Synthesis, characterization, oxidative degradation, antibacterial activity and acetylcholinesterase/butyrylcholinesterase inhibitory effects of some new phosphorus(V) hydrazides

Gholivand, Khodayar; Hosseini, Zahra; Farshadian, Sedigheh; Naderi-Manesh, Hossein

doi:10.1016/j.ejmech.2010.08.025

Cited by 29 publications

(22 citation statements)

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“…Gholivand [15] provide interesting studies about new phosphorus(V) hydrazides. Synthesised compounds have not only some antibacterial activity but are able to slow down AChE and BuChE (mainly) activity measured by Ellman's method [16].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, biological activity and HPLC validation of 1,2,3,4-tetrahydroacridine derivatives as acetylcholinesterase inhibitors

Szymański

Karpiński²,

Mikiciuk-Olasik

2011

European Journal of Medicinal Chemistry

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Section: Introductionmentioning

confidence: 99%

Synthesis, biological activity and HPLC validation of 1,2,3,4-tetrahydroacridine derivatives as acetylcholinesterase inhibitors

Szymański

Karpiński²,

Mikiciuk-Olasik

2011

European Journal of Medicinal Chemistry

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“…To continue our previous research, and considering the key role of the carbonyl group in the stated configurational change in the phosphorus atom, we chose aliphatic methyl and tert-butyl carbazates with formula NH 2 -NH-CO-OR, R = CH 3 and C(CH 3 ) 3 , respectively, to react with various phosphoryl intermediates, (R 0 ) 2 POCl and R 0 POCl 2 (R 0 = PhO, Ph, PhNH, 4-CH 3 C 6 H 4 O). The 2 J PNH values in the P-NH-N unit are reasonably high [19][20][21][22] and show a strong relationship with the starting phosphoryl reagents. The crystal structure, hydrogen bonding motifs, and intermolecular interactions of compounds 1, 2, and 5 have been further studied.…”

Section: Introductionmentioning

confidence: 87%

“…[12][13][14][15] In addition, phosphorus hydrazides have been considered as biologically relevant materials, when interacting with metallic radioisotopes for potential cancer diagnosis and therapy. 19 Recently, we reported a novel method for the preparation of spiro-bicyclophosphoranes by the reaction of phosphoryl containing reagents with aromatic hydrazides (benzhydrazide and 4-pyridinecarboxylic acid hydrazide), 20 in which the primary phosphorylation is followed by a structural rearrangement to trigonal bipyramidal phosphorus. 19 Recently, we reported a novel method for the preparation of spiro-bicyclophosphoranes by the reaction of phosphoryl containing reagents with aromatic hydrazides (benzhydrazide and 4-pyridinecarboxylic acid hydrazide), 20 in which the primary phosphorylation is followed by a structural rearrangement to trigonal bipyramidal phosphorus.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and structural study of some new phosphorus(v) hydrazide compounds: spectroscopic evidence and a theoretical approach

Gholivand

Molaei

2015

New J. Chem.

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New phosphorus(V) hydrazide compounds containing the [-P(O)NHNHC(O)OR] fragment have beenprepared by the reaction of mono-and di-chloro phosphoryl intermediates with methyl (R = CH 3 , 1-5) and tert-butyl (R = C(CH 3 ) 3 , 6-9) carbazates, and characterized by IR and multinuclear NMR spectroscopy.Molecular structures of 1, 2, and 5 have been established by X-ray diffraction analysis to investigate the relative orientation of the present moieties, resulting hydrogen bonding motifs and stabilizing intermolecular interactions. The impact of the intermolecular contacts on crystal packing has been further studied by Hirshfeld surface analysis. The dependence of experimental d 31 P and 2 J PNH values on phosphorus substituents has been explored using natural bond orbital (NBO) analysis. Likewise, the reasons for maintaining the tetrahedral geometry around the phosphorus atom in the synthesized compounds and not rearranging to a trigonal bipyramidal one (in comparison with spirophosphoranes) have been investigated theoretically. Overall, the NBO results reveal the influential role of electronic delocalization and s-content in hybridization for the above-mentioned experimental evidence.

