Isopropyl-12-aroyl-2-hydroxy-1,6-dioxo-4-(3-pyridinyl)-7-phenyl-1,3,6,7-tetrahydro-2,5α-methano[1,4]diazepino[1,7α]-quinoxaline-5-carboxylates and method for their preparing

FIELD: organic chemistry.

SUBSTANCE: invention relates to novel individual compounds of series 2,5a-methano[1,4]diazepino[1,7-a]-quinoxaline-5-carboxylates, namely, to isopropyl-12-aroyl-2-hydroxy-1,6-dioxo-4-(3-pyridinyl)-7-phenyl-1,3,6,7-tetrahydro-2,5a-methano[1,4]diazepino[1,7-a]-quinoxaline-5-carboxylates of the formula (1) wherein Ar means phenyl or p-methoxyphenyl, and to a method for their synthesis. Method for synthesis of compound of the formula (1) involves interaction of 3-aroyl-5-phenylpyrrolo[1,2-a]-quinoxaline-1,2,4(5H)-triones with isopropyl-3-amino-3-(3-pyridinyl)-2-propenoate in an inert aprotonic solvent medium and the following isolation of end substances. The proposed method provides synthesis of novel compounds of the formula (1) possessing antibacterial effect with high yield and selectivity.

EFFECT: improved method of synthesis.

4 cl, 1 tbl, 3 ex

 

The invention relates to the field of organic chemistry, namely to new individual compounds of class a 2.5α-methane[1,4]diazepino[1,7-α]chynoxaline-5-carboxylates and method of production thereof, which can be used as starting products for the synthesis of new heterocyclic systems.

Known structural analogues of the claimed compounds obtained by the interaction of 3-aroyl-5-phenylpyrrole[1,2-α]cinoxacin-1,2,4(5H)-Trion 1 alkylamino-5,5-dimethyl-1-cyclohexen-3-areas (Bozdyreva Ks.S., Maslivets A.N., Aliev Z.G. Nucleophilic [3+3]addition dimedone N-alkylimines to pyrrolo[1,2-a]quinoxalme-1,2,4-triones Mendeleev Commun. 2005, No. 4, P.163-164). Synthesis of structural analogues is performed according to the following scheme 1:

where Ar=4-BrC6H4and Alk=CH2CH=CH2(3A) or Ar=4-MeO6H4and Alk=CH2Ph (3b).

The disadvantages of this method include the inability to obtain isopropyl 12-aroyl-2-hydroxy-1,6-dioxo-4-(3-pyridinyl)-7-phenyl-1,3,6,7-tetrahydro-2,5α-methane[1,4]diazepino[1,7-α]cinoxacin-5-carboxylates.

Object of the invention is to develop a simple method of synthesis is not described in the literature isopropyl 12-aroyl-2-hydroxy-1,6-dioxo-4-(3-pyridinyl)-7-phenyl-1,3,6,7-tetrahydro-2,5α-methane[1,4]diazepino[1,7-α]cinoxacin-5-carboxylates.

The task is carried out by boiling 3-aroyl-5-Fenrir the olo[1,2-α ]cinoxacin-1,2,4(5H)-Trion (1A, b) with isopropyl 3-amino-3-(3-pyridinyl)-2-propenoate (2), taken in the ratio 1:1, in an inert aprotic solvent according to the following scheme 2:

where Ar=Ph (1a, 3A) or Ar=p-CH3OS6H4(1B, 3b).

The process is conducted at a temperature 99-101°and the solvent used absolute dioxane.

From the patent and technical literature were not identified ways of getting isopropyl 12-aroyl-2-hydroxy-1,6-dioxo-4-(3-pyridinyl)-7-phenyl-1,3,6,7-tetrahydro-2,5α-methane[1,4]diazepino[1,7-α]cinoxacin-5-carboxylates having similar characteristics with the claimed method, and it has not been used for the original products, solvents in which the reaction takes place, and the temperature, on what basis is it possible to make a conclusion on the compliance of the claimed technical solution the criterion of "novelty" and "inventive step".

The invention is illustrated by the following examples.

Example 1. The 12 isopropyl-benzoyl-2-hydroxy-1,6-dioxo-4-(3-pyridinyl)-7-phenyl-1,3,6,7-tetrahydro-2,5α-methane[1,4]diazepino[1,7-α]cinoxacin-5-carboxylate (3A).

