CS270143B1 - Coordination compounds and method of their preparation - Google Patents

Abstract

The invention and the invention relates to kerinating compounds. n-ealicylKen - ^ - alaniaate-thiene • Cyanate «Beepataneous in the organic matter M [Cu (TSB) (SCN) J. χ H20, alk · m2 [cú (tsb) (scn) ^ 1. x h2o, where M denotes kain alkallke's kevu alek · ΝΗΪ, TSB marked iianiin tr * J4 «n * r · - in j l Schlff «ea iy ν ν ν ν ν ν ν ν ν ν ν ν ν β β β β β β β β β ní ní ní ní ní ní ní ní ní ní ní ní ní ní ní ní ní ní ní ní ní ní ní ní ní ní ní ní ní and saliijylaldehyium and x = 0, 1, 2 alek · 3} and s »k leh pripravy reakeiab! N-eallcyliién- / 3-alaninate 'Beinatýeh to "aplex" in [Cu 2 (TSB) 2 LJ. HgO ale- »I £ Cu (TSB) LO. x H20, kie L denotes k * «rdinevan je4n »4« nir * ex B «le llig y llig, usually H 2 O and x - 0, 1, 2 or 3, s ti * cyanate * B vBeCeReCeReRsMSCN, ▼ kt «r« B M denotes katlen alkallekéhk k vu alek »zNH .. Compounds Are Antibiotic najaS fungičine vlaetneeti.

Description

The present invention relates to coordinating compounds of the N-ealicylidene- (3-alaninato-thiocyanate) quinate type in the general formula

Mfcu (TSB) (SCN) D. x H ₂ 0, alaba

M ₂ CCu (TSB) (SCN) p. x _H2O wherein M is an alkali Katlan kevu or NH ^, TSB represents a tridentate dianion Schiffevej base 'dvodemej Edyy -alanine and ealicylaldehydu (O.CgH .CHoN.CHg.CHg.COO ^) ^2' and x '0, 1 , 2, or 3, as well as the preparation of these compounds.

The compounds of the invention are similar to the N-salicylidene-4-aminoalkaneate-thiocyanate-copper-coordinate compounds (J. Krtttsmár-ŠmogroviS, V. Sereesová, T. QaSová, Š. Várkonda and V, KeneSnýi. however, by coordinating TSB, they diverted from X-amlnokyoelin.

Coordination compounds of the molecular composition, of the N-saltidylidene-β-alaninate type complex of the general formula (CuB) II, are also known. x HgO, alek · CCu ₂ (TSB) ₂ lJ. HgO, where TSB ax represents it, is as in all compounds of the present invention and represents a coordinated HgO molecule, but is a single-function molecular ligand of the pyridine, urea, or thiomosomal type.

Said known types of coordinate compounds are important in several cases as simple models of biological systems, e.g. metalloenzines and also show anti-crab properties. Of these, N-alkanoyl-.alpha.-alaninate-ammonium coaplaxes, compounds of aloolytic composition, are almost insoluble in science, and their kegegal testing and applications are widely used. The N-salicylldene-4-aminoalkanoate-thiocyanatoanoates which are soluble in turn in turn generally show less biological activity than comparable compounds of the invention. .

In the chemical literature, dase terrified compounds of N-salicylidene-β-alaninate-type dianions, which bind to the SCN and another anionic Uganda do not form a camplex / anlone, a component in the M-Cu (SCN) (SCN) (SCN) , χ H ₂ 0, aleke m ₂ [cu (tsb) (scň) ₂ ·]. χ h ₂ o.

The description of the preparation of coordinating compounds is useful in the reactions of the corresponding starting materials of the type QCu ₂ (TSB) ₂ ^ or or (Cu (TSB)] 0 (the above abbreviations are the same as in the previous text), used in phenolic crystallite wastes, with an excess of MSCN in After cooling from the reactive systems, the compounds of the present invention crystallize in good yields as crystalline, green-colored products of a very good degree of crosslinking.

