Method for methyl n-[3,4-dialkyl-5-(n-methoxy-n-oxoalkyl)-2-furyl] alkanoates production

FIELD: chemistry.

SUBSTANCE: invention relates to a method for methyl n-[3,4-dialkyl-5-(n-methoxy-n-oxoalkyl)-2-furyl]alkanoates production by the general formula where R = C2H5, C3H7, C4H9; R'=(CH2)nCOOCH3, n=5, 6, by reaction of dialkyl acetylenes of the general formula R-C≡C-R, where R=C2H5, C3H7, C4H9, with carboxylic acid esters in the presence of magnesium (Mg, powder) and Cp2TiCl2 catalyst with methyl esters α,ω-dicarboxylic acids CH3CO2(CH2)nCO2CH3, where n=5, 6, at the molar ratio of RC≡CR : CH3CO2(CH2)nCO2CH3:EtAlCl2 : Mg:Cp2TiCl2 = 10:20(50-70):40:(1.8-2.2) in tetrahydrofuran under argon atmosphere at 60°C and atmospheric pressure during 4-8. Methyl n-[3,4-dialkyl-5-(n-methoxy-n-oxoalkyl)-2-furyl]alkanoates (1) yield is 54-76%.

EFFECT: compound are important as initial synthons for biologically active compounds creation for medical and agricultural purposes, exhibiting antibacterial, antiviral, anti-inflammatory, antifungal, antitumor, analgesic, anticonvulsant properties.

1 tbl, 1 ex

 



 

Same patents:

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to compounds of formula (I) and their pharmaceutically acceptable salts, wherein A is thiazolyl, oxazolyl, thienyl, furyl, imidazolyl, pyrazolyl or oxadiazolyl (structures of which are presented in cl.1 of the patent claim), R1 represents C1-6alkyl; R2 represents (i) phenyl substituted by halogen; C1-6alkyl optionally substituted by morpholine or C1-6dialkylamino; C1-6alkoxy optionally substituted by halogen; or heterocyclyl, wherein a heterocyclyl substitute is specified in morpholine; pyrazolyl optionally substituted by C1-6alkyl; piperidinyl; pyrrolidinyl; oxadiazolyl substituted by C1-6alkyl; furyl substituted by C1-6alkyl; dioxydoisothiazolidinyl; triazolyl; tetrazolyl substituted by C1-6alkyl, tridiazolyl substituted by C1-6alkyl; thiazolyl substituted by C1-6alkyl; pyridyl; or pyrazinyl; (ii) substituted or unsubstituted heterocyclyl specified in quinolinyl; pyridyl substituted by C1-6alkoxy or morpholinyl; or benzo [d] [1, 2, 3] triazolyl substituted by C1-6alkyl; R3 represents phenyl substituted by 2 or 3 substitutes specified in halogen; C1-6alkyl; C1-6alkoxy optionally substituted by halogen; hydroxy group; cyano; or -C(=O)ORa, wherein Ra represents phenyl; R4 represents hydrogen, C1-6alkyl or C1-6halogenalkyl. The invention also refers to a pharmaceutical composition containing the compounds of formula (I), a method for PDE10 inhibition, a method of treating neurological disorders, and to intermediate compounds: 2-(4-chlor-3,5-dimethoxyphenyl)furan and 4-(5-methyl-1,3,4-thiadiazol-2-yl)benzaldehyde.

EFFECT: compounds of formula (I) as PDE10 inhibitors.

39 cl, 13 ex, 2 tbl, 77 dwg

FIELD: chemistry.

SUBSTANCE: invention relates to novel labdane-type 6-hydroxynaphthoquinones of formula: where R1=R2=H (Ia); R1=Me, R2=H (1b); R1=H, R2=CO2Et (Ic), which are capable of inhibiting growth of human tumour cells. The most active substance - (lS,4aS,8aR)-methyl 5-{2-[2-(6-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-8-yl)-furan-3-yl]ethyl}-1,4a,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene-1-carboxylate (Ia) inhibits growth of tumour cells CEM-13, U-937 and MT-4 in concentrations of 3.4, 5.8 and 4.3 mcM, respectively. The compounds are obtained from lambertian acid contained in the sap and needles of Siberian cedar.

EFFECT: improved method.

1 cl, 4 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to novel labdane-type 6-hydroxynaphthoquinones of formula: where R1=R2=H (Ia); R1=Me, R2=H (1b); R1=H, R2=CO2Et (Ic), which are capable of inhibiting growth of human tumour cells. The most active substance - (lS,4aS,8aR)-methyl 5-{2-[2-(6-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-8-yl)-furan-3-yl]ethyl}-1,4a,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene-1-carboxylate (Ia) inhibits growth of tumour cells CEM-13, U-937 and MT-4 in concentrations of 3.4, 5.8 and 4.3 mcM, respectively. The compounds are obtained from lambertian acid contained in the sap and needles of Siberian cedar.

EFFECT: improved method.

