20(29)-lupen-[(2,3:3,4)-5,5-dimethylhexane-2-it]-28-oic acid having coagulation activity

 

(57) Abstract:

Synthesized new derived lupina :20(29)- lupen-(2,3:3,4)-5,5-dimethylhexane-2-he-28-OIC acid. The synthesis is carried out by reaction of cyclization by Robinson from betulone acid and oxide mesityl. The compound obtained shows coagulation activity in combination with low toxicity. table 1.

The invention relates to chemical-pharmaceutical industry, namely to new biologically active substances on the basis of which can be created drugs that have coagulation activity.

The claimed compounds are new derived lupena, namely 20(29)-lupen(2,3:3,4)-5,5-dimethylhexane-2-one)-28-OIC acids of the formula:

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Cited in the application derived lupena, its properties and biological activity not described in literature.

The closest analogue of the structure is belanova acid, does not possess biological activity /5/:

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Similar in action to the claimed connection is menadione /1/.

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The aim of the invention is to obtain a new derivative of lupine with more pronounced coagulation activity.

Put rebetolbuy acid and oxide mesityl.

Example. 20(29)-lupen-(2,3:3,4)-5,5-dimethylhexane-2-he-28-OIC acid: 0.5 M betulone acid dissolved in 250 ml ethanol containing 0.25 g sodium hydroxide, cold added dropwise 0.75 M of fresh oxide mesityl and boil 3 hours, selected in the usual way the product connection on Michael without purification was dissolved in a minimum amount of benzene and after the addition of 0.5 ml of piperidine boiled for 1 h, the Solvent is distilled off, the residue is crystallized from butanol.

MP. more than 300oC

Calculated WITH 80,90 N 8,99

Found, From 8.67 N 9,151 IR-spectrum, liquid paraffin: 3460, 1720, 1680, 1100, 870 (with -1)

Study of the biological activity was carried out in the laboratory of pharmacological screening at the Department of organic chemistry EPM. The effect of compounds on blood coagulation was carried out on awake white rats-males weighing 200 to 230, a Blood examination was taken from a vein language and recorded coagulation tests using standard coagulogram N 338 1. Record on paper tape counted the blood clotting time. At the same time conducted a series of experiments in each series of 6 animals) with intraperitoneal introduction 1 ml of physiological solution (control) and ethanol vikasola at a dose of 10 mg/kg

New the initial product is offered /2/ as a comparator drug in the study of coagulation activity.

The results of the experiments are statistically processed /4/ and is shown in the table.

2. Determination of acute toxicity and the calculations were carried out according to the method of Cerberus /3/. White mice weighing 18 to 20 g were injected intraperitoneally 0.5 ml of the suspension of the analyte prepared by adding 1 to 2 drops of tween-80. At each dose in the experience took 6 mice, it was found that the tested substance is more than 870 mg/kg, therefore this substance belongs to the class of practically non-toxic substances.

3. The results of these studies show that the claimed compound has a pronounced hemostatic effect greater than the activity of a drug menadione, being practically non-toxic.

This indicates the feasibility of further studies of this material with the aim of creating effective drug.

20(29)-Lupen-[(2,3:3,4)-5,5-dimethylhexane-2-it]-28-OIC acid formula

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having coagulation activity.

 

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