The selected examples illustrate but limit the general method of preparation of the compounds of the invention and characterize their combination as well as some properties and effects. Extract of the solids of the element (C, Η, N) and the solid-state epectral characteristics (non-gaseous suspension technique!) spectra, and also shows the antimicrobial activity of Escherichia coll, Staphylococcus aureus, Candida albicans, Microsporun gypseun and Trichophyton torrostro, characterized by minimal inhibition. concentration (MIC v / Ug.cm ~ ^) determined by the dilution method. The hairy values correspond to the organism in the given order.

Example 1 ‘'

5.45 g (Ό, ΟΪ mol) of aqua (N-salicylidene- (J-alaninato) disodium complex monohydrate are dissolved in 240 cm @ 3 of 75% ethanol at 60 DEG C., the mixture is filtered and dissolved. , 1 g (0.08 mol) of ammonium tocyanate in 40 cm 3 of water so that the temperature of the reactant system is 45 ° C. The mixture is then cooled to 0 DEG C. and the precipitated selenium-colored crystalline product ea, after isolation, is taken up in chilled ethanol and dried at room temperature. The yield of ammonium N-ealicylidene-β-alaninate-tocyanate monate is 75%. Analysis. Great HjjNjOjSCu C ^, M _r 330.8 J vypačítané / zietenéi · 35.93 / 39.85 0} £ 2.96 / 2.80 H; 7.47 / 7.60 Ν. Electro-opening ectron (VIS) with 1® 460 ca ^-1 . MIC j 600, 200, 700, 90, 200.

CS 270 143 Bl

Example 2

The working step is the same as in Example 1, except that 7.8 g (0.08 ml) of potassium tecyanate are used in place of the reaction. The yield of potassium N-alicylidene-4-alanine tecyanate is 79%.

Analysis. For C 1 H 9 N 2 O 2 SCuK, M _r = 351.9; calculated / found: 37.54 / 37.61% C; 2.58 / 2.73% H and 7.96 / 8.14% N. Electroelectric spectrum (VIS): λ = 14 7CO cm ^-1 . MIČ: 7CO, 200, 700, 90, 200.

Example 3

In a mixture of 64 cn? 5.45 g (0.01 ml) of aquacis (N-salicyliene-.alpha.-alaninate) menhydrate were dissolved in ethanol and 8 cm @ 3 of water and 6.48 g (0.08 ml) of sodium tecyanate were added. The reaction mixture is heated with stirring in a defective bath at a temperature of 70 DEG C. until the solid phase has dissolved. The system is filtered with a pellet and allowed to cool greatly on a laMeratern heat. The filtrate excluded kryčtály dark green Farkas pe edsatí the frit washed with ¹ echladeným etanelem usufiia and veins of lakeratérnej teplete. The yield of N-ealicylidene-4-alaninate bisacyanate) copper citrate dihydrate is 78%.

k Analysis. For M _y = $ 452.9 calculated / found: 31.82 / 31.88 C; 2.89 / 2.82% H; 9.28 / 9.20% N. Electrode spectrum (VIS): V _Bax = 15 460 cm ^-1 . MIC => 1000, 200, 800,) 1000, 200.

method of invention '

Claims (2)

1. Copper copper compounds of the general formula M [Cu (TSB) SCN)]. x H ₂ 0, aleke M ₂ £ Cu (TSB) (SCN) 2. H ₂ O wherein M is an alkaline Katie's kevu Aleke NH ^, TSB eznačuje dianién třejdenerevej Schiffevej base · (^ O.CgH .CH ₂ .CH = N.CH ₂ .COO) ² edvedenej ed ^ -alanine, and salicylaldehyde and x = 0 , 1, 2 aleke 3. 2. A description of the preparation of compounds of general formulas as in method 1 according to method 1, characterized in that the fermentation compound is reacted with a general formula (cu ₂ (TSB) ₂ or H ₂ 0 or (TSB) 1). ). x H ₂ 0 where L denotes the keerdined single-energy melecle ligand, usually HgO, TSB ax denotes the same as in the case l, with the cyanogen acetate of the general formula MSCN, in which M denotes the same as in the case 1, in the ratio 1: 2 to 1 : 8, in mixtures of ethanol: science in a ratio of 1.5: 1 to 8: 1 at temperatures of 45 to 70 ° C.