2-(5-r-aminomethylfuryl-2)-1,3-dioxalanes displaying growth-regulating and anti-stress activity

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to chemistry of biologically active substances, in particular, to novel biologically active compounds, namely, 2-(5-R-aminomethylfuryl-2)-1,3-dioxalanes of the formula (I): wherein at (Ia) R means --Ts and at (Ib) R means -CO-Ph. These compounds show properties as activating agent with respect to germination of winter wheat grains of sort "Pobeda-50" possessing growth-regulating and anti-stress activity.

EFFECT: valuable biological properties of compounds.

1 cl, 2 tbl, 2 ex

 

The invention relates to the field of agriculture and to the chemistry of biologically active substances, to new biologically active compounds of some furan of formula I

Ia R=-Ts; IB R=-CO-Ph,

exhibiting the properties of activator germination of winter wheat varieties Victory-50 with astragalina and anti-stress activity.

To the closest analogs in the structure of the claimed compounds can be classified as 2-(furyl-2)-1,3-dioxolane - plant growth regulator with anti-stress activity [kulenovic VG, Kalashnikov VG, Kosulina SO, Nenko NI, Smolyakov VP 2-Furyl(aryl)-1,3-doxycycline, synthesis, stereochemistry, reaction speed formation, properties and applications // New directions in the chemistry of cyclic acetals. - M.: Chemistry. - 2002].

As similar properties known gibberellins, are widely used to activate germination.

However, the gibberellin - expensive drug microbiological synthesis and inaccessible. In addition, its use causes irrational waste of plastic substances [Muromtsev G.S. and other foundations of chemical regulation of growth and productivity of plants. - M.: Agropromizdat, 1987. - Pp.33-80].

The present invention is the identification of new promising biologically active compounds - 2-(5-R-aminomethylphenol-2)-13-dioxolane formula I - to expand the Arsenal of biologically active substances obtained synthetically, for use in agriculture as growth regulators and anti-stress drugs.

This is achieved by the synthesis of 2-(5-R-aminomethylphenol-2)-1,3-dioxolane I new not previously described compounds containing in their structure of 1,3-dioxolane fragment and is capable, by analogy with the known plant growth regulator - 2-(furyl-2)-1,3-dioxolane - show properties of activators germination of winter wheat.

Compound I was obtained by condensation of etilenglikola 5-R-aminomethylphenol in the presence of ion exchange resin Amberlist 15.

Investigation of the effect of compounds I by sowing qualities of seeds of winter wheat, on the growth and accumulation of dry weight in leaves and determination of the optimal astragalina concentrations showed that compound I in the optimum the growth-activating concentrations improve sowing qualities of seeds of winter wheat varieties Victory 50 and have good anti-stress activity.

Thus, the set of essential features set forth in the claims, allows to achieve the desired result.

The invention is illustrated by the following examples.

Example 1.

Getting 2-(5-R-aminomethylphenol-2)-1,3-dioxolane I.

To a mixture of 0.01 mol is 5-R-aminomethylphenol and 0.01 mol of ethylene glycol in the 100-120 cm 3benzene type ion-exchange resin Amberlist 15 in the amount of 10-15% by weight of furfural and boil with trap Dean-stark controlling the conversion of the source of furfural by TLC. The reaction mixture is cooled. The cation exchange resin is separated by filtration. To the filtrate add 10-15 cm3petroleum ether. The hot solution is passed through a layer of silica gel and then evaporated to 1/3 of the original volume under reduced pressure. After crystallization receive the corresponding dioxolane.

5-(1,3-dioxolane-2-yl)-2-(4-methylphenylsulfonyl)furan (Ia) - white vatoobraznye substance, TPL124-126°C. the Yield 68%.

