Trans-sodium dichloro(bromo)-bis*01(gamma-1,2,5-trimethyl-4-(3,4 - dimethyl-3,4-dihydroxy-1-pentenyl)-4-piperidin this,n*01) platinum (ii), showing antihelminthic activity

 

(57) Abstract:

Usage: in medicine as an anthelmintic agent. The inventive product transmisora(bromo)-bis{gamma - 1,2,5-trimethyl-4-(3,4-dimethyl-3,4 - dihydroxy-1-pentenyl)- 4-piperidin this, N} Pt (II) of the formula [Pt(C15H27NC3)2Cl2]. Output 0,78 g (80%). Reagent: aqueous solution of K2[PtCl4] K2[PtBr4] . Reagent 2: gamma-1,2,5-trimethyl-4-(3,4 - dimethyl-3,4-dihydroxy-1 - pentenyl)-4-piperidin in alcohol. Reaction conditions: the process is conducted by heating to 40oC, 24 h table 1.

The invention relates to new chemical compounds, specifically to derived TRANS-sodium dichloro(bromo)-bis{ gamma-1,2,5-trimethyl-4-(3,4-dimethyl-3,4 - dihydroxy-1-pentenyl)-4-piperidin this, N}Pt (II), General formula

< / BR>
where

X is Cl or Br;

- the remainder of the ligand-gamma 1,2,5-trimethyl-4-(3,4-dimethyl-3,4-dihydroxy-1-pentenyl)-4-piperidone,

showing anthelmintic activity.

The aim of the invention is the synthesis of the compounds of bis-acetylene complexes of platinum (II) with a high coordination number, which could be used as medicines, in particular deworming profile.

Bis or potassium tetrabromophthalate (II)- 1,2,5-trimethyl-4(3,4-dimethyl-3,4-dihydroxy-1-pentenyl)-4-piperidone in aqueous - alcoholic medium at room temperature with a ratio of the original 1: 2. Synthesis at this ratio, the original complex bidentetea acetylene ligand (ligand containing two reaction centre) has resulted in a rich compound of bivalent platinum with coordination number equal to six (K. h=6).

The synthesis is useful to a small excess platinate (0.01 g) in water-ethanol solution (1:0,7). Stirring for 30 min in a water bath (t=40oC) the colour of the solution changed from red to dark brown, at room temperature the reaction mixture was left for 24 hours and Then added a 10-fold excess of acetone to remove from the reaction mixture by-product of KCl and excess of the original K2(PtCl4). Acetone drove on a rotary evaporator, the residue was treated with dry benzene and ether, dried in a vacuum desiccator over potassium. The yield of the target product 80%.

These bis-acetylene complexes of platinum (II) are pharmacologically active compounds and can be used as a deworming drugs.

Example 1. TRANS-sodium dichloro-bis{gamma-1,2,5-trimethyl-4-(3,4-dimethyl-3,4-dihydroxy-1 - pentenyl)-4-piperidin this, N}] platinum (II).

To 0.52 g (1.2 mmol + 0.01 excess) K2[PtCl4oin a water bath, the red solution turned into dark brown. The synthesis proceeded 24 hours Then was added 100 ml of acetone, vydeleny from the reaction mixture KCl was filtered, washed with acetone and removed. The acetone from the dark brown filtrate was off on a rotary evaporator. The residue was treated with dry benzene and ether, dried in a vacuum desiccator over potassium. Synthesized TRANS-sodium dichloro-bis { gamma-1,2,5-trimethyl-4-(3,4-dimethyl-3,4-dihydroxy-1-pentenyl)-4 - piperidin this, N} platinum (II) brown, soluble in DMF, ethanol, worse in acetone and water. Output [Pt(C15H27NO3)2Cl2] is 80% (0,78 g).

Found, %: C 45,00, H 7.03 Is, 3,57, Cl 9,07, Pl 24,72.

Calculated, %: C 44,77, H Is 6.78, 3,48, Cl 8,81, Pl 24,24.

Example 2. TRANS-dibromo-bis {gamma-1,2,5-trimethyl-4(3,4-dimethyl-3,4-dihydroxy-1-pentenyl)-4-piperidin this, N} platinum (II).

To 0.51 g (1.0 mmol + 0.01 g excess) K2[PtBr4] in 10 ml of H2O added 1,357 g (2 mmol) of gamma-1,2,5-trimethyl-4-(3,4-dimethyl-3,4-dihydroxy-1-pentenyl)-4-piperidone in 7 ml of ethanol. After 15 min when heated to 40oC in a water bath, the red solution turned brown. After 24 h were processed similarly to enter the - 4-piperidin this, N} platinum (II) light brown, soluble in DMF, ethanol, worse in acetone in water. Output (Pt(C15H27NO3)2Br2] is 80% (of 0.62 g).

