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Семина, И. И.; Shilovskaya, E. V.; Тихонова, Н. А.; Байчурина, А. З.; Tarasova, R. I.; Гараев, Р. С.

doi:10.1023/a:1016055211321

Cited by 7 publications

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“…The antidepressant properties, effects on memory and learning processes, and the neuroprotector and membranotropic action of compounds I and II were studied as described elsewhere [10,11,19,20].…”

Section: Methods Of Investigationmentioning

confidence: 99%

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Comparative study of the structure and biological activity of potential psychotropic drugs phosenazid and CAPAH

et al. 2007

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Data of IR, UV, and NMR ( 31 P, 1 H, 13 C) spectroscopy, X-ray crystallography, and quantum chemical calculations are presented for phosenazid and CAPAH molecules possessing psychotropic properties. In comparison to phosenazid, CAPAH exhibits a broader spectrum of neurotropic activity, which can be related to the presence of the P1 -O3 polar ester bond and, therefore, a higher reactivity of this molecule in metabolic processes. 690091-150X/07/4102-0069

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Section: Methods Of Investigationmentioning

confidence: 99%

“…In addition, clinical investigations showed that phosenazid exhibits nootropic and antidepressant properties [7,8]. In the stage of experimental investigation, CAPAH showed neuroprotector and antidepressant properties and improved memory function [9], which suggests that this compound can be classified as a nootrope with antidepressant component [10].…”

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Comparative study of the structure and biological activity of potential psychotropic drugs phosenazid and CAPAH

et al. 2007

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“…As with bromoacetates, 1 the reactions gave cyclic (3) and acyclic products (4). According to 31 P NMR data, their ratio is virtually independent of the nature of the substitu ent R 1 at the N atom in oxazaphosphinanes 1 but is deter mined by the substituent R 2 in the alkoxy group (Table 1).…”

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confidence: 94%

“…2 It is known that condensation products of phosphorylacetic acid and amino acids, e.g., with aspartic acid (PALA preparation), are strong carcino lytics 3 and the corresponding hydrazides exhibit anti amnestic, antihypoxic, and antidepressant activities. 4 In connection with this, it was of interest to synthesize a series of 1,3,2 oxazaphosphinane analogs of these and some structurally related compounds.…”

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1,3,2-Oxazaphosphinane analogs of phosphorylacetic acid derivatives: synthesis and properties

et al. 2005

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Reactions of 2 AlkO 1,3,2 oxazaphosphinanes with alkyl N haloacetylamino or N chloro methyl N methoxycarbonylamino carboxylates mainly give products with retention (Alk = Me) and opening of the ring (Alk = Et). In aqueous solution, cyclic products with the N isopropyl group are only stable, while the rest undergo hydrolysis with cleavage of the P-N bond of the ring. Oxazaphosphinane analogs of phosphorylacetamide and phosphorylacetohydrazide were synthesized.Key words: 2 alkoxy 1,3,2 oxazaphosphinanes, 2 alkoxy 3 alkyl 1,3,2 oxazaphosphinanes, the Arbuzov rearrangement, alkyl haloacetylamino carboxylates, N chloromethyl N methoxy carbonylglycine methyl ester, N [(2 oxo 1,3,2λ 5 oxazaphosphinan 2 yl)acetyl]glycine methyl ester, hydrolysis, alkyl N [(3 alkyl 2 oxo 1,3,2λ 5 oxazaphosphinan 2 yl)acetyl]amino carboxy lates, N {[(3 bromopropylamino)ethoxyphosphoryl]acetyl}glycine methyl ester, N [(3 isopro pyl 2 oxo 1,3,2λ 5 oxazaphosphinan 2 yl)methyl] N methoxycarbonylglycine methyl ester,Earlier, 1 we have described synthesis of 1,3,2 oxaza phosphinane analogs of phosphorylacetates with poten tial biological activity, in which, by analogy with carcino lytic cyclophosphamide, the oxazaphosphinane ring plays the role of a "carrier" of a pharmacophoric group to a cell through cell membranes. 2 It is known that condensation products of phosphorylacetic acid and amino acids, e.g., with aspartic acid (PALA preparation), are strong carcino lytics 3 and the corresponding hydrazides exhibit anti amnestic, antihypoxic, and antidepressant activities. 4 In connection with this, it was of interest to synthesize a series of 1,3,2 oxazaphosphinane analogs of these and some structurally related compounds.1,3,2 Oxazaphosphinane analogs of phosphorylacetic acid containing fragments of amino acid esters were syn thesized by the Arbuzov reaction described in detail for the reactions of 2 alkoxy 3 alkyl 1,3,2 oxazaphosphin anes (1) with bromoacetates. 1 In the present work, com pounds 1 reacted with alkyl N haloacetylamino carboxy lates (2) (Scheme 1).Reactions with N bromoacetyl derivatives were car ried out in benzene at 20-50 °C, while those with N chloroacetyl derivatives, in toluene at 100-110 °C. As with bromoacetates, 1 the reactions gave cyclic (3) and acyclic products (4). According to 31 P NMR data, their ratio is virtually independent of the nature of the substitu ent R 1 at the N atom in oxazaphosphinanes 1 but is deter mined by the substituent R 2 in the alkoxy group (Table 1). For instance, for R 2 = Me, cyclic products are dominant (the ratio 3 : 4 varies from 93 : 7 to 86 : 14), while for R 2 = Et, the major product is an acyclic one (3 : 4 = 25 : 75)*. For pairs of compounds 3f, 4g and 3g, 4h, the 31 P NMR spectra in benzene show doubled signals due to diastereomeric anisochronism.The use of oxazaphosphinane 1d in the Arbuzov reac tion with N chloromethyl N methoxycarbonylglycine methyl ester (5) (Scheme 2) afforded cyclic (6) and acy clic products (7) in the 82 : 18 ratio ( 31 P NMR).In this case, the 31 P NMR spectrum...