1H NMR (CDCl3): 2,27 (CH3, s, 3H), 3,95 (CH2(dioxolane), s, 4H), 4,30 (CH2, 2N), of 5.82 (SN, s, 1H), 6,44 (N-4Furd, 1H, J=3,4 Hz), 6,60 (N-3Fur, d, J=3,4 Hz), to 7.64 (o-NAr, DD, J=2.2 Hz, J=8.0 Hz, 2H), 7,26 (m - NAr, DD, J=2.2 Hz, J=8.0 Hz, 2H), 6,13 (NH, c, 1H).

Found for C15H17NSO5: 55,69 N 5,34 N S 4.26 DEATHS 9,90%. Calculated: 55,72 N 5,30 N 4,33 S 9,92%.

5-(1,3-dioxolane-2-yl)-2-phenylcarbonylamino (IB) is a cream coloured powder, TPL103-104°C. the Yield of 63%.

1H NMR (CDCl3): 3,94 (CH2(dioxolane) s, 4H); 4,48 (CH2s, 2H); 5,80 (CH, 1H); 5,97 (N-4Furd, 1H, J=3,4 Hz); 6,21 (N-3Fur, d, J=3,4 Hz); 7,31...to 7.67 (HAr, m, 5H); 8,64 (NH c, 1H).

Found for C15H15NO4: 65,98 N 5,42 N OF 5.17%. Calculated: 65,93 N Of 5.53 N 5,13%.

Example 2

Astragal the tank and anti-stress (resistance of seedlings to drying) activity of compounds I studied the model by laboratory screening, modified by us, in seeds of winter wheat varieties Victory 50.

In the course of research were identified:

- optimal astragulus concentration of the compounds, the effect on the sowing qualities of seeds of winter wheat,

- the growth and accumulation of dry matter in leaves when grown under normal conditions and when exposed to the stress factor (drying seedlings).

To study astragalina and anti-stress activity of the tested compound I was pre-dissolved in acetone and then in the water.

As similar properties used gibberellins, as a similar structure - Furyan in 0,001%of the energy water solutions.

Seeds of winter wheat were soaked in aqueous solutions of drugs for 18 h, and then were germinated in Petri dishes on moist filter paper for three days.

For detection of anti-stress activity of compounds half three seedlings in each case was subjected to drying for one hour, then the germination of all seeds kept in rolls of filter paper for four days,

Experiment was repeated three times. In each replication were used for 50 pieces of seeds.

About optimal growth stimulating concentration of compounds was tried on aggregate indicators such as germination, length and dry weight of seedlings, and apotentially productivity.

Results determination of optimal concentration of compounds and their impact on sowing qualities of seeds are shown in table 1.

The tests have allowed to establish that all tested compounds in the concentration range of 0.01 and 0.0001 wt.% demonstrate the properties of the growth regulators.

Compound Ia in optimal growth stimulating dose of 0.001 wt.% increases the germination energy by 3%, the length of the cane system 7-day-old seedlings by 8.6%, the length of roots seedling - 67.5% and their mass - 31.0 and 78,9%, respectively, and the potential productivity - by 35.6% compared to control.

Compound IB in optimal growth stimulating concentration of 0.001 wt.% no effect on the growth of cane system of seedlings increases the length of the roots - 51.9%, mass cane system - 22.5% root mass on - 71,1%, respectively, and the potential productivity of 43.3% compared to control.

Thus, compound I in the optimum the growth-activating concentrations improve sowing qualities of seeds of winter wheat varieties Victory 50.

The effects of tested compounds on the stability of seedlings of winter wheat varieties Victory-50 to water stress (drying seedlings) are shown in table 2.

The tests have allowed to establish that all tested compounds at optimal concentrations have choir is our anti-stress activity.

Compound Ia in the optimal dose of 0.005 wt.%, increases the length of the cane system 7-days-old seedlings - 24.3%, length of roots seedling - 53,6% and their mass - 36.2 and 100.0% respectively compared to control.

Compound 1B in optimal concentration of 0.0001 wt.% increases the length of the cane system of seedlings by 16.2%, the length of the roots, or by 16.1% and their mass - 36.2 and 63,3% respectively compared to control.

