1-(6'-methoxypropanol-3')-2,2-deacetylation having coagulation activity

 

(57) Abstract:

The inventive sintezirovano new derivative chromone: 1-(6'-methoxypropanol-3')-2,2-deacetylation. The synthesis is carried out by condensation of 6-methoxypropan-3-aldehyde with acetylacetone in pyridine. The compound obtained has 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 proposed connection relates to new derivatives of chromone, namely, substituted (chromosol-3)-tilenum formula:

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Here is the application of a derived chromone, its properties and biological activity not described in literature.

The closest similar in structure and action to the claimed connection is menadione [1]

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

The goal has been achieved by the synthesis of the compounds of formula:

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which is obtained by condensation of 6-methoxypropan-3-aldh (0.01 M) 6-methoxypropan-3-aldehyde in 10 ml of dry pyridine is added 1 ml of acetylacetone and heated on a water bath for 3 hours After cooling, the reaction mixture is poured into ice water, acidified with hydrochloric acid, the precipitate is filtered off and washed with 50% ethanol and water. After recrystallization from acetone obtain 2.5 g (87%) of colorless crystals.

TPL= 137-140oC

Calculated C 67,13 H 4,89

Found,C 66,85 H of 5.05

The IR-spectrum, liquid paraffin: 1705, 1640, 980 (cm-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 200-230 g Blood for the study was taken from the Vienna 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 the introduction of intraperitoneally with 1 ml of physiological solution (control) and standard vikasola at a dose of 10 mg/kg

A new connection at a dose of 10 mg/kg and saline solution and the standard was injected in two doses 24 and 1 h before the start of the experiment. The reference drug is proposed [2] as a comparator drug in the study of coagulation activity.

The results of the experiments B>50carried out according to the method of Cerberus [3] White mice weighing 18-20 g were injected intraperitoneally 0.5 ml of the suspension of the analyte prepared by adding 1-2 drops of tween-80. At each dose in the experience took 6 mice, it was found that LD50the analyte is more than 1025 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.

1-(6'-Methoxypropanol-3')-2,2-deacetylation formula I

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having coagulation activity.

 

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SUBSTANCE: invention provides compounds of general formula I:

, where R1 represents -CO-Ra, -SO2-Rb, or aryl optionally substituted by lower alkoxy, wherein Ra represents cycloalkyl, cycloalkyl(lower)alkyl, cycloalkyloxy, aryl, aryloxy, aryl(lower)alkyl, aryl(lower)alkoxy, aryloxy(lower)alkyl, aryl-S-(lower)alkyl, aryl(lower)alkenyl, provided that aryl group can be optionally substituted by halogen, lower alkyl, hydroxy, nitro, cyano, lower alkoxy, phenyl, CF3, cyano(lower)alkyl, lower alkyl-C(O)NH, lower alkyl-CO, and lower alkyl-S; heteroaryl, heteroaryl(lower)alkyl, or heteroaryl(lower)alkoxy, provided that heteroaryl group is 5- or 6-membered ring or bicyclic aromatic group constituted by two 5- or 6-membered rings including 1-3 heteroatoms selected from oxygen, nitrogen, and sulfur and that heteroaryl group can be optionally substituted by lower alkoxy; Rb represents aryl, aryl(lower)alkyl, or heteroaryl, aryl group optionally substituted by halogen, cyano, or lower alkyl-C(O)NH; R2 and R3 represent hydrogen atoms; R4 representshydrogen or lower alkyl; R5 represents hydrogen, lower alkyl, cycloalkyl, benzodioxyl, or aryl optionally substituted by lower alkyl, halogen, lower alkoxy, hydroxy, or (lower)alkyl-C(O)O; n is 1 or 2; and pharmaceutically acceptable salts thereof and/or pharmaceutically acceptable esters thereof. Invention also provides a pharmaceutical composition exhibiting inhibitory activity with regard to cysteine proteases of the cathepsin family, which composition comprises compound of formula I, pharmaceutically acceptable recipient, and/or adjuvant.

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34 cl, 1 tbl, 13 ex

FIELD: organic chemistry, chemical technology, medicine, biochemistry, pharmacy.

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EFFECT: valuable medicinal properties of compounds.

15 cl, 7 tbl, 56 ex

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