1-substituted-3-[(1e)-1-alkenyl]-4-(5-alkoxy-1,2-dimethyl-1h-indol-3-yl)-1h-pyrrole-2,5-diones and use thereof as fluorescent photochromes

FIELD: chemistry.

SUBSTANCE: invention relates to novel 1-substituted-3-[(1E)-1-alkenyl]-4-(5-alkoxy-1,2-dimethyl-1H-indol-3-yl)-1H-pyrrole-2,5-diones of general formula

, where R1=C1-C6alkyl, R2=C1-C6 alkyl, R3=CH2C6H5, C6H5.

EFFECT: obtaining novel compounds which can be used as fluorescent photochromes.

4 cl, 1 tbl, 2 ex

 

1-Substituted-3-[(1E)-1-alkenyl]-4-(5-alkoxy-1,2-dimethyl-lH-indol-3-yl)-1H-pyrrole-2,5-diones and their use as fluorescent photochromes.

The invention relates to new compounds, namely 1-substituted 3-[(1E)-1-alkenyl]-4-(5-alkoxy-1,2-dimethyl-1H-indol-3-yl)-1H-pyrrole-2,5-diones of General formula

,

where R1=C1-C6alkyl, R2=C1-C6alkyl, R3=CH2With6H5With6H5.

Compounds (I) are photochromic and fluorescent properties.

The invention relates also to the use of 1-substituted-3-[(1E)-1-alkenyl]-4-(5-alkoxy-1,2-dimethyl-1H-indol-3-yl)-1H-pyrrole-2,5-diones of the above General formula I as fluorescent fotochrome, which can be used, for example, in systems storing and processing information, in particular as a photosensitive material components for three-dimensional recording and storage of information, and can also be used to create the element base for molecular computers, in particular as molecular switches.

The closest in performance and the achieved result is 3-[(1E)-1-alkenyl]-4-(5-alkoxy-1,2-dimethyl-1H-indol-3-yl)-2,5-furandione (II)

,

where R1=C1-C6alkyl, R2=C1-C6alkyl,

<> exhibiting photochromic properties (absorption band of the original forms λmax=443-445 nm, the absorption band of the cyclic forms λmax=528-530 nm)and fluorescent properties of the original forms with the quantum outputs φ=0.07-0.09. //Metelitsa A.V., Rybalkin VP, Levchenko PV, Makarova N, the Value VA, Minkin V.I. // 3-(5 alkoxy-1,2-dimethyl-1H-indol-3-yl)-4-[(1E)-ALK-1-enyl]furan-2,5-diones and their use as fluorescent photochromes. Patent RU 2314304, 10.01.2008.

The task of the invention are new compounds in a series of heterocyclic 3-(1H-indol-3-yl)-2,5-diones, exhibiting photochromic properties, as well as manifesting in the original acyclic isomer form simultaneously fluorescent properties with high quantum yields.

The technical result of the invention are new compounds in a series of heterocyclic 3-(1H-indol-3-yl)-2,5-diones, exhibiting fluorescent properties with higher quantum yields.

The technical result is achieved by compounds of General formula I and their use as fluorescent photochromes.

The invention satisfies the criterion of inventive step, since it is not known the effect of the nature of the heterocycle in a series of heterocyclic 2,5-diones by the value of the quantum yield.

The method of obtaining the compounds of the first lies in the interaction of 3-[(1E)-1-alkenyl]-4-(5-Ala is XI-1,2-dimethyl-1H-indol-3-yl)-2,5-furandione with amines in the presence of N,N-dimethyl-4-aminopyridine.

Below are examples of making connections.

Example 1. 1-Phenyl-3-(5-methoxy-1,2-dimethyl-1H-indol-3-yl)-4-[1(S)-1-propenyl]-1H-pyrrole-2,5-dione (R1=R2=CH3, R3=C6H5).

To a solution of 0.14 g (0.46 mmol) of 3-(5-methoxy-1,2-dimethyl-1H-indol-3-yl)-4-[(1E)-1-propenyl]-2,5-furandione and 2 mg of N,N-dimethyl-4-aminopyridine in 5 ml of isopropyl alcohol is poured 0.05 ml (0.55 mmol) of aniline and boil 20 minutes. The reaction mixture is cooled, the solvent is distilled off. The residue is purified column chromatography on silica gel (eluent: chloroform). The yield of the target product 0.1 g (58.8%). Orange crystals, TPL 189-191°C. Found, %: C 75.31, H 6.26, N, 6.69. For C26H26N2O3calculated, %: C 75.34, H 6.32, N 6.76.

The infrared spectrum, cm-1: 1690 (C=O).

Range1H NMR, CDCl3, δ, ppm: 1.90 (d, 3H, J=6.7 Hz, CH3), 2.48 (s, 3H, CH3), 3.75 (s, 3H, CH3), 3.80 (s, 3H, CH3), 6.26-6.32 (m, 1H, CHarene), 6.78-6.96 (m, 2H, CHarene), 6.18-6.24 (m, 1H, CHarene), 7.06-7.62 (m, 7H, CHarene). Found, %: C 75.31, H 6.26, N, 6.69. For C26H26H2O3calculated, %: C 75.34, H 6.32, N 6.76.

