54,56-indium(iii)chlorine: 58,60-cobalt(ii)oxo-6,11:19,24:32, 37:45,50-tetramino - 5,52:of 13.18:20,31:39,44 - tetranitronaphthalene [c, g, e, p, u, y, d, h] (1,10,19,28 - tetraazacyclotetradecane with bacteriostatic action on staphylococcus and e. coli

 

(57) Abstract:

The proposed new bimetallic metalloorganicheskoi connection: 54,56-indium(III)chlorine: 58,60-cobalt(II)oxo-6,11: 19,24: 32, 37: 45,50-tetramino-5,52:of 13.18:20,31:39,44-tetranitronaphthalene [c,g, e,p,u,y, D,H](1,10,19,28)-tetraazacyclotetradecane formula I

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with bacteriostatic action on Staphylococcus and E. coli. Described by its synthesis. The proof structure is confirmed by elemental analysis, electronic and IR spectroscopy. 3 Il.

The invention relates to the field of synthesis of chemical compounds, specifically to the synthesis of metal complexes of macroheterocyclic compounds.

Known binuclear metal complexes 6,11:19,24:32,37:45, 50-tetramino-5,52: of 13.18: 20,31: 39,44-tetranitronaphthalene (c, g, e, p, u, y, D, H) (1,10,19,28)-tetraazacyclotetradecane with Co (II), Cu (II), Ni (II) with poluprovodnikovymi properties and is able to vothonas in vacuum [Smirnov, R. P., Andrianov centuries, Y. Vorobyev,, Shorin Century A. Fedorov, M. I. Synthesis and electrical properties of binuclear cobalt containing macroheterocyclic compounds. WPI. universities, Chemistry and chem. technology, 1984, T. 27, No. 10, S. 1239 - 1241].

The use of compounds of similar structure in the x solvents.

The task of the invention is the synthesis of bimetallic metal complex of macroheterocyclic compounds soluble in alcohols and with bacteriostatic effect on E. coli and Staphylococcus.

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Structure InClCoO2(MGCS) is confirmed by the method of synthesis, as well as elemental analysis data, vibrational and electronic spectroscopy.

InClCoO2(MGCS) synthesized template method based on diamino-sondigo [N. Neustroev. R. , Vorobyov, Y., Smirnov , R. P. Diamino-sondigo and its derivatives. Ivanovsk. state chem.-the technologist. academic., Ivanovo, 1994, Dept. in VINITI, Moscow 04.07.94, 1650-At-94]. The proposed connection relates to metal complexes azamacrocyclic compounds symmetric structure with covalent bond type metal - ligand. Structural differences from the closest analog metal complex 54,56: 58,60-dicobalt(II)dioxo-6,11: 19,24: 32,37: 45,50-tetramino - 5,52:of 13.18: 20,31: 39,44-tetranitronaphthalene[c, g, e,p,u,y,D,H] (1,10,19,28)-tetraazacyclotetradecane is that part of macroheterocyclic ligand molecules InClCoO2(MGCS) are different in the nature of metals: In (III) and Co (III) with the appropriate extravagantly.


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Example 1. InClCoO2(MGCS). 1 g of diamino-sondigo (0,004 g-mol), 0.3 g of cobalt acetate (0,0009 g-mol) and 0.5 g of chloride India (0.001 g-mol) in 100 ml of dry ethylene glycol is stirred for 15 minutes in an argon atmosphere. Then the reaction mixture is heated to the boil and continue stirring at this temperature for 20 hours, maintaining an atmosphere of inert gas. The formed precipitate is filtered off, washed with a small amount of a 5% HCl solution, then with 5% aqueous ammonia solution and water to neutral reaction, the acetone to conventional Soxhlet extractions. Dried at 100oC. the resulting product is subjected to chromatographic purification on a column filled with alumina. As eluent a mixture of chloroform-pyridine (8 : 1). Yield: 50%. Decomposes at 445oC, Rf = 0.75 in (Silufol, a mixture of pyridine-chloroform-1:5).

InClCoO2(MHCS) is a crystalline substance of a dark green colour. Soluble in pyridine, dimethylformamide, worse in alcohols. When dissolved in concentrated acid is destroyed.

Elemental analysis data satisfy the gross formula InClCoO2(MGCS):

C64H32N12InClCoO2.

Found, %: C 63,0; H 2,8; N 13,6; : were recorded on a spectrophotometer Specord M-40 - for the solution in dimethylformamide brand "chemically pure" in the region of 400 - 800 nm at a temperature of 298 K (Fig. 1).

In the electron spectrum InClCoO2(MGCS) observed four absorption bands in the visible region. Absorption bands in the region 406, 450 nm characterize -*electronic transitions in the system pair of separate fragments diamino-sondigo forming part of macroheterocyclic ligands, and the stripes in the field 605, 563 nm answer*electronic transitions due to the presence of a single closed-system coupling the tubes of the ligand.

