4-substituted-3-(1-alkyl-2-chloro-1h-indol-3-yl)furan-2,5-diones, synthesis method thereof and use in photochemical generation of stable fluorescent compounds and 4,5-substituted-6-alkyl-1h-furo[3,4-c]carbazole-1,3(6h)-diones, synthesis method thereof and use as fluorophores

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds, specifically to 4-substituted-3-(1-alkyl-2-chloro-1H-indol-3-yl)furan-2,5-diones of general formula I , where R1=H, C1-C6 alkyl; R2=H, C1-C6 alkyl, C1-C6 alkoxy; R3=phenyl, naphthyl, 2-phenyl-1-ethenyl, thienyl, furyl, pyrrolyl, benzothiophenyl, benzofuranyl, indolyl, synthesis method thereof and use as compounds capable of photochemical generation of stable fluorophores of formula II, which can be used, for instance in information storage systems, particularly as photosensitive components of material for three-dimensional recording and storage of information. The invention also relates to novel 4,5-substituted-6-alkyl-1H-furo[3,4-c]carbazole-1,3(6H)diones of general formula II , where R1=H, C1-C6 alkyl; R2=H, C1-C6 alkyl, C1-C6 alkoxy; R4=H, R5=phenyl, R4, R5=benzo, naphtho, thieno, furo, pyrrolo, benzothieno, benzofuro, indolo, method for synthesis of said compounds and use as fluorophores.

EFFECT: obtaining novel compounds and possibility of using said compounds as fluorophores.

14 cl, 2 tbl, 8 ex

 

The invention relates to new compounds, namely 4-substituted-3-(1-alkyl-2-chloro-1H-indol-3-yl)furan-2,5-diones of General formula I

where R1=H, C1-C6alkyl; R2=H, C1-C6alkyl, C1-C6alkoxy; R3=phenyl, naphthyl, phenylethenyl, thienyl, furyl, pyrrolyl, benzothiophene, benzofuranyl, indolyl.

Compound I under irradiation of visible light to generate a stable fluorescent substance (4,5-substituted-6-alkyl-1H-furo[3,4-C]carbazole-1,3(6N)-diones (II).

The invention relates also to a new method for producing 4-substituted 3-(1-alkyl-2-chloro-1H-indol-3-yl)furan-2,5-diones of General formula I.

The invention relates also to the use of 4-substituted-3-(1-alkyl-2-chloro-1H-indol-3-yl)furan-2,5-diones above General formula I as compounds able to photochemical generation of stable fluorophores that can be used, for example, in systems for storing information, in particular, as the photosensitive material components for three-dimensional recording and storing information.

The invention relates to new compounds, namely (4,5-substituted-6-alkyl-1H-furo[3,4-C]carbazole-1,3(6N)-diones of General formula II

where R1=H, C1-C6alkyl; R2=H, C1-C6alkyl, C1- 6alkoxy; R4=N, R5= phenyl, R4,R5= benzo, oil, thieno, furo, pyrrolo, benzothieno, benzofuro, indolo.

The invention relates also to a new method of obtaining (4,5-substituted-6-alkyl-1H-furo[3,4-C]carbazole-1,3(6N)-diones of General formula II.

The invention relates also to the use of (4,5-substituted-6-alkyl-1H-furo[3,4-C]carbazole-1,3(6N)-diones above General formula II, as compounds with fluorescence.

The closest in structure to the compounds of General formula I is (1,2-dimethyl-1H-indol-3-yl)-4-[(1E)-prop-1-enyl]furan-2,5-dione of the formula III

Compound III exhibits photochromic properties (the absorption band of the original form λmax=436 nm, the absorption band of the cyclic form λmax=492 nm) /Tadatsugu Yamaguchi and Masahiro Irie // Chemistry Letters, 2005, Vol.34, No.1, p 64-65/. The method of its production is in the interaction (3E)-3-pentenol acid (1.2-dimethyl-1H-indol-3-yl)(oxo)acetyl chloride, obtained in situ from 1,2-dimethyl-1H-indole.

The closest in structure to the compounds of General formula II is 4-(2-chlorophenyl)-8-(4-hydroxybutyl)-9-methoxy-6-methyl-1H-furo[3,4-C]carbazole-1,3(6N)-dione of the formula IV,

obtained by hydrolysis of 4-(2-chlorophenyl)-8-(4-hydroxybutyl)-9-methoxy-6-methylpyrazolo[3,4-C]carbazole-1,3(NN)-dione, which investigated as Inga is for kinase /Jeff C. Smaill, But N. Lee, Brian D. Palmer, Andrew M. Thompson, Christopher J. Squire, Edward N. Baker, John R. Booth, Alan Kraker, Ken Hook and William A. Dennya, Bioorganic & Medicinal Chemistry Letters 18 (2008) 929-933/.