To a solution of 1.8 g (0.0045 mol) of 3-benzoyl-5-phenylpyrrole[2,1-α]cinoxacin-1,2,4(5H)-trione (1A) in 40 ml of absolute dioxane was added a hot solution of 0.94 g (0.0045 mol) of isopropyl 3-amino-3-(3-pyridinyl)-2-propenoate in 30 ml of absolute d is Oksana, boiled for 1.5 h until complete disappearance of the dark purple color of the original compounds (1A), cooled, precipitated precipitate was filtered. Yield 95%. TPL 220-222°C (decomp., from chloroform). The compound (3A)35H28H4About6.

Found, %: C 69.98; N, 4.81; N, 9.30.

Calculated, %: C 69.99; H 4.79; N, 9.33.

Example 2. Isopropyl 2-hydroxy-1,6-dioxo-12-n-methoxybenzoyl-4-(3-pyridinyl)-7-phenyl-1,3,6,7-tetrahydro-2,5α-methane[1,4]diazepino[1,7-α]cinoxacin-5-carboxylate (3b).

To a solution of 1.9 g (0.0045 mol) of 3-n-methoxybenzoyl-5-phenylpyrrole[2,1-α]cinoxacin-1,2,4(5H)-trione (1B) in 40 ml of absolute dioxane was added a hot solution of 0.93 g (0.0045 mol) of isopropyl 3-amino-3-(3-pyridinyl)-2-propenoate in 30 ml of absolute dioxane was heated for 1.5 h until complete disappearance of the dark purple color of the original compounds (1A), cooled, precipitated precipitate was filtered. Yield 87%. TPL 173-5°C (decomp., from chloroform). Compound (3b)36H30N4O7.

Found, %: C at 68.59; H 4.77; N, 8.89.

Calculated, %: C 68.56; H 4.79; N, 8.88.

Compounds (3A, b) is a colourless, crystalline substance, soluble in DMSO and DMF, insoluble in the usual organic solvents, insoluble in water and alkanes; stable when stored under normal conditions.

In the IR spectra of compounds (3A, b), taken in the form of paste in vaseline oil, precuts what are the bands of stretching vibrations of the groups HE and NH in the form of a broad band in the region 3130-3140 cm -1, lactam carbonyl group With1=O and isopropoxycarbonyl group in the field 1716-1720 cm-1, lactam carbonyl group With6=O in the field 1680-1685 cm-1, aroline group in the field 1668-1670 cm-1.

In the spectra of1H NMR of solutions of compounds (3A, b) in DMSO-d6besides the signals of the protons of the aromatic substituents and their associated groups are doublets protons of two methyl groups (0.47-0.48 ppm and 0.72-0.73 ppm) and the proton multiplet (4.48 ppm) isopropyl fragment, the singlet methine proton H12(4.97-5.03 ppm), broadened singlet proton of hydroxyl group (7.33 ppm). From a group of signals of aromatic protons in a strong field (6.32 ppm) is shifted doublet of proton H8, shielded π-electrons of the benzene ring substituent at the nitrogen atom N7and in a weak field - singlet proton H2′(8.45-8.56 ppm) and a doublet of proton H6′(8.59 ppm) pyridine substituent, desecration due to the interaction with the lone-electron pair of the nitrogen atom.

The proposed method is simple, one-step and allows you to get not described in the literature isopropyl 12-aroyl-2-hydroxy-1,6-dioxo-4-(3-pyridinyl)-7-phenyl-1,3,6,7-tetrahydro-2,5α-methane[1,4]diazepino[1,7-α]cinoxacin-5-carboxylates (3A, b) with almost quantitative yields.

When is EP 3. Pharmacological study of isopropyl 12-aroyl-2-hydroxy-1,6-dioxo-4-(3-pyridinyl)-7-phenyl-1,3,6,7-tetrahydro-2,5α-methane[1,4]diazepino[1,7-α]cinoxacin-5-carboxylates (3A, b) in the presence of antimicrobial activity.

Study of antimicrobial activity of compounds (3A, b) was performed by the method of twofold serial dilutions according to the conventional methods (Methods of experimental chemotherapy, edited Hendersen, M., Med., 1971). As the test cultures used the Museum strains: Staphylococcus aureus (St aureus), 906; Escherichia coli (E. Coli), 25922.

Was prepared by serial dilution of the drugs in the nutrient liquid medium. The maximum concentration was 1000 µg/ml or 0.1%. Prepared according to the turbidity standard of microbial suspension (25×104in 1 ml) were introduced into the prepared serial dilution of drugs. After 18-20 hours of incubation at 37°registered inhibitory effect, in 7 days - bactericidal drugs.

