SK277942B6 - R-chromone-3-carbaldehyd-n-(aroyl) hydrazones and method of their preparation - Google Patents

R-chromone-3-carbaldehyd-n-(aroyl) hydrazones and method of their preparation Download PDF

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SK277942B6
SK277942B6 SK116092A SK116092A SK277942B6 SK 277942 B6 SK277942 B6 SK 277942B6 SK 116092 A SK116092 A SK 116092A SK 116092 A SK116092 A SK 116092A SK 277942 B6 SK277942 B6 SK 277942B6
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SK116092A3 (en
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Margita Lacova
Hafez M El-Shaaer
Zelmira Odlerova
Mikulas Furdik
Jarmila Chovancova
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Margita Lacova
El-Shaaer Hafez, M.
Zelmira Odlerova
Mikulas Furdik
Jarmila Chovancova
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Publication of SK277942B6 publication Critical patent/SK277942B6/en

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Abstract

R-Chromone-3-carbaldehyd -N-(aroyl) hydrazones with general formula I, where Ar is 4-C sub.5 H sub.4 N, C sub.6 H sub.5, 2-HO-C sub.6 H sub.4, 3,4,5-(HO) sub.3C sub.6 H sub.2; R is H, 6-OH, 7-OH, 7,8-(OH) sub.2, 6-Cl, 6-CH sub.3 and method of their preparation which is depended on condensation of R-3- -formylchromons with ArCONHNH sub.2 in alcohol medium or other internal solvent by acidic catalyst at 50 to 80 degrees of Celsius temperatures. Compounds are characterized by antimycobacterial effect.

Description

SK 277942 Β6 C H N 62,13 zistené % 3,55 13,57 C H N 62,24 3,73 13,65 2. 6-Metyl-3-chromónkarbaldehyd-N-(izonikoti-noyl)hydrazón, teplota topenia 207-209'C. Analýza pre C17H1JN3O3 (M = 307,3) vypočítané % C H N 66,44 zistené % 4,26 3,67 C H N 66,69 4,46 3,48 3. 6-Chlór-3-chromónkarbaldehyd-N-(Ízonikoti· noyl)hydrazón, teplota topenia 208-210°C. Analýza pre C16H10CIN3O3 (M = 327,7) vypočítané % C H N C1 59,26 3,08 12,81 10,81 zistené % C H N C1 59,38 3,16 12,94 10,87 4, 7-Hydroxy-3-chromónkarbaldehyd-N-(izomkoti· noyl)hydrazón, teplota topenia 239-240*C. Analýza pre C ι«Ηι iN304 (M = 309,3) vypočítané % C H N 62,13 zistené % 3,56 13,59 C H N 62,28 3,82 13,12 C H N 59,08 zistené % 3,39 12,92 C H N 58,72 3,40 12,68 C H N 62,96 zistené % 3,73 8,63 C H N 62,98 3,73 8,24 C H N 67,04 zistené % 4,34 8,69 C H N 67,28 4,41 8,58SK 277942 Β6 CHN 62.13 found% 3.55 13.57 CHN 62.24 3.73 13.65 2. 6-Methyl-3-chromonecarbaldehyde-N- (isonicotinyl) hydrazone, mp 207-209 ' C. Analysis for C 17 H 11 N 3 O 3 (M = 307.3) calculated% CHN 66.44 found% 4.26 3.67 CHN 66.69 4.46 3.48 3. 6-Chloro-3-chromoncarbaldehyde-N- (isonicotinyl) hydrazone, mp 208-210 ° C. Analysis for C 16 H 10 ClN 3 O 3 (M = 327.7) calculated% CHN Cl 59.26 3.08 12.81 10.81 Found% CHN C1 59.38 3.16 12.94 10.87 4, 7-Hydroxy-3- chromoncarbaldehyde-N- (isomotothiyl) hydrazone, mp 239-240 ° C. Analysis C ιHΗΗN304O ((M = 309.3) Calculated% CHN 62.13 Found% 3.56 13.59 CHN 62.28 3.82 13.12 CHN 59.08 Found% 3.39 12.92 CHN 58.72 3.40 12.68 CHN 62.96 Found% 3.73 8.63 CHN 62.98 3.73 8.24 CHN 67.04 Found% 4.34 8.69 CHN 67.28 4 41 8.58

Oblasť technikyTechnical field

Deriváty R-chromón-3-karbaldehyd-N-(aroyl )hydra-zónu a ich spôsob prípravy. Tieto zlúčeniny sa vyznačujú antimykobakteriálnou účinnosťou.R-chromone-3-carbaldehyde-N- (aroyl) hydrazone derivatives and their preparation. These compounds have antimycobacterial activity.