The technical result of the invention are new compounds in the range of 3-(1H-indol-3-yl)furan-2,5-diones, showing new for this series of compounds properties to generate the action of light stable fluorescent substance.

The technical result of the invention are new compounds in a series of 1H-furo[3,4-C]carbazole-1,3(6N)-diones, showing new for this series of compounds fluorescent properties.

The technical result is achieved by compounds of General formula I, their method of preparation and their use as substances that form when the action of light stable fluorescent compounds II.

The technical result is also achieved by the compounds of General formula II, their method of preparation and their use as fluorescent substances.

The invention satisfies the criterion of inventive step, the proposed new compounds exhibit new properties in a series of structural analogues.

The method of obtaining the compounds of the first lies in the interaction of substituted acetic acids of the General formula R3CH2COOH in the presence of trialkylamine with (2-chloro-1H-indol-3-yl)(oxo)acetylchloride General formula V, which is obtained by processing oxalylamino umestnogo of oxyindole General formula VI,

where R1=H, C1-C6alkyl; R2=H, C1-C6alkyl, C1-C6alkoxy; R3= phenyl, naphthyl, phenylethenyl, thienyl, furyl, pyrrolyl, benzothiophene, benzofuranyl, indolyl.

The method of obtaining the compounds II is cyclization under the action of visible light 4-substituted-3-(1-alkyl-2-chloro-1H-indol-3-yl)furan-2,5-diones of General formula I, where R have the above values, accompanied with evolution of hydrogen chloride.

Below are examples of the preparation of compounds I and II.

Example 1. 3-(2-Chloro-1-methyl-1H-indol-3-yl)-4-phenyl-furan-2,5-dione (R1=CH3, R2=H, R3= phenyl) (Ia).

To a solution of 0.73 g (5 mmol) of 1-methyloxindole in 10 ml of dry 1,2-dichloroethane pin 0,86 ml (10 mmol) of oxalicacid and leave at room temperature for 2 hours. The solvent is then evaporated and the dry residue is poured a solution of 0.5 ml (5 mmol) of phenylacetic acid and 2.1 ml (15 mmol) of triethylamine in 15 ml of dry 1,2-dichloroethane, the mixture is boiled for 2 hours, cooled, the precipitate is filtered off and the mother liquor is distilled off the solvent. The resulting product is washed with methanol, precipitated precipitate is recrystallized from methanol. The product is recrystallized from butanol. Yield 0.35 g (20.7%). Red crystals, TPL 213-214°C. Found, %: C 67.45, H 3.5, N 4.02. For C19H12ClNO3calculated, %: C 67.57, H 3.58, N 4.15.

The infrared spectrum, cm-1: 720 (C-C1), 1760, 1820 (C=O).

An NMR spectrum1H, COCl3, δ, ppm: 3.82 (s, 3H, CH3), 7.02-7.10 (m, 2H, arene), 7.22-7.42 (m, 5H, arene), 7.60-7.65 (m, 2H, arene).

Compounds Ib-d in examples 2-4 are obtained analogously to example 1 using 1-naphthyl-, (E)-2-phenyl-1-ethynyl and 3-tirelessly acids, respectively.

Example 2. 3-(2-Chloro-1-methyl-1H-indol-3-yl)-4-(1-naphthyl)-furan-2,5-dione (R1=CH3, R2=H, R3=1-naphthyl) (Ib).

The product is recrystallized from butanol. Yield 0.42 g (21.7%). Red crystals, TPL 206-207°C. Found, %: C 71.18, H 3.55, N 3.59. For C23H14ClNO3calculated, %: C 71.23, H 3.64, 3.61 N.

The infrared spectrum, cm-1: 720 (C-C1), 1760, 1820 (CO).

An NMR spectrum1N, CDC13, δ, ppm: 3.64 (s, 3H, CH3), 7.00-7.08 (m, 2H, arene), 7.15-7.24 (m, 3H), arene), 7.26-7.34 (m, 1H, arene), 7.35-7.58 (m, 4H, arene), 7,72-to 7.95 (m, 2H, arene).

Example 3. 3-(2-Chloro-1-methyl-1H-indol-3-yl)-4-[(E)-2-phenyl-1-ethynyl]-furan-2,5-dione (R3=CH3, R2=H, R3=(E)-2-phenyl-1-ethynyl) (Ic).

The product is recrystallized from butanol. Yield 0.3 g (16.7 per cent). Orange crystals, TPL 187-189°C. Found, %: C 69.25, H 3.68, N, 3.74. For C21H14ClNO3calculated, %: C 69.33, H 3.88, N 3.85.

The infrared spectrum, cm-1: 720 (C-C1), 1760, 1820 (C=O).

An NMR spectrum1H, CDC13, δ, ppm: 3.88 (s, 3H, CH3), 6.95 (d, 1H, CH), 7.20-7.28 (m, 1H, CH), 7.30-7.42 (m, 5H, arene), 7.45-.54 (m, 3H, arene), 8.08 (d, 1H, arene, J=16.3 Hz).