Registration infrared spectra InClCoO2(MGCS) was performed on a spectrophotometer Specord - 75 IR in the region 4000 - 400 cm-1since the sample is pressed into a tablet with optically active potassium bromide (Fig. 2).

Mixing all of vibrations in molecules binuclear MGCS inherent, as is well known, vysokoodarennym structures [Kazicina L. A., Kupletskaya N. B. Application of UV, IR and NMR spectroscopy in organic chemistry. - M.: Higher school, 1971, 264 S.], leads to the fact that their spectra are virtually no bands characteristic oscillations. Relatively independent are the valence and non-planar deformation relations of the C-H isoindoline FR, is also deformation relations C-H (1050 - 1200 cm-1and the stretching vibrations of the C=C bond of the benzene ring in the region of 1600, 1580, 1500 cm-1. The absence of bands in the region 3300 - 3400 cm-1characterizing relatively independent of fluctuations in the relations N-H primary terminal amine groups and vnutrirossijskikh of aminogroup confirms the closed nature of the ligand in the molecule InClCoO2(MGCS) and their complete replacement of the ions of the respective metals: In (III), Co (III). Links M-N is confirmed by the band in the region of 400 - 500 cm-1[Kazicina L. A., Kupletskaya N. B. Application of UV, IR and NMR spectroscopy in organic chemistry. - M.: Higher school, 1971, 264 S.].

Determination of biological activity InClCoO2(MGCS).

Tests to determine the biologically active properties InClCoO2(MGCS) was performed according to the method of comparative evaluation delay of the colony of the test cultures, and defining the zones of lysis of these crops under the influence of the test substance.

As the test cultures used strains of Escherichia coli M-17 and Staphylococcus aureus (lec+). The original was preparing a saturated solution of the substance in ethanol, which was then brought to a volume of 10 ml in 100 ml of molten mycopathologia aaml. Wash daily culture of the studied strains of microorganisms was prepared according to the turbidity standard [Chitashvili R. P. , Osize D. F., Bianco Century A. Methodological guidance for the preparation and control of bacteriological culture media, Tbilisi, 1977, 158 S. ] , using for cultivation saline and then retireval to a final dilution of 10 - 6, i.e., the concentration of microorganisms in 1 ml of this dilution was dozens of cells of microorganisms. This cultivation was performed by inoculation of 0.1 ml of a suspension of the test cultures on Petri dishes containing the analyzed connection and control cups entered without substance. Crops thermostatically at a temperature 370,2oC. Evaluation of antimicrobial activity was carried out according to the results of colony after 24 hours.

The production of the second series of experiments consisted of the following: MPA (mastopathy agar) lawn was seeded test test-culture of microorganisms. After sowing, the Cup was passed to eliminate excessive moisture in the agar within 30 minutes, which is then in compliance with the rules of asepsis superimposed disks of filter paper soaked in the test solution. The disks are pre-sterilized in a dry-heat Cabinet, the PCC is Yah. Therefore eliminated the negative effect of solvent on the subjects of the test culture, which could skew the results and lead to incorrect interpretation.

In the course of the experiment, found no significant difference between control and experiment for the subjects of the test cultures, characterized by changing the diameter of the grown colonies (Fig. 3).

When measuring the diameter of colonies of E. coli in the experiment with the addition of tested compounds were found to decrease the diameter of the colonies at 30% (experiment with the addition of the test substance is D = 0.02 mm 1,98, control D = 2,83 0.03 mm). In a similar experiment using Staphylococcus aureus reduction of the diameter of the colonies was 27.5% (experiment D = 1,24 0,001 mm, control - D = 1,71 0.09 mm).

In the experiment the following data were obtained: for E. coli zone of stunting - 1,5 0,02 mm for Sth. aureus - 1,0 0,01 mm

Thus, the biological effects of the analyte of interest is expressed in the presence of a bacteriostatic effect on the test of culture, and in a few more respect for Escherichia coli M-17 than for Staphylococcus aureus.

Of particular interest in the experiment with Staphylococcus aureus caused the fact of formation of secondary growth front ku what about the impact of the analyte by Staphylococcus aureus cells with subsequent activation of their development.

The obtained data allow to draw conclusions about the biological activity of the proposed connection on the intraspecific effect of information transfer between cells, forced adaptation period to change the normal development of the colony.

To determine the toxicity InClCoO2(MGCS) by the method of [Besplatno, T. , moles Y. A. Maximum permissible concentrations of chemical substances in the environment. The Handbook. -L.: Chemistry, 1985, 350 S.] is defined temporarily permissible concentration of this compound in the air of working zone (VDK R. Z. ), which amounted to: VDK R. Z. = 0,87 mg/m3.

54,56-indium(III)chlorine: 58,60-cobalt (II) oxo-6,11:19,24:32,37:45,50-tetramino-5,52: of 13.18:20,31:39,44-tetranitronaphthalene [c, g, e, p, u, y, D, H] (1,10,19,28)-tetraazacyclotetradecane formula

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with bacteriostatic action on Staphylococcus and E. coli.

 

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