Compound I of example 2 are obtained analogously to example 1 using 3-[(1E)-1-butenyl]-4-(5-methoxy-1,2-dimethyl-1H-indol-3-yl)-2,5-furandione and benzylamine.

Example 2. 1-Benzyl-3-[1(S)-butenyl]-4-(5-methoxy-1,2-dimethyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione(Rsub> 1=C2H5, R2=CH3, R3=CH2With6H5). The yield of 0.13 g (68.4%). Red crystals, TPL 104-106°C. Found, %: C 75.31, H 6.26, N, 6.69. For C26H26N2O3calculated, %: C 75.34, H 6.32, N 6.76.

The infrared spectrum, cm-1: 1690 (C=O).

Range1H NMR, CDCl3, δ, ppm: 1.00 (t, 3H, j=6.58 Hz, CH3), 2.20 (quintet, 2H, j=7.22 Hz, CH2), 2.40 (s, 3H, CH3), 3.72 (s, 3H, CH3), 3.80 (s, 3H, CH3), 4.78 (s, 2H, CH2), 6.18-6.24 (m, 1H, CH), 6.78-6.90 (m, 2H, CH, arene), 7.06-7.20 (m, 2H, arene), 7.22-7.50 (m, 5H, arene).

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

Electronic absorption spectra were recorded on a spectrophotometer "the Saga of 100 (Varian).

The solutions were irradiated with filtered light mercury lamps DRSH-250 in a quartz cuvette (1=1 cm).

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

The table shows the results of the research connections use the am 1-2 /connections 1-2/. For comparison, the table also contains the results for the prototype 3-(5-methoxy-1,2-dimethyl-1H-indol-3-yl)-4-[(1E)-1-propenyl]-2,5-furandione /connection 3/, taken from the patent RU 2314304.

No.ConnectionThe original form, AndPhotoinduced form, In
AbsorptionFluorescenceAbsorption
λmaxnm (ε·103, l·mol-1·cm-1)λmaxnmQuantum yieldλmaxnm
1.
452 (6.9)5330.13520
2.
451 (9.05)5270.13520
3.
443 (8.8)5240,09530

The compounds obtained in the acyclic form A. the irradiation of solutions of these compounds /form A/ in the bands of their long-wavelength absorption (λmax=451-452 nm) is observed staining, accompanied by the appearance of absorption bands with maxima in the region of 520 nm, indicating the formation of cyclic isomers Century Under irradiation in the absorption bands of the forms In reverse photoreactive recyclization b→a, bringing the system to its original state. Isomeric forms of the a and b thermally stable /after termination of irradiation, the content of the forms a and b does not change with time at elevated temperatures. That is, the compounds exhibit photochromic properties and possess the property of bistability is the ability to exist in two stable, due to structural conditions.

The compounds in its acyclic form And exhibit fluorescent properties.

As can be seen from the table, the compounds 1-2 compared to compound 3 have higher values of the quantum outputs fluorescence isomeric forms A. Quantum yields of fluorescence of isomers for compounds 1-2 1.4 times greater than that described for compound 3.

1. 1-Substituted-3-[(1E)-1-alkenyl]-4-(5-alkoxy-1,2-dimethyl-1H-indol-3-yl)-1H-pyrrole-2,5-diones of General formula
,
where R1=C1-C6alkyl, R2=C1-C6alkyl, R3=CH2With6H5With6H5.

2. 1-Substituted-3-[(1E)-1-alkenyl]-4-(5-alkoxy-1,2-dimethyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione according to claim 1, where R1=R2=CH3, R3=C6H5-1-phenyl-3-(5-methoxy-1,2-dimethyl-1H-indol-3-yl)-4-[(1E)-1-propenyl]-1H-pyrrole-2,5-dione.

3. 1-Substituted-3-[(1E)-1-alkenyl]-4-(5-alkoxy-1,2-dimethyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione according to claim 1, where R1=C5H5, R2=CH3, R3=CH2With6H5-1-benzyl-3-[(1E)-1-butenyl]-4-(5-methoxy-1,2-dimethyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione.

4. P is the physical alteration as fluorescent fotogramas 1-substituted-3-[(1E)-1-alkenyl]-4-(5-alkoxy-1,2-dimethyl-1H-indol-3-yl)-1H-pyrrole-2,5-diones of General formula
,
where R1=C1-C6alkyl, R2=C1-C6alkyl, R3=CH2With6H5With6H5.



 

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31 cl, 7 dwg, 152 ex

FIELD: medicine.

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2 dwg, 2 ex

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10 cl, 1 tbl, 33 ex

Novel insecticides // 2379301

FIELD: chemistry.