Example 4. 3-(2-Chloro-1-methyl-1H-indol-3-yl)-4-(3-thienyl)furan-2,5-dione (R1=CH3, R2=H, R3=3-thienyl) (Id).

The product is recrystallized from butanol. Yield 0.23 g (14.7%). Orange crystals, TPL 205-206°C. Found, %: 59.31, H 2.85, N 4.02. For C17H10ClNO3's calculated, %: 59.39, N 2.93, N 4.07.

The infrared spectrum, cm-1: 720 (C-C1), 1760, 1820 (C=O).

An NMR spectrum1N, CDC13, δ, ppm: 3.86 (s, 3H, CH3), 7.08-7.16 (m, 2H, arene), 7.18-7.24 (m, 2H, arene), 7.26-7.48 (m, 2H, arene), 8.24 (m, 1H, arene).

Example 5. Photo product (8-Methyl-1H-benzo[a]furo[3,4-C]carbazole-1,3(8H)-dione) (R1=CH3, R2=H, R4,R5=benzo) (IIa).

Received irradiation for 1 hour heptane solution of compound 1A [0.5 mmol (168.88 mg)] in the quartz photoreactor volume of 0.5 l total light mercury lamps CES-230. The progress of the reaction is controlled by means of UV-spectroscopy. Photo product IIA actively falls out of solution during irradiation in the form of mist. After irradiation, the solvent is evaporated on a rotary evaporator to a volume of 20 ml, the precipitation is filtered off, washed with heptane, dried and weighed. Get 147.2 mg photo product IIA (exit 97.7%). The product is recrystallized from butanol. Yellow crystals, TPL 265-266°C. Found, %: C 68.15, H 4.19, N 6.85. For C19H11NO3calculated, %: 68.24, H 4.23, N, 6.92.

IR spectrum, ν/cm-1: 176, 1820 (C=O).

An NMR spectrum1N, DMSO-d6, δ, ppm: 4.56 (s, 3H, CH3), 7.44 (t, 1H, arene, J=7.5 Hz), 7.68 (t, 1H, arene, J=8.1 Hz), 7.82-7.96 (m, 3H), arene), 8.96-9.12 (m, 3H), arene).

Photoproduct IIb-C in examples 6-8 are obtained analogously to example 5 by irradiation of oil-, phenylethenyl and tienerporno I.

Example 6. Photo product (12-Methyl-5H-furo[3,4-C]oil[2,1-a]carbazole-5,7(12H)-dione) (R1=CH3, R2=H, R4,R5=2,1-oil) (IIb).

Obtained from 3-(2-chloro-1-methyl-1H-indol-3-yl)-4-(1-naphthyl)-furan-2,5-dione (Ib). Exit at 98.27%. Yellow crystals, TPL 270-271°C. Found, %: C 78.55, H 3.68, N, 3.87. For C23H13NO3calculated, %: C 78.62, H 3.73, N 3.99.

The IR spectrum. ν/cm-1: 1760, 1820 (C=O).

An NMR spectrum1N, DMSO-d6, δ, ppm: 4.42 (s, 3H, CH3), 7.40-7.46 (m, 1H, arene), 7.54-7.82 (m, 4H, arene), 8.00-8.20 (m, 2H, arene), 8.78 (d, 1H, arene, J=9.3 Hz), 9.00 (d, 1H, arene, J=7.9 Hz), 9.38 (d, 1H, arene, J=7.6 Hz).

Example 7. Photo product (6-Methyl-5-phenyl-1H-furo[3,4-C]carbazole-1,3(6N)-dione) (R1=CH3, R2=H, R4=H, R5=phenyl) (IIc).

Obtained from 3-(2-chloro-1-methyl-lH-indol-3-yl)-4-[(E)-2-phenylethenyl]furan-2,5-dione (Ic) in hexane. The output of 99.2%. Yellow crystals, TPL 285-286°C. Found, %: C 68.15, H 4.19, N 6.85. For C19H1NO3calculated, %: 68.24, H 4.23, N, 6.92.

IR spectrum, ν/cm-1: 1760, 1820 (C=O).

An NMR spectrum1N, DMSO-d6, δ, ppm: 3.40 (s, 3H, CH3), 7.42-7.52 (t, 1H, arene, J=7.1 Hz), 7.54-7.62 (m, 5H, arene), 7.66-7.82 (m, 3H), arene), 8.86 (d, 1H, arene, J=8.0 Hz)

Example 8. Photo product (11-Methyl-4H-furo[3,4-C]thieno[2,3-a]carbazole-4,6(11H)-dione) (R1=CH3, R2=H, R4,R5=thieno 2,3) (IId).

Obtained from 3-(2-chloro-1-methyl-1H-indol-3-yl)-4-(3-thienyl)-furan-2,5-dione (Id). The output of 98.2%. Yellow crystals, TPL 215-216°C. Found, %: C 66.35, H 2.90, N, 4.45. For C17H9NO3's calculated, %: C 66.44, H 2.95, N 4.5.