Calculated, %: C 40,31, H 6,05, N 3,14, B 17,92, Pt 21,84.

Found, %: C 40,54, H 6,35, N 3,45, B MT 18: 34, Pt 22,07.

The above synthesis proceeds according to the following scheme

< / BR>
Absorption band (Pt (C15H27NO3)2Cl2] in the infrared spectrum: 330, 2980, 2935, 2885, 2730, 2695, 2650, 2560, 2545, 2515, 2080, 1465, 1385, 1365, 1345, 1330, 1280, 1245, 1185, 1145, 1080, 995, 965, 910, 890, 885, ..., 320 (cm-1). IR-spectrum (Pt (C15H27NO3)2Br2] is identical to the above, only in the long wavelength region observed absorption band Pt - Br at 234 cm-1.

Ligand coordinated bidentate: triple bond and the nitrogen piperidine cycle: CC= 155 cm-1in the region of lower frequenciesCC= free ligand 2225 cm-1) CH9N = 200 cm-1in the region of lower frequencies (CC= free ligand 2850, 2827, 2815 cm-1). The signal is coordinated nitrogen atom in the NMR spectrum14N -311 memorial plaques In the NMR spectrum13C signals carbon triple bond and a carbon linked to the nitrogen atom, are in a weaker field relative to their position in splenocyte ligands, coordinated by a triple bond and a nitrogen atom.

Laboratory studies on TRANS-sodium dichloro-bis/gamma-1,2,5-trimethyl-4-(3,4-dimethyl-3,4-dihydroxy-1-pentenyl)-4-piperidin this, N) platinum (II) showed that bis - complex showed anthelmintic activity. The tests were performed on all mice in laboratory animals Nippostrong jlus Brasiliensis, the causative agents of the disease (nippostrongylus.

The purpose of these tests was to identify properties depending on the concentration of added compounds. The control were infective larvae helminth Nippostrongylus Brasiliensis in physiological solution (0,850-hydrated NaCl) tests were carried out in comparison with chetyrehkratnym acetylene complex of Pt (II) dichloride/3-methyl-3-methoxy-1-butyn/platinum (II) (LD50= 2000 mg) (kg, USSR author's certificate 1496228, class C 07 F 15/00, 1989) from 5 mg to which the death of worms occurs within 1.5 hours

Example 3. In a cell with a volume of 1-2 ml pour 0.1 ml suspension of worms (in 0.1 ml suspension of helminths in physiological solution of 0.85% NaCl by centrifugation at 1000-1500 rpm for 5-10 min and aspiration of the supernatant layer to achieve the concentration of helminth 50-100 copies). Then make a TRANS-sodium dichloro-bis{ Gatow 1, 2, 3, 4, 5, 6, 7, 10 mg. Experiments were carried out at a temperature of 37oC, because the worms are maximum mobility when 37-45oC. Watched the death of the worms during visually at different magnifications of the microscope MBS-1. Adding 1 mg of the tested synthetic resins death of worms comes after 3.5 h, 2 mg, 2.5 h, 3 2 h 20 min, 4 - 1 h 40 min, 5 - 1 h 15 min, 7 - 1 h 15 min, 10 mg - 1 h 15 min, monitoring helminths is more difficult, because the background is overloaded with excess substance.

Conducted research shows that TRANS-sodium dichloro-bis-{ gamma-1,2,5-trimer-4-/3,4-dimethyl-3,4-dihydroxy-1-pentenyl/- 4-piperidin this, N} platinum (II) possesses anthelmintic activity that causes 100% mortality Nippos. brasilunsis, LD50=2000 mg, and has a greater nematocides in comparison with dichloride(3-methyl-3-methoxy-1-buten) platinum (II) because of the death of worms comes on 15 minutes faster (see table).

TRANS-sodium dichloro(bromo)-bis{ gamma-1,2,5-trimethyl-4-(3,4-dimethyl-3,4-dihydroxy-1-pentenyl)-4-piperidin this, N} platinum (II), General formula

< / BR>
where X = Cl or Br;

- the remainder of the ligand gamma-1,2,5-trimethyl-4-(3,4-dimethyl-3,4-dihydroxy-1-pentenyl)4-piperidone,

showing anthelmintic activity.

 

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