CS275632B6 - 6-C3 Nnamylideneamino-2-ethylthienzothiazole - Google Patents

6-C3 Nnamylideneamino-2-ethylthienzothiazole Download PDF

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CS275632B6
CS275632B6 CS556089A CS556089A CS275632B6 CS 275632 B6 CS275632 B6 CS 275632B6 CS 556089 A CS556089 A CS 556089A CS 556089 A CS556089 A CS 556089A CS 275632 B6 CS275632 B6 CS 275632B6
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agar
substance
growth
compound
ethylthiobenzothiazole
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CS556089A
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Czech (cs)
Slovak (sk)
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CS8905560A1 (en
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Eva Ing Csc Sidoova
Veronika Doc Mvdr C Ciganekova
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Univ Komenskeho
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Abstract

Bol připravený doteraz neznámy 6-cinnamyli- · |L.) dénamino-2-etyltiobenzotiazol. Syntéza uvedenej zlúčeniny sa uskutočňuje reakciou 6-amino-2-etyltiobenzotiazolu a cinnamaldehydu skořicového v etanole za varu. Zlúčenina je antibakteriálne účinná proti anaerobně sporulujúcim baktériám rodu Clostridi um.The previously unknown 6-cinnamyl- |L.) denamino-2-ethylthiobenzothiazole was prepared. The synthesis of the above compound is carried out by the reaction of 6-amino-2-ethylthiobenzothiazole and cinnamaldehyde in ethanol under boiling conditions. The compound is antibacterially effective against anaerobically sporulating bacteria of the genus Clostridium.

Description

Predmetom vynálezu je 6-cinnamylidénamino-2-etyltiobenzotiazol.The present invention provides 6-cinnamylideneamino-2-ethylthiobenzothiazole.

ó-Meleini.mido-2-n-propyltiobenzotiazol prejavil účinnost’ proti anaerobně sporulujúcim baktéri.ám rodu Clostridium (Sidóová, E., Zemanová, M., Cigáneková, V. a Kallová, J., čs. autorské osvedčenie č. 270146).6-Melamine-2-n-propylthiobenzothiazole has shown activity against anaerobically sporulating bacteria of the genus Clostridium (Sidóová, E., Zemanová, M., Cigáneková, V. and Kallová, J., Czechoslovak Author's Certificate No. 270146 ).

Teraz sme zistili, že doteraz neznáma zlúčenina vzorcaWe have now found that a hitherto unknown compound of the formula

je antibakteriálne účinná proti anaerobně sporulujúcim baktériám rodu Clostridium.is antibacterially active against anaerobically sporulating bacteria of the genus Clostridium.

Súčasne bol zistený spósob přípravy uvedenj zlúčeniny reakciou 6-ami.no-2-etyltiobenzotiazolu a cinnamaldehydu v etanole za varu.At the same time, a method for preparing the title compound by reacting 6-amino-2-ethylthiobenzothiazole and cinnamaldehyde in boiling ethanol was discovered.

Nasledúce příklady bližšie osvetlujú, ale nijako neobmedzujú přípravu a vlastnosti zlúčeniny podl’a vynálezu.The following examples illustrate, but do not limit, the preparation and properties of the compound of the invention.

Příklad 1Example 1

Příprava 6-cínnamylidénamino-2-etyltiobenzotiazoluPreparation of 6-cinnamylideneamino-2-ethylthiobenzothiazole

6-Amino-2-etyltiobenzotiazol (21,0 g, 0,1 mól) a cinnamaldehyd (13,2 g, 0,1 mól) sa rozpustili v etanole (60 cm^) a reakčná zmes sa zahriala do varu na 5 mlnút. Potom sa k roztoku přidala studená voda do prvého slabého zákalu, zmes sa odfarbila aktívnym uhlím za varu a roztok sa přefiltroval cez vyhrievaný lievik. Z filtrátu po ochladení na 5 °C sa získal 6-ci.nnamyládénamino-2-etyltiobenzotiazol s t.t. 93 až 95 °C v množstve 26,2 g (80,7 %). Látka nevyžadovala dalšie čistenie. M.h. = 324,47.6-Amino-2-ethylthiobenzothiazole (21.0 g, 0.1 mol) and cinnamaldehyde (13.2 g, 0.1 mol) were dissolved in ethanol (60 cm 3) and the reaction mixture was heated to reflux for 5 ml. . Then, cold water was added to the solution until the first slight turbidity, the mixture was decolorized with boiling activated carbon, and the solution was filtered through a heated funnel. From the filtrate, after cooling to 5 ° C, 6-cyanamethyladeneamino-2-ethylthiobenzothiazole with m.p. 93-95 ° C in an amount of 26.2 g (80.7%). The fabric did not require further purification. M.h. = 324.47.