The IR spectrum. ν/cm-1: 1760, 1820 (C=O).

An NMR spectrum1H DMSO-d6, δ, ppm: 4.24 (s, 3H, CH3), 7.32-7.42 (m, 1H, arene), 7.50-7.76 (m, 2H, arene), 8.04 (d, 2H, arene, J=5.5 Hz), 8.20 (d, 1H, arene, J=5.5 Hz), 8.76 (d, 1H, J=7.54 Hz, arene).

The obtained compounds were investigated by standard methods, spectral absorption and spectral-fluorescent characteristics in heptane at 293 K.

Electronic absorption spectra were recorded on a spectrophotometer Cary 100" (Varian).

Irradiation of solutions of compounds I spent in a quartz cuvette (l=1 cm) monochromatic light obtained after passing through an interference filter to select the line 436 nm mercury spectrum lamp DRSH-250. The intensity of the incident light, measured by ferrioxalate potassium was 4.24·1015quantum·-1.

Values of the quantum yields of photoreactive was determined by the method described previously / Experimental methods of chemical kinetics, edited by Namamahala, Meglumine, Izd-vo MGU, Moscow, 1985, 384 S./.

Free the fair measurements were conducted on an "Saga Eclipse (Varian). Values of the quantum outputs fluorescence was determined by the method of Parker - Rice /Sparker, Photoluminescence of solutions, Mir, Moscow, 1972, s/using 3-methoxybenzonitrile in toluene (φ=0.1, λthe exposed.=365 nm) as a standard phosphor /Bmikeandvicki, Bambooteen, Organic phosphors. Chemistry, Moscow, 1984, s/.

In tables 1 and 2 list the results of studies of compounds Ia-d /examples 1-4/ and photoproduction IIa-d.

Table 1
Spectral absorption and fluorescence properties of compounds I(a-d) in toluene and quantum yields of photocyclization
No.ConnectionAbsorptionFluorescenceQuantum yield photocyclization
λ-max; nm (ε·103, l·mol-1·cm-1)λmaxnmQuantum yield
Ia440 (8,77)5400,0290,002br/> 0,607*
Ib435 (8,05)5590,0170,224
0,217*
Ic456 (12,83)5540,0610,015
0,03*
Id439 (7,74)5450,0160,235
0,192*
* In heptane.

Table 2
Spectral absorption and fluorescence properties of compounds II(a-d) in toluene and practical outputs of photocyclization
No.ConnectionAbsorptionFluorescenceOutput %
λ-max; nm (ε·103, l·mol-1·cm-1) λmaxnmQuantum yield
IIa436(11,65)
417(11,09)
4660,74897.7
IIb431 (11,30)
418(10,28)
4700,15898.1
IIc364(5,91)
385(5,55)
4630,36598.5
IId393 (6,68)
406(6,60)
4600,05797.0

1. 4-Substituted-3-(1-alkyl-2-chloro-1H-indol-3-yl)furan-2,5-diones of General formula I

where R1= H, C1-C6alkyl; R2=H, C1-C6alkyl, C1-C6alkoxy; R3= phenyl, naphthyl, phenylethenyl, thienyl, furyl, pyrrolyl, benzothiophene, benzofuranyl, indolyl.

2. 4-Substituted-3-(1-alkyl-2-chloro-1H-indol-3-yl)furan-2,5-the ions according to claim 1, where R1= CH3, R2= H, R3= phenyl-3-(1-methyl-2-chloro-1H-indol-3-yl)-4-phenyl-furan-2,5-dione.

3. 4-Substituted-3-(1-alkyl-2-chloro-1H-indol-3-yl)furan-2,5-dione according to claim 1, where R1= CH3, R2= H, R3= 1-naphthyl-3-(1-methyl-2-chloro-1H-indol-3-yl)-4-(1-naphthyl)-furan-2,5-dione.

4. 4-Substituted-3-(1-alkyl-2-chloro-1H-indol-3-yl)furan-2,5-dione according to claim 1, where R1= CH3, R2= H, R3= (E)-2-phenyl-1-ethynyl-3-(1-methyl-2-chloro-1H-indol-3-yl)-4-[(E)-2-phenyl-1-ethynyl]-furan-2,5-dione.

5. 4-Substituted-3-(1-methyl-2-chloro-1H-indol-3-yl)furan-2,5-dione according to claim 1, where R1= CH3, R2= H, R3= 3-thienyl-3-(1-methyl-2-chloro-1H-indol-3-yl)-4-(3-thienyl)furan-2,5-dione.