Doterajší stav technikyBackground Art

Doteraz je opísaných mnoho typov biologicky účinných látok z oblasti syntetických alebo prírodných derivátov chromónu napr. antialergické vlastnosti sú opisané autormi: Brown R. C., Harard M. J. US 4 238 606 (1980); Cairus H. s kol. Ger. Oflen 2 851 440; bakterí-cídne účinky sú opísané firmou Eisai Co. Jpn. Kokaj Tokyo Koho 80, 111 489; Róma G. a kol. Farmaco Ed. SCI. (1978), 33 822. Pri derivátoch 3-formylchromónu nebola doposiaľ zistená antituberkulózna aktivita.To date, many types of biologically active substances in the field of synthetic or natural chromone derivatives have been described, e.g. antiallergic properties are described by: Brown R.C., Harard M.J., US 4,238,606 (1980); Cairus H. et al. Ger. Oflen 2 851 440; bacterial effects are described by Eisai Co. et al. Jpn. Kokaj Tokyo Koho 80, 111,489; Roma G. et al. Farmaco Ed. SCI. (1978), 33,822. Antituberculous activity has not yet been found for 3-formylchromone derivatives.

Podstata vynálezuSUMMARY OF THE INVENTION

Podstatou vynálezu sú R-chromón-3-karbaldehyd-N--(aroyl) hydrazôny všeobecného vzorca IThe present invention provides R-chromone-3-carbaldehyde-N - (aroyl) hydrazones of the formula I

kde R je H, 6-OH, 7-OH, 7,8-(0¾,6-C1,6-CHj; Ar je 4-C5H4N, C5H5,2-HOCÄ, 3,4,5-(0¾¾. Súčasne bol nájdený spôsob prípravy zlúčenín všeobecného vzorca I, ktorého podstata podľa vynálezu spočíva v tom, že sa kondenzuje R-chromón-3-karbalde-hyd s aroylhydrazínmi (ArCONHNHj) v alkohole za kyslej katalýzy. Súčasne sa v testoch zistilo, že zlúčeniny podľa vynálezu majú antimykobakteríálne účinky proti Mycobac-terium tuberculosis HnRv, porovnateľné s hydrazidom kyseliny izonikotínovej. V koncentrácii 1 pg.ctn 3 napr. zlúčenín 1,2 z príkladu 2 sú mykonakterícídne ako INH.wherein R is H, 6-OH, 7-OH, 7,8- (0, 6-C 1-6 -CH 3; Ar is 4-C 5 H 4 N, C 5 H 5, 2-HOC 2, 3, 4, 5 (0, 5 '). a process for the preparation of compounds of formula (I) has been found which consists in condensing R-chromone-3-carbaldehyde with aroylhydrazines (ArCONHNH 3) in alcohol under acid catalysis. they have antimycobacterial activity against Mycobacterium tuberculosis HnRv, comparable to isonicotinic hydrazide.In a concentration of 1 µg / ml, for example, compounds 1.2 of Example 2 are mykonacterial as INH.

Príklady uskutočnenia vynálezu Príklad 1EXAMPLES Example 1

Príprava 6-hydroxy-3-chromónkarbaldehyd-N-( izoniko-tinoyljhydrazónu 6-Hydroxy-3-formylchromôn (10 nunol) sa rozpusti v etanole (40 cm*3), za miešania sa pridá suspenzia hyd-razidu kyseliny izonikotinovej (10 mmol) v etanole a kyselina p-toluénsulfúnová (cca 0,1 mmol). Reakčná zmes sa zahreje na reflux, v priebehu niekoľkých minút sa začne vylučovať hydrazón, reflux sa udržuje približne 10 minút, potom sa zrazenina z teplého etanolu odsaje. Ak sa zrazenina nevylúči po 30 minútovom refluxe, reakčná zmes sa zriedi vodou a vylúčená zrazenina sa odsaje a prečistí z vhodného rozpúšťadla, ktorým je etanol, dime-tylsulfoxid a pod. Ďalej sa uvedené zlúčeniny pripravili podľa uvedeného predpisu.Dissolve 6-hydroxy-3-chromonic carbaldehyde-N- (isonicotinoylhydrazone 6-Hydroxy-3-formylchromone (10 nunol) in ethanol (40 cm 3), add isonicotinic acid hydrazide suspension (10 mmol) with stirring ) in ethanol and p-toluenesulfonic acid (about 0.1 mmol) The reaction mixture is heated to reflux, hydrazone is precipitated within a few minutes, reflux is maintained for about 10 minutes, then the precipitate from warm ethanol is filtered off with suction. the mixture is diluted with water and the precipitate formed is filtered off with suction and purified from a suitable solvent, ethanol, dimethylsulfoxide, etc. The compounds are prepared according to the aforementioned formula.