1 cl, 4 ex, 1 tbl

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to compounds of formula (I) and their pharmaceutically acceptable salts, wherein A is thiazolyl, oxazolyl, thienyl, furyl, imidazolyl, pyrazolyl or oxadiazolyl (structures of which are presented in cl.1 of the patent claim), R1 represents C1-6alkyl; R2 represents (i) phenyl substituted by halogen; C1-6alkyl optionally substituted by morpholine or C1-6dialkylamino; C1-6alkoxy optionally substituted by halogen; or heterocyclyl, wherein a heterocyclyl substitute is specified in morpholine; pyrazolyl optionally substituted by C1-6alkyl; piperidinyl; pyrrolidinyl; oxadiazolyl substituted by C1-6alkyl; furyl substituted by C1-6alkyl; dioxydoisothiazolidinyl; triazolyl; tetrazolyl substituted by C1-6alkyl, tridiazolyl substituted by C1-6alkyl; thiazolyl substituted by C1-6alkyl; pyridyl; or pyrazinyl; (ii) substituted or unsubstituted heterocyclyl specified in quinolinyl; pyridyl substituted by C1-6alkoxy or morpholinyl; or benzo [d] [1, 2, 3] triazolyl substituted by C1-6alkyl; R3 represents phenyl substituted by 2 or 3 substitutes specified in halogen; C1-6alkyl; C1-6alkoxy optionally substituted by halogen; hydroxy group; cyano; or -C(=O)ORa, wherein Ra represents phenyl; R4 represents hydrogen, C1-6alkyl or C1-6halogenalkyl. The invention also refers to a pharmaceutical composition containing the compounds of formula (I), a method for PDE10 inhibition, a method of treating neurological disorders, and to intermediate compounds: 2-(4-chlor-3,5-dimethoxyphenyl)furan and 4-(5-methyl-1,3,4-thiadiazol-2-yl)benzaldehyde.

EFFECT: compounds of formula (I) as PDE10 inhibitors.

39 cl, 13 ex, 2 tbl, 77 dwg

FIELD: chemistry.

SUBSTANCE: invention relates to organic synthesis, specifically to method of production of 5-hydroxyl methyl furfural (5-GMF) using hydrolysis-dehydration of cellulose in aqueous medium at temperature not exceeding 180 °C in presence of mesoporous carbon material “Sibunit”, processed by oxidation of wet air mixture at temperatures higher than 400°C. 5-hydroxyl methyl furfural is promising raw material and is used for production of food additives, pharmaceutical preparations, polymer materials, liquid fuel and fuel additives.

EFFECT: technical result of such method is simple procedure for treatment of mesoporous carbon material “Sibunit”, reduction of environmental risks due to usage of non-toxic oxidizer and absence of washing procedure of catalyst from unreacted sulphuric acid.

1 cl, 1 tbl, 5 ex

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry - obtaining derivatives of 3-furylpropane-1-on derivatives of formula 1a-j, where R1-R4 have following values:

which involves reaction of 2-methylfuran with available α,β-unsaturated carbonyl compounds in presence of copper (II) bromide in 1,2-dichloroethane at room temperature during 4 hours.

EFFECT: these compounds are of interest in synthesis of pharmaceutical substances.

1 cl, 2 tbl, 11ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method for methyl n-[3,4-dialkyl-5-(n-methoxy-n-oxoalkyl)-2-furyl]alkanoates production by the general formula where R = C2H5, C3H7, C4H9; R'=(CH2)nCOOCH3, n=5, 6, by reaction of dialkyl acetylenes of the general formula R-C≡C-R, where R=C2H5, C3H7, C4H9, with carboxylic acid esters in the presence of magnesium (Mg, powder) and Cp2TiCl2 catalyst with methyl esters α,ω-dicarboxylic acids CH3CO2(CH2)nCO2CH3, where n=5, 6, at the molar ratio of RC≡CR : CH3CO2(CH2)nCO2CH3:EtAlCl2 : Mg:Cp2TiCl2 = 10:20(50-70):40:(1.8-2.2) in tetrahydrofuran under argon atmosphere at 60°C and atmospheric pressure during 4-8. Methyl n-[3,4-dialkyl-5-(n-methoxy-n-oxoalkyl)-2-furyl]alkanoates (1) yield is 54-76%.

EFFECT: compound are important as initial synthons for biologically active compounds creation for medical and agricultural purposes, exhibiting antibacterial, antiviral, anti-inflammatory, antifungal, antitumor, analgesic, anticonvulsant properties.

1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: anhydrous cobalt acetylacetonate is mixed with an organic solvent and stirred until it is completely dissolved at room temperature. As the organic solvent, a lower ketone is used, then a furancarboxylic acid of general formula RCOOH is introduced into the resulting solution, where R = unsubstituted furyl, substituted furyl, in the ratio of cobalt acetylacetonate cobalt: furancarboxylic acid of 1:2, is kept for about 10 minutes before the precipitation of the cobalt salts of general formula (RCOO)2Co, where R = furyl, substituted furyl, the resulting mixture is stirred for 50 minutes until the cobalt salt is completely separated, filtered, the resulting precipitate is washed with a lower ketone and air dried.

EFFECT: expansion of raw materials base of reagents for obtaining cobalt salts, simplification of technology.

2 ex

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