6. A method of obtaining a 4-substituted-3-(1-alkyl-2-chloro-1H-indol-3-yl)furan-2,5-diones of General formula I according to claim 1, which consists in the fact that the substituted acetic acid of General formula R3CH2COOH, where R3= phenyl, naphthyl, phenylethenyl, thienyl, furyl, pyrrolyl, benzothiophene, benzofuranyl, indolyl, enter into interaction in the presence of trialkylamine with (2-chloro-1H-indol-3-yl)(oxo)acetylchloride General formula V,

where R1= H, C1-C6alkyl; R2= H, C1-C6alkyl, C1-C6alkoxy, which is obtained by processing oxalylamino substituted oxindole General formula VI,

where R1= H, C1 -C6alkyl; R2= H, C1-C6alkyl, C1-C6alkoxy.

7. The use of 4-substituted-3-(1-alkyl-2-chloro-1H-indol-3-yl)furan-2,5-diones of General formula I according to claim 1 as forming substances under the action of visible light fluorescent substance.

8. (4,5-Substituted-6-alkyl-1H-furo[3,4-C]carbazole-1,3(6N)-diones of General formula II
,
where R1= H, C1-C6alkyl; R2= H, C1-C6alkyl, C1-C6alkoxy; R4= H, R5= phenyl, R4,R5= benzo, oil, thieno, furo, pyrrolo, benzothieno, benzofuro, indolo.

9. (4,5-Substituted-6-alkyl-1H-furo[3,4-C]carbazole-1,3(6N)-dione of claim 8, where R1= methyl, R2= H, R4R5= benzo-8-methyl-1H-benzo[a]furo[3,4-C] carbazole-1,3 (8H)-dione.

10. (4,5-Substituted-6-alkyl-1H-furo[3,4-C]carbazole-1,3(6N)-dione of claim 8, where R1= methyl, R2= H, R4R5= oil[2,1]-12-methyl-5H-furo[3,4-C]oil[2,1-a]carbazole-5,7(N)-dione.

11. (4,5-Substituted-6-alkyl-1H-furo[3,4-C]carbazole-1,3(6N)-dione of claim 8, where R1=methyl, R2=H, R4=H, R5= phenyl-6-methyl-5-phenyl-1H-furo[3,4-C]carbazole-1,3(6N)-dione.

12. (4,5-Substituted-6-alkyl-1H-furo[3,4-C]carbazole-1,3(6N)-dione of claim 8, where R1= methyl, R2= H, R4R5= thieno[2,3]-11-methyl-4H-furo[3,4-C]thieno[2,3-a]carbazole-4,6(11N)-dione.

13. The method of obtaining (4,5-substituted-6-alkyl-1H-furo[3,-C]carbazole-1,3(6N)-diones of General formula II according to claim 8, implying the action of visible light on the 4-substituted-3-(1-alkyl-2-chloro-1H-indol-3-yl)furan-2,5-diones of General formula I according to claim 1, where R have the above values.

14. Application (4,5-substituted-6-alkyl-1H-furo[3,4-C]carbazole-1,3(6N)-diones of General formula II according to claim 8 as fluorophores.



 

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SUBSTANCE: invention relates to new N,N-bis(dimethylcarbamoyl)- N,N'-bis(9-anthrylmethyl)hexane-1,6-diamine with formula I:

.

EFFECT: compound has properties of highly-selective and highly-efficient fluorescent chemosensor on Eu3+ cations.

1 cl, 1 dwg, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to new derivatives of 1,2-disubstituted 2-aminobezimidazole, and more specifically to 2-(9-anthrylmethyl)amino-1-[2-(1-pyrrolidinyl)ethyl]benzimidazole of formula I: , which have properties of fluorescent chemosensor on H+ cations.

EFFECT: obtaining new fluorescent chemosensor on H+ cations.

1 dwg, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to new polymer compounds, which can be used as active layers of organic light-emitting diodes with high radiation efficiency in the blue range. New branched polyphenylenes are proposed with general formula (I): , where n - ranges from 10 to 20; R - C1-C10alkyl, C1-C10alkoxy group, with high electroluminescence efficiency. A method is also described for producing polyphenylenes of formula (I), which involves homopolycondensation of 1,3,5-tri(n-bromophenyl)benzene in the presence of catalyst, formed in situ based on nickel chloride, triphenylphosphine, bipyridyl and zinc, in an argon current with subsequent reaction of the reaction product with C1-C10alkyl or C1-C10 alkoxyphenylbromide.

EFFECT: modified polyphenylenes have good optical characteristics compared with known modified polyphenylenes.

3 cl, 4 dwg, 1 tbl, 6 ex

FIELD: physics.

SUBSTANCE: electroluminescent material is described, consisting of an electron injection layer, an active luminescent layer based on a metal chalate complex, a hole transport layer and a hole injection layer. The luminescent substance is in form of new zinc complexes based on sulphonylamino derivatives of 2-phenylbenzoxazole or 2-phenylbenzothiazole. The hole transport layer of the material is preferably a mixture of triphenylamine oligomers.