Príklad 2 1. 6-Hydroxy-3-chromônkarbaldehyd-N-(izonikoti-noyljhydrazún, teplota topenia 250-252°C.Example 2 1. 6-Hydroxy-3-chromonecarbaldehyde-N- (isonicotinylhydrazine, mp 250-252 ° C.

Analýza pre CitHuN]C>4 (M = 309,3) vypočítané % 5. 7,8-Dihydroxy-3-chromónkarbaldehyd-N-(izoni-kotinoyljhydrazón, teplota topenia 254-2SS°C.Analysis for CitHNN4 C &4 (M = 309.3) calculated% 5. 7,8-Dihydroxy-3-chromonecarbaldehyde-N- (isonotino-dihydrazone, mp 254-2SS ° C.

Analýza pre CuHnNsOs (M = 325) vypočítané % 6. 6-Hydroxy-3-chromónkarbaldehyd-N<2-hydro-xybenoyljhydrazón, teplota topenia 240-241°C.Analysis for C 11 H 11 N 5 O 5 (M = 325) calculated% 6. 6-Hydroxy-3-chromonecarbaldehyde-N, 2-hydroxy-benzoylhydrazone, mp 240-241 ° C.

Analýza pre C17H1 jNjOs (M = 324,3) vypočítané % 7. 6-Metyl-3-chromónkarbaldehyd-N-(2-hydroxy-benoyljhydrazón, teplota topenia 220-22leC.Analysis for C 17 H 11 N 3 O 5 (M = 324.3) calculated% 7. 6-Methyl-3-chromoncarbaldehyde-N- (2-hydroxy-benoylhydrazone, mp 220-22leC.

Analýza pre C1SH14Ň2O4 (M = 322,3) vypočítané % 8. 7-Hydroxy-3-chromónkarbaldehyd-N-(2-hydro- 2Analysis for C 18 H 14 N 2 O 4 (M = 322.3) calculated% 8. 7-Hydroxy-3-chromoncarbaldehyde-N- (2-hydro-2

Claims (3)

