SU1433005A1 - 2 ,3 ,22s,23s-tetraoxy-24s-ethylcholest-4-ene-on displaying pthytogrowth stimulating activity - Google Patents

Abstract

The invention relates to active steroids, which can be used in agriculture. 2.30, 222.238-tetraoxy-243-g of tilcholesto-4-en-6-one are oxidized by Shch1K-loketone 030, brominated with bromine, dehydrodrobanded by boiling with dimethylformamide in the presence, oxidation by the Nudward method (CH 2 COOH, H, 0; CHjCOOAg, 1), alkaline hydrolysis of con in methanol. The new steroid has an active concentration of 10 M, which gives an extension of the ghpocoile by 75% (hegerspuksin - by 21%) with no inhibitory effect. 1 tsgbl. with “from 00 ate

Description

I It refers to strontium-complete and, in particular, 2g /, E (/, 225,238-tetra-oxy 245-ethnl-cholester-A-en-6-one (compound I) of the formula

to admire phorostimostimuliruyuschee activity.

The aim of the invention is to obtain a new plant growth regulator of brassinosterone plants, surpassing the known natural homobrassinolide (II) compounds in fitorostimuliruyuschy activity, gibba sellin AZ (III) and heteroauxin (IV)

Compound I is prepared from cycloketone (V) according to the following scheme;

 ft.

AcOH

Jli9

AcOAq h- L. AcO

by oxidation of cycloketone (V) with osmium tetroxide, diol (VI) is obtained, which is treated with bromine. The resulting dibromide (VII) is dehydrobromized by boiling in LMFA in the presence of Li-gCOe. The formation of trienone (VIII) under the conditions of the Woodward method is oxidized. At the final stage, mild alkaline hydrogea is carried out and 2g, 3 (, 22S, 238-tetraoxy-248-ethylholest- " and -6 o (T).

O sh

Example, To a solution of 1.50 g (2.80 mmol) of SX 5 cyclo-24B-ethyl-5-cholest-22-ei-6-one (V) in 10 ml of pyridine a solution of 0.524 g (2.06 mmol) is poured osmium tetroxide in 10 ml of pyridine. The mixture of reagents was left overnight, and then treated with a solution of 3.0 g (28.8 p. Total) of sodium sulphite and 0.5 MP (9.31 mmol) of sulfuric acid in 30 nor pitch at 40% MVIH at . Glccmonnuk

ohm mixture; mixture up to cnmnnncg (rtur, BbuninawT nodus; extruded with chloroform. 1fom1 extract; np; pc. with water, evaporated. The residue is slurried onto a slnn-gel column. He is poured with hexium mixture with ether. 0.26 mmol) unreacted cycloketone (V) 0.830 g (1.87 mmol, 91% at 080) 22S, 23S-dioxy-3, 5-cyclo-2145-ethyl-5-cholesan-6- she (VI). Tigr. 160-162 H: (. acetone). Lit.pl. 160-162 S.

To a solution of 1, 448 g (3.26 mmol) of 22S, 235-dioxy-3 {, 5-1C1-clo-45-ethyl-5-cholestan-6-one. (Vi) in 25% acetic acid, 0.2 ml (3.93 mmol) of bromine in 10 ml of acetic acid is added dropwise when distilling. The mixture is incubated for 10 shn at room temperature, vishivaya in water, extracted with chloroform. The extract is washed with a saturated sodium sulfite solution, passed through a layer of silica gel, and evaporated. Get

1.358 g (2.25 mmol, 87%) of 22S-23S-diox-3, (- dibrom-2AS-ethyl-V-x-lestan-b-she (VII). So pl. 172-t75 C (hexane -acetone).

A mixture of 1.318 g (2.18 mmol) of 22S, 235-dioxy-3 / b, 5o -dibrom-2 4S-ethyl-5c-chlostane-6-one (VII) and 2.0 g (27.0 mmol) of carbonate The lithium is boiled under reflux in 30 ml of dimethylformamide for 20 minutes, then cooled to room temperature, drunk in water, extracted with rloroform. The extract is washed with water, passed through silica gel, evaporated. The residue is applied to a silica gel column. Elute with a mixture of hexane and ether (1: 1). P, 704 g (1.59 mmol, 73%) of 225,233-1 cyoxy-248-ethylcholesta-2,4-die-6- per (VIII) is obtained.

To a solution of 0.270 g (0.61) of 225.238-dioxy-2A5-ethyl-cholesta-2,4-cyen-6-one (VIII) in 25 ml of acetic acid and 2 ml of water at 50-55 ° C are added 0.300 g ( 1.81 mmol) silver acetate, then with vigorous stirring 0.170 g (0.67 mmol) of iodine. The reaction mixture is stirred at this temperature for another 20 minutes, then evaporated. The residue is transferred to a separatory funnel, extracted with chloroform. The extract is passed through a layer of silica gel, evaporated, applied to a column with silmklelet. Elu rut

ten

five

0

five

0

five

0

five

0

five

ether, Po.CH V4, n, l / S g- (G), 3

55%) ZCh-l () K -H-2i, 22S-23I-rpiKMa-n-2 / 4Y-eti.X (1L {: gm-4- (H -6-oi (GC).

A solution of n, 1 iO g (0.27 ft.) Aietoxy - 2c, 22I, 23I-pyRX11-2 4; -til - cholest - 4-ei-6-one (IX) and 0.2 g (3.6 mmol) hydr (1 pxy potassium in 20 ml of methanol under reflux for 5, then cooled to room temperature, a silica gel layer was passed through the evaporator, the residue was applied to a silica gel column, and eluted with ether: ethanol (25: 1). TeT-raoxy-245-et shcholest-4-en-6-one (I).

The structure of the compounds obtained was confirmed by spectral data from.

The biological (phyroostatus inhibitory) activity of 2-, 3, 22S j 238-tetra-oxy-245-ethyl-cholest-4-e11-6-one (I) has been investigated in laboratory conditions using beans. To compare the biological activity of the studied compound, the phytohormones gibberellin (III) and heteroaxies (IV) were used, as well as the structural analogue, the natural plant growth regulator — homobrss chelide (II).

Seeds are faso; w are silenced in the solutions of the studied substances of different concentration. In one Petri dish put on the U seed beans and bring on

10 ml of solutions. After a day iabuh- needle seeds are planted in stlklichpki with soil, repetition of experiments 4-fold. Laln germination and growth of seedlings occur at a 12-hour photoperiod with artificial light. After 7 days of growth, the lengths of the hypocotyls and the epicotyls of the treated plants are measured.

The measured data are presented in the table.

From the data shown in the table, it can be seen that the proposed soy :: dynenie has a noticeable stigulatory effect on the growth of flsoli plants. The most effective was concentrated.

The radiation of 10 M. Thus, at this concentration, the elongation of 1% boils by 75% is observed, whereas go.teroauxin under similar conditions stimulates elongation by homoGfassinolide (II) - by 8% and gibberellia (III) - nl 4%. The advantages of compound I should also include the absence of angles

non-melting effect in all studied concentrates, which makes it difficult to use known plant growth stimulants.

Thus, compound (I) possesses growth-stimulating activity, caused by the action of known phytohormones.

Claims (1)

Invention Formula 2 (/, Zo, 223,233-Tetroxy-243-ethyl-x-six-4-en-6 he formula Influence of phytohormones on rdst of bean plants possessing phyrostrostimulating activity. .