EFFECT: electroluminescent material with high moisture resistance, high resistance to crystallisation and high thermal stability.

9 cl, 5 ex

FIELD: chemistry.

SUBSTANCE: invention concerns fluorescent bleach containing a mix of two asymmetrically substituted and one symmetrically substituted triazinylaminostilbene disulfone acid, a new symmetrically substituted derivative, method of their obtaining, and application of the mix in synthetic or natural organic material (especially paper) bleaching and in fluorescent bleaching and sun resistance boost of textile.

EFFECT: high substantivity and light resistance of the claimed fluorescent bleaches and their mixes, and better water solubility of the claimed mixes in comparison to the solubility of each individual bleach.

15 cl, 2 tbl, 12 ex

FIELD: chemistry.

SUBSTANCE: polynucleotide is obtained, coding chromo- or fluorescen mutant wild type DsRed (SEQ ID N0:2), where chromo- or fluorescent mutant contains a substitute in the amino acid position 42 SEQ ID N0:2, and optionally one or more substitutes in the amino acid positions, chosen from a group, consisting of 4, 2, 5, 6, 21, 41, 44, 117, 217, 145. Using the polynucleotide in the vector, the host cells which express chromo- or fluorescent mutant DsRed are transformed. The invention allows for obtaining chromo- or fluorescent polypeptide DsRed, which matures faster than wild type DsRed.

EFFECT: increased effectiveness.

26 cl, 10 dwg, 2 tbl, 4 ex

FIELD: chemistry.

SUBSTANCE: invention refers to novel compounds with affinity to MC4 receptors, of the general formula (I): , where A is -CH2- or -C(O)-; R1 is (C1-C8)alkyl; R2 is (C1-C8)alkyl; R3 is radical of the formula -(CH2)s-R'3; R'3 is 5-6-member heterocycloalkyl containing one or two nitrogen atoms and possibly one oxygen atom possibly substituted with (C1-C6)alkyl or benzyl; or radical of the formula -NW3W'3; W3 is hydrogen atom or (C1-C8)alkyl; W'3 is radical of the formula -(CH2)s'-Z3; Z3 is hydrogen atom, (C1-C8)alkyl; s and s' are independently an integer within 0 to 6; B is 5-6-member monocyclic unsaturated, aromatic or non-aromatic radical which can be condensed with 5-6-member unsaturated, aromatic or non-aromatic radical forming bicyclic condensed system, and B is possibly containing one or more equal or different heteroatoms selected out of O, S and N, and possibly substituted with one or more equal or different radicals selected out of halogen atom, nitro group, cyano group, oxy group, -XB-YB and phenyl possibly substituted with one substitute selected out of halogen atom and (C1-C6)alkyl; XB is a covalent bond, -O-, -S-, -C(O)-, -C(O)-O-; YB is (C1-C6)alkyl; or pharmaceutically acceptable salt of claimed compounds.

EFFECT: improved obtainment and application efficiency of compounds for production of drug for treatment of diseases related to MC4 receptor activation.

20 cl, 4 dwg, 2 tbl, 81 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of formula I , where R1 is C1-C7-alkyl; R2 is C1-C7-alkyl, C1-C7-haloalkyl, C3-C8-cycloalkyl; R3 is -NRaRb; possibly substituted phenyl, thiophenyl, furanyl, where the substitutes are selected from a group consisting of halogen, C1-C7-alkoxy, C1-C7-alkylsulphonyl and -C(O)O-C1-C7-alkyl; R4 is hydrogen or C1-C7-alkyl; R5 is hydrogen, halogen, C1-C7-alkyl, phenyl; or R5 together with R4 can form a ring selected from a group consisting of C5-C7-cycloalkyl, tetrahydrofuranyl, piperidine, tetrahydropyran, phenyl or pyridinyl, which can possibly be substituted with -C(O)O-C1-C7-alkyl; Ra and Rb together with the nitrogen atom to which they are bonded form piperidine; and to pharmaceutically acceptable salts thereof. The invention also relates to a medicinal agent based on the said compounds which has GABA-B receptor allosteric enhancement effect.

EFFECT: obtaining novel compounds and a medicinal agent based on the said compounds, which can be used in medicine for treating central nervous system disorders.

13 cl, 42 ex

FIELD: pharmacology.