Pře C18H16N2S2 vypočítané % : C 66,63 H 4,97 N 8,63 S 19,76 zistené : 66,80 5,06 8,53 19,98For C 18 H 16 N 2 S 2 calculated%: C 66.63 H 4.97 N 8.63 S 19.76 found: 66.80 5.06 8.53 19.98

Příklad 2Example 2

Antibakteriálna aktivita zlúčeniny podía vynálezu proti vybraným zástupcom anaerobně sporulujúcich baktérií rodu Clostridium (10~^ mól dm ^) v proovnaní s účinnosťou 2-merkaprobenzotiazolu (2-MBT)The antibacterial activity of the compound according to the invention against selected representatives of anaerobically sporulating bacteria of the genus Clostridium (10 .mu.mol dm @ 2) in comparison with the activity of 2-mercaprobenzothiazole (2-MBT)

Látka Fabric MIC (10-z MIC (10 -z mól dnT^) ' mól dnT ^) ' Clostridium perfringens typ A (CCM 5703) Clostridium perfringens type A (CCM 5703) Clostridium perfringens typ C (CCM 5705) Clostridium perfringens type C (CCM 5705) Clostridium sporogenes (Cl 15/49 SZU) Clostridium sporogenes (Cl 15/49 SZU) Clostridi um bifermentans (Cl 1/46 SZU) Clostridi um bifermentans (Cl 1/46 SZU) Zlúčenina podía vynálezu A compound of the invention 500 500 500 500 500 500 500 500 2-MBT 2-MBT > 1 000 > 1,000 > 1 000 > 1,000 > 1 000 > 1,000 > 1 000 > 1,000

MIC = minimálna inhibičná koncentrácia (najnižšia koncentrácia zo skúšaných koncentrácii látok, ktorá plné inhibuje rast a rozmnožovanie testovaných druhov klostrídií).MIC = minimum inhibitory concentration (the lowest concentration of the test substance that fully inhibits the growth and reproduction of the Clostridial species tested).

> = uvedená koncentrácia neinhibuje rast klostrídií.> = the indicated concentration does not inhibit the growth of clostridia.

CS 275632 Β 6CS 275632 Β 6

Účinok študovanej látky na rast a rozmnožovanie anaerobně sporulujúcich baktérií rodu Clostridium sa zisťoval agarovou dilučnou metodou na tuhých živných půdách s různou koncentráciou pridanej študovanej látky. Látka bola rozpuštěná v dimetylsulfoxide. Koncentrácia rozpúšťadla v kultivačnej půdě nepřekročila 1 Použité kultivačně půdy : VI agar a Muller-Hintonov agar (komerčně výrobky Imuny, n.p. Šarišské Michalany), VI agar a MUllerHintonov agar obohatený □ 5 % defibrinovanej konskej krvi. Analogicky bolí naočkované kontrolně půdy bez pridania študovanej látky. Inhibícia rastu kmeňov klostrídií bola hodnotená po 30 a 50 hodinovej inkubácii naočkovaných živných médií v anaeróbnom termostate při 37 °C, kedy kontroly (půdy naočkované testovanými kmeňmi klostrídií bez pridania študovanej látky) dosiahli maximálny rast.The effect of the study substance on the growth and multiplication of anaerobically sporulating bacteria of the genus Clostridium was determined by the agar dilution method on solid nutrient media with different concentrations of added study substance. The substance was dissolved in dimethyl sulfoxide. The solvent concentration in the culture medium did not exceed 1 Culture media used: VI agar and Muller-Hinton agar (commercial products Imuny, n.p. Šarišské Michalany), VI agar and MUllerHinton agar enriched with □ 5% defibrinated horse blood. Analogously, inoculated control soils were in pain without the addition of the study substance. Growth inhibition of Clostridial strains was assessed after 30 and 50 hours of incubation of inoculated nutrient media in an anaerobic thermostat at 37 ° C, when controls (soils inoculated with test Clostridial strains without addition of study substance) reached maximal growth.

