholivand K Alizadegan AM Firooz AA Khajeh K Naderi-Manesh H Bijanzadeh H 《Journal of enzyme inhibition and medicinal chemistry》2006,21(1):105-111
Carbacylamidophosphates with the general formula RC(O)NHP(O)R1R2 constitute organophosphorus compounds that are used as insecticides, pesticides and ureas inhibitors. In this work, we studied the inhibition potency of CCl3-C(O)NHP(O)Cl21, CHCl2C(O)NHP(O)Cl(2)2, CH2ClC(O)NHP(O)Cl23 and CF3C(O)NHP(O)Cl(2)4, which are the major intermediates for carbacylamidophosphates synthesis towards human erythrocyte acetylcholinesterase (hAChe) activity using Ellman's modified kinetic method. Unexpectedly, it was observed that they were not only hydrolytically unstable but also inhibited hAChE in a similar manner to that produced by organophosphorus insecticides. Enzymatic data, bimolecular inhibition rate constants (ki) and IC50 values for inhibition of hAChE demonstrated that they are irreversible inhibitors and the inhibition potency of compound 2 (IC50 = 88 microM) was the greatest in comparison with compounds 1, 3 and 4. Also the electropositivity of the phosphorus atom and the hydrophobicity of the compounds demonstrated that these two factors play an additional effect and different role in the inhibitory activity of these compounds. Hydrolytic stability of the compounds was determined by 31P NMR monitoring of the loss of the parent molecules with D2O as a function of time. This study considers antiacetylcholinesterase activity according to the structural and the electronic aspects of compounds 1-4, according to IR, 1H, 13C and 31P NMR spectral data. 相似文献
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Ayyub Mojaddami Sedigheh Abedanzadeh Mehrafarin Bagherzadeh Gisou Foroutan Mohammad Javad Khodayar Mohammad Panahimehr Masood Fereidoonnezhad 《化学与生物多样性》2023,20(7):e202201177
Platinum-based drugs have been widely used in cancer treatment. However, their severe side effects have limited their use. So, researchers have been striving to find compounds with fewer side effects and greater efficacy, to overcome these drawbacks. Here, the cytotoxicity of platinum(II) complexes containing 2-(diphenylphosphino)pyridine ligands have been studied on human lung (A549), ovarian (SKOV3), breast (MCF-7) cancer, and normal breast (MCF-10A) cell lines. The most potent compound exhibits a marked cell growth-inhibitory effect against ovarian and lung cancer cells with IC50 values of 9.41 and 5.58 μM, respectively, which were significantly better than that observed for cisplatin (19.02, and 8.64 μM). Additionally, all complexes achieved significantly lower cytotoxicity towards MCF-10A. To investigate the interaction of complexes with DNA, an electrophoresis mobility shift assay was conducted, which indicated that complexes bind to DNA and affect its electrophoretic mobility. An analysis of apoptosis in A549 cells supported the conclusion that they inhibits cell proliferation via induction of apoptosis in a concentration-dependent manner. Molecular docking was also used to investigate the interactions of compounds with different DNA structures. These compounds have the ability to be a suitable pharmaceutical compound with further investigations in the field of cancer research. 相似文献
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Gholivand K Abdollahi M Mojahed F Alizadehgan AM Dehghan G 《Journal of enzyme inhibition and medicinal chemistry》2009,24(2):566-576
Eight newly synthesized carbacylamidophosphates with the general formula RC(O)NHP(O)Cl2 with R = pCl-C6H4 1a, pBr-C6H4 2a, C6H5 3a, and pMe-C6H4 4a and RC(O)NHP(O)(NC4H8O)2 R = pCl-C6H4 1b, pBr-C6H4 2b, C6H5 3b, pMe-C6H4 4b, were selected to compare the inhibition kinetic parameters, IC50, Ki, kp and KD, on human erythrocyte acetylcholinesterase (hAChE) and bovine serum butyrylcholinesterase (BuChE), Also, the in vivo inhibition potency of compound 2a, 2b and 3a, were studied. The data demonstrates that compound 2a and compound 2b are the potent sensitive as AChE and BuChE inhibitors respectively, and the inhibition of hAChE is about 10-fold greater than that of BuChE. 相似文献