SUBSTANCE: present invention relates to antagonists of serotonin 5-HT5 receptors with general formula 1 and their pharmaceutically acceptable salts and/or hydrates, particularly to substituted 3-sulphonyl-[1,2,3]triazolo[1,5-a]quinazolines and 3-sulphonyl-thieno[2,3-e][1,2,3]triazolo [1,5-a]pyrimidines, as active compounds for pharmaceutical compositions and medicinal agents, and methods of producing said compounds. In general formula 1 , Ar is a phenyl which is unsubstituted or substituted with halogen or at least one lower alkyl; R1 is a hydrogen atom or optionally substituted amine group, or optionally substituted 5-6 member azaheterocyclyl, bonded by a nitrogen atom to a carbon atom of a triazolopyrimidine ring with 1-2 heteroatoms selected from nitrogen, oxygen or sulphur, and optionally annulated with a benzene ring; where the substitutes are selected from hydrogen, optionally substituted C1-C5alkyl, optionally substituted C3-C8cycloalkyl, alkoxy group, acyl, saturated or unsaturated optionally annulated 5-7 member heterocyclyl, where heteroatoms are selected from nitrogen, oxygen or sulphur, optionally substituted phenyl; R2 and R3 together with carbon atoms to which they are bonded form an optionally substituted benzene or thiophene ring, where substitutes are selected from C1-C5alkyl or halogen atom.

EFFECT: invention also relates to pharmaceutical compositions and medicinal agents, a method of treating or preventing development of CNS diseases mediated by action of serotonin 5-HT5 receptors, for example Alzheimer's disease.

20 cl, 6 dwg, 4 tbl, 8 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to triheterocyclic compound of the formula (I): wherein X represents carbon atom; Y represents carbon or nitrogen atom; W represents carbon or nitrogen atom; U represents -CR2, and Z represents -CR2 or nitrogen atom; ring A represents (C5-C6)-cycloalkyl ring or 5-membered heterocyclic ring comprising one nitrogen, oxygen or sulfur atom; R1 represents alkyl, alkenyl, alkynyl, -NR4R5, -OR6 and others; R3 represents phenyl ring substituted with 1-3 substitutes or pyridyl or 1,3-dioxoindanyl ring substituted with 1-2 substitutes, and its pharmaceutically acceptable salts and pharmaceutical composition containing thereof as an active component. Also, invention relates to derivatives of pyrazolopyrimidine and derivatives of pyrrolopyrimidine. Compounds of the formula (I) show antagonistic activity with respect to corticotropin-releasing factor receptors. The compound can be used in treatment and/or prophylaxis of depression, anxiety state, disorders in food intake, post-traumatic stress, ulcerous disease, irritable bowel syndrome, Alzheimer's disease, abuse in drugs using or alcoholic syndrome dependence.

EFFECT: valuable medicinal properties of compounds and pharmaceutical agent.

7 cl, 1 dwg, 24 ex

FIELD: organic chemistry, biochemistry, medicine, pharmacy.

SUBSTANCE: invention describes a compound of the general formula (I) or (II) wherein R1 represents hydrogen atom; R2 is taken among the group consisting of aryl and heteroaryl; R3 is taken among the group consisting of halogen atom, nitro-, cyano-group, (C1-C6)-alkyl, (C1-C6)-alkoxy-group, trifluoromethyl, trifluoromethoxy-group, -NH2, -NH-(C1-C6)-alkyl and -N-(C1-C6)-alkyl)2; b is a whole number from 0 to 4; R4 is taken independently among the group consisting of halogen atom, hydroxy-, carboxy-, oxo-group, (C1-C6)-alkyl, (C1-C6)-alkoxy-group, (C1-C6)-alkoxycarbonyl, phenyl (wherein phenyl group can be substituted optionally with one-three substitutes taken independently among RD), phenylsulfonyl, heteroaryl (wherein heteroaryl can be substituted optionally with one-three substitutes taken independently among RD), heterocycloalkyl, -NH2, -NHRA, -N-(RA)2,

wherein each RD is taken independently among halogen atom, hydroxy-, carboxy-, oxo-group, (C1-C4)-alkyl, (C1-C4)-alkylthio, hydroxy-(C1-C4)-alkyl, (C1-C4)-alkoxy-group, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl, trifluoromethyl, trifluoromethoxy-group, -NH2. -NHRA, -N-(RA)2, -C(O)N(RA)2, -SO2N(RA)2, acetylamino-, nitro-, cyano-group, formyl, (C1-C6)-alkylsulfonyl, carboxy-(C1-C6)-alkyl and aralkyl; c = 0; a means a whole number from 0 to 1; Y is taken among the group consisting of a residue -(C1-C)-alkyl, -C(O)-, -(C2-C6)-alkenyl)-carbonyl, -carbonyl-(C1-C6)-alkyl)-, -C(S)-, -C(O)NH-(C1-C6)_alkyl), -C(O)-(C3-C7)-cycloalkyl)- and (C3-C7)-cycloalkyl)-C(O)-; represents phenyl;

is taken among the group consisting of phenyl, heteroaryl and cycloalkyl under condition that when R1 represents hydrogen atom, R3 represents hydrogen atom, b = 0, c = 1, Y represents -CH2-, represents phenyl and represents phenyl then R2 is not trimethoxyphenyl, and its pharmaceutically acceptable salts. Also, invention describes a pharmaceutical composition designated for inhibition of activity of phosphodiesterase comprising a pharmaceutically acceptable vehicle and compound by cl. 1, method for preparing pharmaceutical composition, methods for treatment of sexual dysfunction by using compound by cl. 1 or pharmaceutical composition, method for increasing the concentration of cGMP in penis tissue and method for treatment of state when inhibition of activity of phosphodiesterase shows the favorable effect. Invention provides preparing novel compounds possessing useful biological properties.