Thus, compound Ia among the tested drugs has the greatest astragalina and anti-stress activity.

The obtained results allow to recommend the compound Ia as a means of increasing the resistance of plants to water stress and improving sowing qualities of seeds of winter wheat varieties Victory 50.

Table 1

Influence of growth regulators on seed quality seed winter wheat varieties Win 50
Version of experienceThe concentration of the aqueous solution, %Germination, %The length of the sproutWeight sproutThe potential productivity
the sproutrootabout the East root
cm± to control, %cm± to control, %mg± to control, %mg± to control, %mg/cm± to control, %
Control - water-9010,9-9,3-7,4-4,2-1,06-
Gibberellins0,0019411,77,39,96,57,96,84,44,81,05-0,1
Furlan0,0019211,77,312,231,28,413,55,326,21,1710,4
Control - acetone0,18610,5-3,67,7-17,27,1-4,1the 3.8-9,51,04-1,9
Compound 1A0,01949,4situated 10.58,814,3 6,7-5,65,134,21,26of 21.2
0,0059610,71,910,738,98,316,95,544,71,2924,0
0,0019311,48,612,967,59,331,06,878,91,4135,6
0,00058911,26,710,435,17,4-of 5.442,11,149,6
0,00019111,37,612,461,18,114,16,673,71,3025,0
Compound 1B0,018911,04,810,840,19,026,86,673,71,4236,5
0,0058910,2-2,99,118,2 8,823,94,621,11,3125,9
0,0019010,2-2,911,751,98,722,56,571,11,4943,3
0,00058610,60,99,928,68,925,45,339,5of 1.3428,9
0,00019111,913,310,436,49,229,66,365,81,3025,0
NDSof 0.951,40,40,50,30,40,01
Pof 0.95,%1,4the 3.8the 4.75,55,13,4
Note:

NSR,95 least significant difference at 5%is the level of significance, P0,95 - error experience, % at 5%level of significance

Table 2

Influence of growth regulators on the stability of winter wheat seedlings of the cultivar Pobeda 50 to water stress
Version of experienceSolution concentration, %The length of the sproutWeight sprout
the sproutrootthe sproutroot
cm± to Pin the roll, %cm± to Pin the roll, %mg± to Pin the roll, %mg± to Pin the roll, %
Control - water07,5-the 5.7-5,6-3,2-
Gibberellins0,0017,95,36,17,05,9of 5.4a 3.9of 21.9
Furlan0,0018,614,76,819,36,18,94,540,6
Control - acetone0,17,4-1,35,6-1,8the 4.7-16,13,0-6,3
Connection0,018,616,25,9of 5.46,640,4the 3.826,7
Ia0,0059,224,38,653,66,436,26,0100,0
0,0019,021,67,228,66,334,04,653,3
0,00058,210,87,025,05,925,5the 4.756,7
0,00018,19,55,5-1,8the 5.721,33,413,3
Connection0,018,312,25,9of 5.46,638,44,446,7
IB0,0058,818,95,6-6,7 42,63,0-
0,0018,514,96,07,16,5to 38.3the 4.756,7
0,00058,19,5a 4.9is 12.56,334,04,136,7
0,00018,616,26,516,16,436,2a 4.963,3
NDSof 0.950,30,50,330,36
Pof 0.95,%3,44,25,6of 5.4

2-(5-R-Aminomethylphenol-2)-1,3-dioxolane formula 1

,

where Ia R=-Ts; IB R=-CO-Ph,

showing astragulus and anti-stress activity.



 

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16 cl, 2 tbl, 185 ex

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27 cl, 2 tbl, 429 ex

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32 cl, 10 tbl, 129 ex

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EFFECT: valuable medicinal properties of compounds and composition.

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EFFECT: improved preparing method, valuable medicinal properties of compounds and composition.

11 cl, 2 tbl

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EFFECT: valuable medicinal properties of compounds and composition, improved method for treatment of infections.

