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 PDFInfo
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Abstract
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)
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CS931160A CZ116093A3 (en) | 1992-10-14 | 1992-10-14 | Packet switch |
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SK116092A3 SK116092A3 (en) | 1995-08-09 |
SK277942B6 true SK277942B6 (en) | 1995-08-09 |
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Cited By (1)
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 |
Families Citing this family (1)
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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 |
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1992
- 1992-04-16 SK SK116092A patent/SK277942B6/en unknown
- 1992-10-14 CZ CS931160A patent/CZ116093A3/en unknown
Cited By (1)
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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CZ116093A3 (en) | 1993-12-15 |
SK116092A3 (en) | 1995-08-09 |
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