EFFECT: valuable medicinal and biochemical properties of compounds and composition.

17 cl, 7 tbl, 98 ex

FIELD: organic chemistry, biochemistry, pharmacy.

SUBSTANCE: invention relates to new anellated carbamoyl azaheterocycles of the general formula (1)

or (2) possessing the inhibitory effect on protein kinase activity, a focused library comprising these compounds, and pharmaceutical composition based on thereof. In the general formula (1) or (2) R1 represents hydrogen atom or optionally substituted (C1-C6)-alkyl; R2 and R3 represent independently of one another hydrogen atom, inert substitute, optionally substituted (C1-C6)-alkyl, optionally substituted (C3-C8)-cycloalkyl, optionally substituted phenyl, optionally substituted aryl, optionally substituted heterocyclyl; R4 represents optionally substituted (C1-C6)-alkyl, optionally substituted (C3-C8)-cycloalkyl, optionally substituted phenyl, optionally substituted aryl, optionally substituted heterocyclyl; A and B in common with carbon and nitrogen atoms joined to the form an optionally substituted and optionally condensed azaheterocycle; D and F in common with carbon atoms joined form an optionally substituted and optionally condensed phenyl or aryl, optionally substituted and optionally condensed azaheterocycle. K and L in common with carbon and nitrogen atoms joined to them form an optionally substituted azaheterocycle. Also, invention related to methods for preparing compounds of the general formulae (1) or (2).

EFFECT: improved preparing methods.

10 cl, 2 sch, 25 tbl, 7 ex

FIELD: organic chemistry, chemical technology, pharmacy.

SUBSTANCE: invention relates to new biologically active derivatives of pyridothienodiazepine. Invention describes derivatives of pyridothienodiazepine of the general formula (I):

as a racemate or in form of enantiomers or diastereomers, or their mixture wherein R1 represents hydrogen atom or radical of the formula: R'1-NH-C(Y)- wherein R' represents phenyl radical optionally substituted with one or more similar or different substitutes taken among lower alkyl, lower alkoxy-group, lower alkylthio-group, lower alkoxycarbonyl, lower alkylsulfonyl, halogen atom, trifluoromethyl, trifluoromethyloxy-group, hydroxy-, nitro-, cyano-group, phenyl, phenoxy-group, cycloalkyl or heterocycloalkyl; R2 represents lower alkyl, trifluoromethyl or phenyl radical optionally substituted with one or more similar or different substitutes taken among hydroxy-group, halogen atom, lower alkyl or lower alkoxy-group; X and Y represent independently oxygen (O) or sulfur (S) atom; R3a represents hydrogen atom, lower alkyl, hydroxy-group or radical of the formula -OC(O)R'3a wherein R'3a represents alkyl radical comprising from 1 to 10 carbon atoms optionally substituted with radical of the formula: NR''3aR'''3a wherein NR''3a and R'''3a represent independently hydrogen atom, lower alkyl, phenyl, lower phenylalkyl, alkylcarbonyl or alkoxycarbonyl; R3b represents hydrogen atom or lower alkyl radical; R4 represents radical of the formula: -(CH2)n-CHR'4R''4 wherein n represents a whole number 0, 1, 2, 3, 4, 5 or 6; R'4 and R''4 represent independently hydrogen atom, lower alkyl, cycloalkyl, lower cycloalkylalkyl, phenyl, pyridyl, phenylcarbonyl or adamantyl wherein indicated radicals are substituted optionally with one or more similar or different substitutes taken among hydroxy-group, halogen atom, trifluoromethyl, lower alkyl or lower alkoxy-group; A----B represents -C=N- or -C-N(R5)- wherein R5 represents hydrogen atom, amino-radical, lower alkylamino-group, di-(lower alkyl)-amino-group, cycloalkyl, heterocycloalkyl, guanidyl optionally substituted with nitro- or cyano-group, phenyl optionally substituted with one or more similar or different substitutes taken among alkyl or alkoxyalkyl wherein indicated alkyl or alkoxyalkyl are substituted optionally with oxy- or amino-group; indolyl or radical of the formula: -NH-C(O)-(CH2)c-NH-C(O)(CH2)d-NH2; p represents a whole number 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; c and d represent independently a whole number 0, 1, 2 or 3; or salts of these compounds. Also, invention describes methods for preparing compounds of the general formula (I), pharmaceutical composition based on compounds of the general formula (I) eliciting activity to inhibit binding somatostatin-14 and an intermediate compound of the formula (2) given in the invention description. Invention provides preparing new compounds eliciting useful biological properties.

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

17 cl, 70 ex

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