24 cl, 14 tbl, 1 dwg, 45 ex

FIELD: organic chemistry, medicine, oncology, pharmacy.

SUBSTANCE: invention relates to quinazoline derivatives of the formula (I) or their pharmaceutically acceptable salts wherein m = 0 or 1; each group R1 can be similar or different and represents halogen atom, hydroxy- and (C1-C6)-alkoxy-group, or group of the formula Q3-X1 wherein X1 represents oxygen atom (O); Q3 represents phenyl-(C1-C6)-alkyl, heteroaryl-(C1-C6)-alkyl, heterocyclyl or heterocyclyl-(C1-C6)-alkyl, and wherein heteroaryl group represents aromatic 5- or 6-membered monocyclic rings with one or two nitrogen heteroatoms, and any heterocyclyl group defined as the group R1 represents non-aromatic saturated or partially saturated 3-6-membered monocyclic ring with one or two heteroatoms chosen from oxygen and nitrogen atoms, and wherein adjacent carbon atoms in any (C2-C6)-alkylene chain in the substitute R1 are separated optionally by incorporation of oxygen atom (O) in the chain, and wherein any group CH2 or CH3 in the substitute R1 comprises optionally in each of indicated groups CH2 or CH3 one or some halogen substitutes or a substitute chosen from hydroxy-, (C1-C6)-alkoxy-group, (C1-C6)-alkylsulfonyl or pyridyloxy-group, and wherein any heteroaryl or heterocyclyl group in the substitute R1 comprises optionally 1, 2 or 3 substitutes that can be similar or different and chosen from hydroxy-group, carbamoyl, (C1-C6)-alkyl, (C1-C6)-alkoxycarbonyl, N-(C1-C6)-alkylcarbamoyl, N,N-di-[(C1-C6)-alkyl]-carbamoyl, (C1-C6)-alkoxy-(C1-C6)-alkyl and cyano-(C1-C6)-alkyl, or among group of the formula -X5-Q6 wherein X5 represents a direct bond or -CO, and Q6 represents heterocyclyl or heterocyclyl-(C1-C6)-alkyl that comprises optionally (C1-C6)-alkyl as a substitute wherein heterocyclyl group represents non-aromatic, fully or partially saturated 5- or 6-membered monocyclic ring with one or two heteroatoms chosen from nitrogen and oxygen atom; R2 represents hydrogen atom; R3 represents hydrogen atom; Z represents a direct bond or oxygen atom; Q1 represents phenyl, (C3-C7)-cycloalkyl, heteroaryl-(C1-C6)-alkyl, heterocyclyl or heterocyclyl-(C1-C6)-alkyl wherein heteroaryl group represents 5- or 6-membered aromatic monocyclic ring with I, 2 or 3 heteroatoms of nitrogen, and any heterocyclyl group represents non-aromatic fully or partially saturated 5- or 6-membered monocyclic ring with one or two heteroatoms chosen from oxygen, nitrogen or sulfur atom, or when Z represents oxygen atom (O) then Q1 can represent (C1-C6)-alkyl or (C1-C6)-alkoxy-(C1-C6)-alkyl and wherein any heterocyclyl group in the group -Q1-Z- comprises substitutes chosen from (C1-C6)-alkyl, (C1-C)-alkoxycarbonyl and pyridylmethyl, and wherein any heterocyclyl group in the group -Q1-Z- comprises optionally 1 or 2 oxo-substitutes; Q2 represents aryl group of the formula (Ia): wherein G1 represents halogen atom, trifluoromethyl, (C1-C6)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C6)-alkoxy-, (C1-C6)-alkylthio-group, (C2-C6)-alkanoyl, pyrrolyl, pyrrolidinyl, piperidinyl and morpholinomethyl, and each G2, G3, G4 and G5 that can be similar or different represents hydrogen, halogen atom, cyano-group, (C1-C6)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl and (C1-C6)-alkoxy-group, or G1 and G2 form in common group of formulae -CH=CH-CH=CH-, -CH=CH-O- or -O-CH=CH- being each group carries optionally halogen atom as a substitute, or G1 and G2 form in common group of formulae -O-CH2-O- or -O-CH2-CH2-O-, or -O-CH2-CH2-O-, and each among G3 and G4 represents hydrogen atom, and G5 is chosen from hydrogen and halogen atom. Proposed compounds possess anti-tumor activity and designated for preparing a medicine preparation for its using as an anti-tumor agent for suppression and/or treatment of solid tumors. Also, invention relates to a pharmaceutical composition based on abovementioned compounds.