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“…The first is acetylcholinesterase (AChE, EC.3.1.1.7), which is systematically called acetylcholine acetylhydrolase. The second is butyrylcholinesterase (BChE, EC.3.1.1.8), referred to systemically as acylcholine acylhydrolase (Gholivand et al, 2010). The preferred substrate for AChE enzymes is acetylcholine; BChE enzymes prefer butyrylcholine and/or propionylcholine, depending on the species .…”

Section: A Kinetic Characterization Of Acetylcholinesterase and Butyrmentioning

confidence: 99%

Poster presentations

2011

Advances in Animal Biosciences

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The key to maximising the nutritional value of lignocellulosic materials is in disrupting the plant cell walls to allow complete access to nutrients and not creating extra anti-nutritional factors (Castro et al., 1994). In particular, steam and pressure treatments to disrupt lignocellulosics in a way which allows improved utilisation of cell wall polysaccharides by rumen microbes (Castro and Machado, 1990). Rumen fungi produce a wide range of polysaccharide degrading enzymes and are as primary colonisers of fibrous plant materials that degrade lignin-containing plant cell walls. With the advancement of molecular enumeration methods, in particular 18S rDNA gene probing methods, researchers were able to monitor fungal species within the rumen (Stahl et al., 1998). Quantitative competitive PCR (QC-PCR) techniques play an important role in nucleic acid quantification because of their significant lower cost of equipment and consumables (Franz et al., 2001).The aim of this study was to use QC-PCR to determine the effect of sugarcane pith treated with low temperature steam plus 0.9% H 2 SO 4 on in vitro growth of rumen anaerobic fungi. Material and methods Rumen fungi were isolated from pre-incubated wheat straw in the rumen of fistulated sheep and then method of Joblin (1981) was used to grown under anaerobic conditions at 39ºC for 3 days. These isolates were used (1:9) as a source of fungi inoculum. Serum bottles (four replicate per sample) containing fungi culture medium, 1g of sugarcane pith as untreated (UTP) or treated with low temperature steam (at 135 ºC for 80 min) and 0.9 % H 2 SO 4 (STP) and 1ml antibiotic solution were used to culture the isolated fungi at 39ºC in an incubator. To preparing fungi pure culture, sub-culturing was done three times. Total genomic DNA was isolated from pure culture samples using Guanidine Thiocyanate-Silica Gel method. A universal PCR primer pair GAF (F): 5'-GAG GAA GTA AAA GTC GTT AAC AAG GTT TG-3' and GAF(R): 5'-GAAATT CAC AAA GGG TAG GAT GAT TT-3' was used to amplify a specific region of 18S rDNA from anaerobic rumen fungi. Standard control DNA was constructed to use in the QC-PCR and was shown to amplify under the same reaction condition and the same amplification efficiency as the target DNA. The PCR was performed in a final volume of 25µl sealed in a capillary tip, and thermocycling was carried out in a model 2000 (Biometra). The PCR amplification condition was as follows: denaturation at 94°C for 4min followed by 35 cycles of 94 °C for 30s; 56°C for 30s; and 72°C for 1min followed by a final extension at 72°C for 5min. The PCR products were separated by electrophoresis on agarose gels, stained with ethidium bromide, and visualized by UV transillumination. The relative intensities of PCR products were used to compare fungal biomass under different samples. The signal intensity was quantified by Image J 1.29x and expressed in arbitrary units. The data was analysed using the GLM procedure of SAS for a completely randomized design.

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Synthesis, characterization, oxidative degradation, antibacterial activity and acetylcholinesterase/butyrylcholinesterase inhibitory effects of some new phosphorus(V) hydrazides

Cited by 29 publications

References 40 publications

Synthesis, biological activity and HPLC validation of 1,2,3,4-tetrahydroacridine derivatives as acetylcholinesterase inhibitors

Synthesis, biological activity and HPLC validation of 1,2,3,4-tetrahydroacridine derivatives as acetylcholinesterase inhibitors

Synthesis and structural study of some new phosphorus(v) hydrazide compounds: spectroscopic evidence and a theoretical approach

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