Významný je fakt, že zlúčenina podlá vynálezu je novej doteraz neznámej štruktúry a plné inhibuje rast a rozmnožovanie testovaných anaerobně sporulujúcich baktérií rodu Clostridium v koncentrácii 500.10-6 mol dm-3.Significantly, the compound of the invention is of a new hitherto unknown structure and fully inhibits the growth and multiplication of the tested anaerobically sporulating bacteria of the genus Clostridium at a concentration of 500.10 -6 mol dm -3 .

Zlúčeninu podlá vynálezu možno používat’ ako účinnú zložku antibakteriálnych prípravkov samostatné, alebo v zmesi s inými látkami, óalej ako medziprodukt pře ďalšie syntézy.The compound according to the invention can be used as an active ingredient of antibacterial preparations alone or in a mixture with other substances, as well as as an intermediate for further syntheses.

Claims (2)

Λ CS 275632 Β 6 2 Účinok študovanéj látky na rast a rozmnožovanie anaerobně sporulujúcich baktérií roduClostridium sa zisťoval agarovou dilučnou metodou na tuhých živných půdách s různou kon-centráciou pridanej študovanej látky. Látka bola rozpuštěná v dimetylsulfoxide. Koncentrá-cia rozpúšťadla v kultivačnej půdě nepřekročila 1 %. Použité kultivačně půdy : VI agar aMuller-Hintonov agar (komerčně výrobky Imuny, n.p. Šarišské Michalany), VI agar a Mílller-Hintonov agar obohatený o 5 % defibrinovanej konskej krvi. Analogicky bolí naočkovanékontrolně půdy bez pridania študovanej látky. Inhibícia rastu kmeňov klostrídií bola hodno-tená po 30 a 50 hodinovej inkubácii naočkovaných živných médií v anaeróbnom termostate při37 °C, kedy kontroly (půdy naočkované testovanými kmeňmi klostrídií bez pridania študova-nej látky) dosiahli maximálny rast. Významný je fakt, že zlúčenina podl’a vynálezu je novej doteraz neznámej strukturya plné inhibuje rast a rozmnožovanie testovaných anaerobně sporulujúcich baktérií roduClostridium v koncentrácii 500.10-6 mol dm-3. Zlúčeninu podl’a vynálezu možno používat’ ako účinnú zložku antibakteriálnych prípravkovsamostatné, alebo v zmesi s inými látkami, áalej ako medziprodukt pře ďalšie syntézy. PATENTOVÉ NÁROKY 1. 6-Cinnamylidénamino-2-etyltiobenzotiazol vzorca27 CS 275632 Β 6 2 The effect of the study substance on the growth and multiplication of anaerobic sporulating bacteria of the genus Clostridium was determined by the agar dilution method on solid nutrient media with varying concentrations of added study substance. The substance was dissolved in dimethyl sulfoxide. The solvent concentration in the culture medium did not exceed 1%. Cultures used: VI agar and Muller-Hinton agar (commercially manufactured by Imuny, n. Saris Michalany), VI agar and Milller-Hinton agar enriched with 5% defibrinated horse blood. Analogously, the soil is inoculated without control substance addition. Growth inhibition of clostridial strains was evaluated after 30 and 50 hours incubation of inoculated nutrient media in anaerobic thermostate at 37 ° C, when controls (soils inoculated with test strains of clostridia without addition of study substance) reached maximum growth. Significantly, the compound of the present invention is a novel hitherto unknown structure and fully inhibits the growth and multiplication of test anaerobic sporulating bacteria of the genus Clostridium at a concentration of 500.10-6 mol dm-3. The compound of the invention can be used as an active ingredient of antibacterial preparations, alone or in admixture with other substances, as an intermediate for further syntheses. CLAIMS 1. 6-Cinnamylideneamino-2-ethylthiobenzothiazole Formula ,-CH=CH-CH=N-r>x, -CH = CH-CH = N-r x CH2-CH3CH 2 -CH 3 2. Spůsob přípravy zlúčeniny podlá bodu 1, vyznačený tým, že sa nechá reagovat 6-amino--2-etyltiobenzotiazol s cinnamaldehydom v etanole za varu.2. Process for the preparation of a compound according to claim 1, characterized in that 6-amino-2-ethylthiobenzothiazole is reacted with cinnamaldehyde in ethanol at boiling point.
CS556089A 1989-09-29 1989-09-29 6-C3 Nnamylideneamino-2-ethylthienzothiazole CS275632B6 (en)

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