Table 1.
The results of the study of antimicrobial activity of compounds 3A, b
ConnectionActivity, ug/ml
St aureus, 906E. Coli 25922
1000.0-<1000.0>500.0-
3b----

Studies have shown (table 1): detected an inhibitory effect of compounds 3A against Staphylococcus aureus at a concentration of 1000.0 μg/ml against Escherichia coli in a concentration of <1000.0>500.0 µg/ml Antibacterial properties in the tested concentrations connection For is not. Compound 3b has no antimicrobial effect at the tested concentrations.

1. Isopropyl 12-aroyl-2-hydroxy-1,6-dioxo-4-(3-pyridinyl)-7-phenyl-1,3,6,7-tetrahydro-2,5α-methane[1,4]diazepino[1,7-α]cinoxacin-5-carboxylates of the formula

where Ar is phenyl or n - methoxyphenyl.

2. The method of obtaining isopropyl 12-aroyl-2-hydroxy-1,6-dioxo-4-(3-pyridinyl)-7-phenyl-1,3,6,7-tetrahydro-2,5α-methane[1,4]diazepino[1,7-α]cinoxacin-5-carboxylates according to claim 1, characterized in that 3-aroyl-5-phenylpyrrole[1,2-α]cinoxacin-1,2,4(5H)-Trion subjected to interaction with isopropyl 3-amino-3-(3-pyridinyl)-2-propenoate in inert aprotic solvent, followed by separation of the desired products.

3. The method according to claim 2, characterized in that the process is conducted at a temperature 99-101°C.

4. The method according to any of claim 2 and 3, distinguished by the different topics as a solvent used absolute dioxane.



 

Same patents:

FIELD: organic chemistry, chemical technology, medicine.

SUBSTANCE: invention relates to new biarylcarboxamides of the general formula (I): wherein A means compound of the formula (II): ; D means oxygen atom (O) or sulfur atom (S); E means a simple bond, oxygen atom, sulfur atom or NH; Ar1 means 5-membered heteroaromatic ring comprising one nitrogen atom (N) and one sulfur atom (S) or one oxygen atom (O), or one S atom, or one N atom; or 6-membered aromatic ring, or heteroaromatic ring comprising one N atom; Ar2 means 5-membered heteroaromatic ring comprising one S atom or on O atom, or one N atom and one O atom, or one N atom; or 6-membered aromatic ring or heteroaromatic ring comprising one N atom; or 9-membered condensed heteroaromatic ring system comprising one O atom, or 10-membered condensed aromatic ring system, or heteroaromatic ring system comprising one N atom wherein aromatic ring Ar2 is possibly substituted with one or two substitutes taken among halogen atom, (C1-C4)-alkyl, cyano-group (-CN), nitro group (-NO2), NR1R2, OR3, trihalogen-(C1-C4)-alkyl, (C1-C4)-acylamino-, hydroxy-, morpholino-, amino-, methylamino-group, amino-(C1-C4)-alkyl and hydroxymethyl but if Ar1-phenyl and Ar2 represent quinolinyl group then Ar2 is substituted with one or two (C1-C4)-alkyls, -CN, -NO2, NR1R2, OR3 wherein R1, R2 and R3 mean (C1-C4)-alkyl and compound of the formula (III) doesn't represent .

EFFECT: improved preparing and treatment methods.

33 cl, 69 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to new individual compounds of azapentacycloeicosanes class. Invention describes 20-aroyl-12-hydroxy-17,17-dimethyl-3-phenyl3,10,13-triazapentacyclo[10.7.1.01,10.O4,9.O14,19]eicosa-4,6,14(19)-2,11,15-triones of the formula:

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

4 cl, 1 tbl, 3 ex

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FIELD: organic chemistry, chemical technology.

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

4 cl, 1 tbl, 3 ex

FIELD: organic chemistry, chemical technology, medicine.

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EFFECT: improved preparing and treatment methods.

33 cl, 69 ex

FIELD: organic chemistry.

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EFFECT: improved method of synthesis.

4 cl, 1 tbl, 3 ex

FIELD: chemistry.

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11 cl, 3 ex, 1 tbl

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13 cl, 2 tbl, 5 ex

FIELD: chemistry.

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EFFECT: obtaining new biologically active compounds and a medicinal composition, based on these compounds, which is a sodium channel inhibitor.

10 cl, 91 ex, 22 tbl

FIELD: chemistry.

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EFFECT: obtaining new compounds with useful biological properties.

55 cl, 421 ex, 1 tbl

FIELD: chemistry.

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EFFECT: obtaining compounds, capable of inhibiting angiogenesis, particularly VEGF production in hypoxic conditions, which can be used as therapeutic means of treating solid malignant tumours.

35 cl, 3 tbl, 147 ex

FIELD: chemistry.

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EFFECT: improved properties.

14 cl, 7 tbl, 20 dwg, 17 ex

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