EFFECT: valuable medicinal properties of compounds.

20 cl, 7 tbl, 57 ex

FIELD: organic chemistry, antibacterial agents.

SUBSTANCE: invention relates to a novel heterocyclic compound, in particular, 3-(5-nitrofuryl)-7-(5-nitrofurfurylidene-3,3a,4,5,6,7-hexahydro-2H-indazole of the formula (1): that elicits an antibacterial activity with respect to bacterium of genus Staphylococcus and can be used in medicine. The compound of the formula 91) is prepared by reaction of 2,6-di-(5-nitrofurfurylidene)-cyclohexanone with hydrazine hydrate in propanol-2 medium. The yield is 80%, m. p. at 193-195°C, empirical formula is C16H14N4O6, LD50 value at intraperitoneal administration is 500 mg/kg. This compound exceeds activity of furacilinum and furazolidone by 16 and 2-31 times, respectively. Invention provides preparing compound possessing the higher and selective antibacterial activity and low toxicity.

EFFECT: valuable properties of compound.

1 cl, 3 tbl, 1 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to novel biologically active compounds that act as agonists of arginine-vasopressin V2-receptors. Invention describes a derivative of 4,4-difluoro-1,2,3,4-tetrahydro-5H-benzazepine represented by the general formula (I): or its pharmaceutically acceptable salt wherein symbols have the following values: R1 represents -OH, -O-lower alkyl or optionally substituted amino-group; R2 represents lower alkyl that can be substituted with one or more halogen atoms, or halogen atom; among R3 and R4 one of them represents -H, lower alkyl or halogen atom, and another represents optionally substituted nonaromatic cyclic amino-group, or optionally substituted aromatic cyclic amino-group; R5 represents -H, lower alkyl or halogen atom. Also, invention describes a pharmaceutical composition representing agonist of arginine-vasopressin V2-receptors. Invention provides preparing new compounds possessing with useful biological properties.

EFFECT: valuable medicinal properties of compound and composition.

9 cl, 18 tbl, 13 ex

FIELD: organic chemistry, insecticides.

SUBSTANCE: invention relates to an insecticide-acaricide agent comprising a mixture of compound of the formula (I): wherein X means halogen atom, (C1-C4)-alkyl, (C1-C4)-alkoxyl; W, Y and Z mean independently of one another hydrogen atom (H), halogen atom, (C1-C4)-alkyl, (C1-C4)-alkoxyl; A means H, (C1-C6)-alkyl; B means H, methyl or ethyl; A and B in common with carbon atom to which they are bound form saturated unsubstituted (C3-C6)-ring or substituted with (C1-C4)-alkoxy-group; D means H, (C1-C6)-alkyl; G means H or one of the following groups: (b) or (c) wherein L means oxygen atom (O); M means O; R1 means (C1-C10)-alkyl, (C3-C6)-cycloalkyl that if necessary can comprise one nitrogen atom (N) or O; R2 means (C1-C10)-alkyl and agonist, respectively, antagonist of nicotine acetylcholine receptors chosen from the group comprising compounds of formulas: (IIa) (IIe) (IIg) (IIh) (IIi) (IIk) (IIl) and (IIm) taken in synergetically effective ratio.

EFFECT: valuable biological properties of substances.

6 cl, 22 tbl, 6 ex

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