SK 277942 B6 xybenoyl)hydra2Ôn, teplota topenia 262-263’C. Analýza pre C17H1 2N20j(M = 324,3) vypočítané % C H N 62,96 zistené % 3,73 8,63 C H N 62,63 3,71 8,51 9. 6-Hydroxy-3-chromónkarbaldehyd-N-{3,4,5-tri-hydroxybenzoyl)hydrazón, teplota topenia 267-270°C. Analýza pre C17H12N2O7 (M = 356,2) vypočítané % C H N 57,30 zistené % 3,39 7,86 C H N 57,59 3,48 8,14 10. 7,8-Dihydroxy-3-chromónkarbaldehyd-N-(314,5· -trihydroxybenzoyl)hydrazón, -270°C. teplota topenia 267' Analýza pre C17H12N2O8 (M = 372,2) vypočítané % C H N 54,80 zistené % 3,23 7,53 C H N 54,99 3,44 7,75 11. 6-Metyl-3-chromónkarbaldehyd-N-(3,4,5-trihyd-roxybenzoyl)hydrazón, teplota topenia 215-217°C. Analýza pre CigHi^Oe (M = 354,2) vypočítané % C H N 61,01 zistené % 3,98 7,91 C H N 61,09 4,23 7,74CZ-277942 B6 xybenoyl) hydra2n, mp 262-263’C. Analysis for C 17 H 12 N 2 O 3 (M = 324.3) calculated% CHN 62.96 found% 3.73 8.63 CHN 62.63 3.71 8.51 9. 6-Hydroxy-3-chromonecarbaldehyde-N- {3, 4,5-trihydroxybenzoyl) hydrazone, mp 267-270 ° C. Analysis for C 17 H 12 N 2 O 7 (M = 356.2) calculated% CHN 57.30 found% 3.39 7.86 CHN 57.59 3.48 8.14 10. 7,8-Dihydroxy-3-chromoncarbaldehyde-N- (314) 5, 5-trihydroxybenzoyl) hydrazone, -270 ° C. mp 267 ° C for C 17 H 12 N 2 O 8 (M = 372.2) calculated% CHN 54.80 found% 3.23 7.53 CHN 54.99 3.44 7.75 11. 6-Methyl-3-chromonecarbaldehyde-N- (3,4,5-trihydroxybenzoyl) hydrazone, mp 215-217 ° C. Analysis CigigH ^ OOe (M = 354.2) Calculated% C H N 61.01 Found% 3.98 7.91 C H N 61.09 4.23 7.74 kde R je H, 6-OH, 7-OH, 7,8-(OH)i, 6-C1, 6-CH3, Ar je 4-C5H4N, CsHj, 2-HOC«K», 3,4,5-(OH)3C6H2.wherein R is H, 6-OH, 7-OH, 7,8- (OH) 1,6-C1-6-CH3, Ar is 4-C5H4N, CsH3, 2-HOCK3, 3,4,5 - (OH) 3C6H2. 2. Spôsob prípravy zlúčenín všeobecného vzorca I podľa nároku 1, vyznačujúci sa tým, že sa kondenzuje R-3-formylchromón s aroylhydrazí-nom A1CONHNH2, kde R a Ar majú výaiam uvedený v nároku 1, v alkohole alebo v inom inertnom rozpúšťadle, pri teplote 50 až 80°C, výhodne za kyslej katalý-zy, napr. p-toluénsulfónovou kyselinou. Koniec dokumentu 12.Process for the preparation of compounds of the formula I according to claim 1, characterized in that R-3-formylchromone is coupled with aroylhydrazine A1CONHNH2, wherein R and Ar are as defined in claim 1, in an alcohol or in another inert solvent, a temperature of 50 to 80 ° C, preferably an acid catalysis, e.g. p-toluenesulfonic acid. End of Document 12. 3-Chromónkarbaldehyd-N-(2-hydroxybenzo-yl)hydrazión, teplota telenia 222-224°C. Analýza pre C17H11N2O4 (M = 308,3) vypočítané % C H N 66,28 zistené % 3,92 9,08 C H N 66,35 3,95 8,96 Priemyselné využiteľnosť Zlúčeniny podľa vynálezu sa môžu používať v práškovej alebo tabletovej forme, respektíve v roztokoch a-lebo so zmáčadlami samotné alebo v zmesiach s inými antituberkulóznymi, respektíve s baktericidnymi, fungi-cídnymi prostriedkami na dezinfekciu alebo na iné pro-timikróbne účely. PATENTOVÉ NÁROKY 1. R-Chromón-3-karbaldehyd-N-(aroyl)hydrazóny všeobecného vzorca I 33-Chromocarbaldehyde-N- (2-hydroxybenzoyl) hydrazione, mp 222-224 ° C. Analysis for C 17 H 11 N 2 O 4 (M = 308.3) calculated% CHN 66.28 found% 3.92 9.08 CHN 66.35 3.95 8.96 Industrial Applicability The compounds of the invention may be used in powder or tablet form, respectively solutions or wetting agents alone or in mixtures with other antituberculous or bactericidal, fungicidal, disinfectant or other pro-microbial purposes. 1. R-Chromon-3-carbaldehyde-N- (aroyl) hydrazones of Formula I 3
SK116092A 1992-10-14 1992-04-16 R-chromone-3-carbaldehyd-n-(aroyl) hydrazones and method of their preparation SK277942B6 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2764290A1 (en) * 1997-06-04 1998-12-11 Nihon Bayer Agrochem Kk HYDRAZIDE DERIVATIVES OF ISONICOTINIC ACID

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* Cited by examiner, † Cited by third party
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US10266510B2 (en) 2017-01-18 2019-04-23 King Abdulaziz University Antimicrobial and cytotoxic compounds and methods for treating cancer, a bacterial infection, and/or a fungal infection

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2764290A1 (en) * 1997-06-04 1998-12-11 Nihon Bayer Agrochem Kk HYDRAZIDE DERIVATIVES OF ISONICOTINIC ACID

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