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“…We have used 3~p nuclear magnetic resonance (NMR) and Fourier transform inffared (FTIR) spectroscopies and correlated the obtained results with the pharmacological effect of other nootropics to get a more detailed molecular basis of the primary pharmaeological effect of these drugs. Phosenazid is permitted for wide use as tranquilizer [5], nootropic [6], antidepressant [7] and antialcoholic drug [8]. The advantage of the chosen experimental methods is that the two techniques could provide complementary information about the mobility of both polar head groups and fatty acid chains as well as about the behavior of the dipalmitoyl phosphatidylcholine-water system as a whole.…”

Section: Introductionmentioning

confidence: 99%

31P NMR and FTIR studies on the interaction of phosphorylacetohydrazides with dipalmitoyl phosphatidylcholine model membranes

et al. 2004

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The effect of original synthetic nootropic drugs (phosphorylacetohydrazides) on the physical properties of the dipalmitoyl phosphatidylcholine (DPPC) membranes was studied by 3lp nuclear magnetic resonance and Fourier transform infrared spectroscopies. Ir has been shown that the tested preparations reduce the phase transition temperature, widen the transition interval, suppress pretransition, render some condensing effect on the gel phase and essentially disorder the lipid bilayer in the liquid-crystalline state. The obtained results are in agreement with the suggested rnechanism of the primary pharmacological effect of nootropic preparations. According to this mechanism, the drug molecules penetrate into the hydrophilic region of the bilayer, interacting closely with the polar groups of DPPC, disturbing the bilayer organization and leading to polymorphism. By taking into account that the main property of nootropic preparations is to improve processes of training and memory, we suppose that the new lipid-drug organization of phospholipidic membranes and lipid polymorphism are the necessary steps of the nootropic activity. The similarity of molecular mechanisms of various nootropic drug effects on the lipid bilayer allows us to suppose that the positive effect of nootropics on the synaptic transmission may be governed by their influence on the phase transition of the lipid component of the synaptic membranes at the stage of the neurotransmitter release.

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Cited by 7 publications

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Comparative study of the structure and biological activity of potential psychotropic drugs phosenazid and CAPAH

Comparative study of the structure and biological activity of potential psychotropic drugs phosenazid and CAPAH

1,3,2-Oxazaphosphinane analogs of phosphorylacetic acid derivatives: synthesis and properties

31P NMR and FTIR studies on the interaction of phosphorylacetohydrazides with dipalmitoyl phosphatidylcholine model membranes

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