SUBSTANCE: compounds with formula I are described, where each of E and Z is oxygen; A is C1-C6alkylene or a 3-member monocyclic ring system, which can be monosubstituted; Y is C1-C6alkylene; p equals 0; q equals 0 or 1; B represents a 3- or 4-member ring system which is completely or partially saturated and can contain a heteroatom selected from oxygen, possibly substituted; each R1 independently represents halogen, nitro group, C1-C6alkyl; or each R1 independently represents an amino group; n equals 1, 2; each of R2 and R3 represents hydrogen; D represents a group and agronomically acceptable salts of said compounds. Also described is a method of producing formula I compounds, intermediate compounds, a pesticide composition containing a formula I compound, as well as an insect control method and a method of protecting plant propagation material.

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16 cl, 8 tbl, 19 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds with general formula (I), where W is oxygen or sulphur; X1 and X3 are independently hydrogen or C1-C6-alkoxy; X2 is hydrogen, halogen, C1-C6-alkyl or C1-C6-alkoxy and X4 is hydrogen, Y is in position (N2) or (N3); when Y is in position (N2), Y is C1-C6-alkyl, C1-C6-fluoroalkyl, phenyl, pyridinyl or pyrazinyl; when Y is in position (N3), Y is phenyl, pyridinyl or pyrimidinyl, where phenyl is optionally substituted with one or more atoms or groups selected from halogen, C1-C5 alkyl, C1-C6-alkoxy; the bond in position C4-C5 is a single or double bond; R1 and R2 each independently represent phenyl and C1-C6-alkyl, where at least one of R1 and R2 represents C1-C6-alkyl; or R1 and R2 together with the nitrogen atom to which they are bonded form a cyclic group containing from 4 to 7 links and a nitrogen atom and possibly another heteroatom, such as nitrogen or oxygen, possibly substituted with one or more C1-C6-alkyl groups; or to their pharmaceutically acceptable salts. The invention also relates to methods of producing the proposed compounds with formula (I), and specifically to compounds with formulae (Ia) and (Ib), in which X1, X3, X3, X4 and Y are as described in general formula (I). The invention also relates to intermediate compounds of synthesis of formula (I) compounds - compounds with formulae (Va) and (Vb). In formula (Va) X1, X3 and X4 represent hydrogen; X2 is hydrogen, halogen or C1-C6-alkoxy and Y is C1-C6-alkyl, C1-C6-fluoroalkyl, phenyl, pyridinyl or pyrazinyl; where phenyl is possibly substituted with one or more atoms or groups selected from halogen, C1-C6-alkyl, C1-C6-alkoxy. In formula (Vb) X1 and X3 represent hydrogen or C1-C6-alkoxy; X2 is hydrogen, halogen, C1-C6-alkyl or C1-C6-alkoxy, X4 is hydrogen; Y is phenyl, pyridinyl or pyrmidinyl; phenyl is possibly substituted with one or more atoms or groups selected from halogen, C1-C6-alkyl, C1-C6-alkoxy. The invention also relates to a medicinal agent based on a formula (I) compound or its pharmaceutically acceptable salt for preventing and treating pathologies where peripheral type benzodiazepine receptors take part. The invention also relates to use of formula (I) compounds in preparing the said medicinal agent and to a pharmaceutical composition for preventing and treating pathologies in which peripheral type benzodiazepine receptors take part.

EFFECT: new compounds have useful biological activity.

11 cl, 3 tbl, 6 ex

.

FIELD: chemistry.

SUBSTANCE: proposed phosphodiesterase 4 inhibitors are characterised by formulae II, III, V, VI, where X is CH or N; L is a single bond, -(CH2)nCONH-, -(CH2)nCON(CH2CH3)-, (CH2)nSO2, (CH2)nCO2 or alkylene, optionally substituted oxo or hydroxy; n assumes values from 0 to 3; R1 is optionally substituted alkyl; R3 - H, alkyl, cycloalkyl, alkoxyalkyl, optionally substituted phenyl, phenylalkyl, heterocyclyl, heterocyclylalkyl or cycloalkylalkyl; R4 and R5 represent alkyl; R6 - cycloalkyl, R7 is H; R8 is H, carboxy, alkoxycarbonyl, -CO-alkyl, optionally substituted alkyl.

EFFECT: new phosphodiesterase 4 inhibitors have improved properties.

55 cl, 30 ex

FIELD: organic chemistry, biochemistry, pharmacy.

SUBSTANCE: invention relates to new compounds of the formula (I):

eliciting inhibitory activity with respect to metalloproteinases and wherein R1 means phenoxy-group wherein phenyl residue can be substituted with one or some halogen atoms, hydroxy-, (C1-C6)-alkoxy-group, (C1-C6)-alkyl, cyano- or nitro-group; R2 means pyrimidine, pyrazine or its N-oxide or phenyl substituted with -SO2NR3R4 wherein R3 and R4 can be similar or different and mean hydrogen atom, direct-chain or branch-chain (C1-C6)-alkyl that can be substituted once or some times with the group OH, N(CH3)2, or it can be broken by oxygen atom, or it represents COR5 wherein R5 means (C1-C)-alkyl group that can be substituted with NH2. Also, invention relates to a pharmaceutical composition comprising above said compounds.

EFFECT: valuable biochemical properties of compounds and composition.

5 cl, 1 sch, 1 tbl, 10 ex

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