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Khodayar?GholivandEmail author Mohammad?Kahnouji Yazdan?Maghsoud Ehsan?Masumian Mahdieh?Hosseini 《Journal of molecular modeling》2018,24(11):328
The selectivity of phosphoryl P(O)R3, sulfoxide S(O)R2, and carbonyl C(O)R2 (R?=?NH2, CH3, OH, and F) derivatives with lanthanide cations (La3+, Eu3+, Lu3+) was studied by density functional theory calculations. Theoretical approaches were also used to investigate energy and the nature of metal–ligand interaction in the model complexes. Atoms in molecules and natural bond orbital (NBO) analyses were accomplished to understand the electronic structure of ligands, L, and the related complexes, L–Ln3+. NBO analysis demonstrated that the negative charge on phosphoryl, carbonyl, and sulfoxide oxygen (OP, OC, and OS) has maximum and minimum values when the connected –R groups are –NH2 and –F. The metal–ligand distance declines as, –F?>?–OH?>?–CH3?>?–NH2. Charge density at the bond critical point and on the lanthanide cation in the L–Ln3+ complexes varies in the order –F?<?–OH?<?–CH3?<?–NH2, due to greater ligand to metal charge transfer, which is well explained by energy decomposition analysis. It was also illustrated that E(2) values of Lp(N)?→?σ*(Y–N) vary in the order P=O ? S=O ? C=O and the related values of Lp(N)?→?σ*(Y=O) change as C=O ? S=O ? P=O in (NH2)nYO ligands (Y?=?P, C, and S). Trends in the L–Ln3+ CP–corrected bond energies are in good accordance with the optimized OY?Ln distances. It seems that, comparing the three types of ligands studied, NH2–substituted are the better coordination ligands. 相似文献
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Khodayar Gholivand Hamid Reza Mahzouni Mehrdad Pourayoubi Shadi Amiri 《Inorganica chimica acta》2010,363(10):2318-4308
Monodentate and bidentate ligands PhNHP(O)(NC4H8O)2 (1) and PhC(O)NHP(O)(NH(tert-C4H9))2 (2) were used to prepare new 7, 9 and 10-coordinated lanthanum(III) complexes; La(1)2Cl3(H2O)2 (3), La(1)2(NO3)3H2O.La(1)2(NO3)3CH3CN (4) and La(2)2(NO3)3 (5), respectively. Crystallization of compound 2 in CH3OH:CH3CN leads to one conformer in contrast to the crystallization result from CHCl3:n-C7H16 (two conformers). Compound 4 contains two independent nine-coordinated La(III) complexes that are different in the solvated molecules (H2O and CH3CN). Some structural and electronic perturbations in coordinated ligand were occurred upon complexation, that are confirmed by increase of 2JPH, 3JPH and 6JPH coupling constants from the free ligand 1 to complexes 3 and 4. The steric repulsions in the first coordination sphere of La3+ ion, metal-ligand (M-L) binding strength and PO stretching frequency are very influenced by changing the counter ion from Cl− to . Comparing the X-ray crystallography data of free ligand 2 with bis-chelated complex 5, it is found that the phosphoryl group is more reactive than carbonyl counterpart. A blue shift of the ν(N-H) vibration is observed in line with the weakening of the hydrogen bond from N-H···OPhosphoryl in 1 to N-H···Cl in 3. Three dimensional butterfly-shape structures are seen in the unit cell of complex 3, which are produced by OWater-H···OMorpholine hydrogen bonds. 相似文献
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Gholivand K Shariatinia Z Khajeh K Naderimanesh H 《Journal of enzyme inhibition and medicinal chemistry》2006,21(1):31-35
The ability of phosphoramidates Me2NP(O)(Cl)(p-NHC6H4NO2) 1, Me2NP(O)(p-NHC6H4NO2)2 2, (CH3C6H4O-p)P(O)(p-NHC6H4NO2)2 3 and (CH3C6H40-p)2P(O)(p-NHC6H4NO2) 4 to inhibit human acetylcholinesterase (hAChE) has been evaluated by a modified Ellman's method and spectrophotometric measurements. Results showed that compounds 1 and 2 do not have any inhibitory potency, whereas compounds 3 and 4 were reversible mixed inhibitors. The IC50 values for inhibitors 3 and 4 were 0.143 and 0.581 mM, respectively. The previously unknown compounds 3 and 4 were synthesized and characterized by 1H, 13C, 31P NMR and IR spectroscopy and elemental analysis. 相似文献