CS276501B6 - 6-Cinnamylideneamino-2-benzothiazolinothion · - Google Patents

6-Cinnamylideneamino-2-benzothiazolinothion · Download PDF

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CS276501B6
CS276501B6 CS555889A CS555889A CS276501B6 CS 276501 B6 CS276501 B6 CS 276501B6 CS 555889 A CS555889 A CS 555889A CS 555889 A CS555889 A CS 555889A CS 276501 B6 CS276501 B6 CS 276501B6
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CS
Czechoslovakia
Prior art keywords
compound
inoculated
benzothiazolinothione
growth
anaerobic
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CS555889A
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Czech (cs)
Slovak (sk)
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CS8905558A1 (en
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Eva Ing Csc Sidoova
Veronika Doc Mvdr C Ciganekova
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Uk Prirodovedecke Fakulta
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Priority to CS555889A priority Critical patent/CS276501B6/en
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Publication of CS276501B6 publication Critical patent/CS276501B6/en

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Abstract

Bol připravený doteraz neznámy 6-cinnamylidénamino-2-benzotiazolíntión. Syntéza uvedenej zlúčeniny sa uskutočňuje reakciou 6-amino-2-benzotiazolíntiónu s cinnamaldehydom v zmesi dimetylsulfoxidu a etanolu za varu. Zlúčeniny je antibakteriólne účinná proti anaerobně sporulujúcim baktériám rodu Clostridium.The previously unknown 6-cinnamylideneamino-2-benzothiazolinethione was prepared. The synthesis of the above compound is carried out by the reaction of 6-amino-2-benzothiazolinethione with cinnamaldehyde in a mixture of dimethyl sulfoxide and ethanol at boiling temperature. The compound is antibacterially effective against anaerobic sporulating bacteria of the genus Clostridium.

Description

1 CS 276 501 B6

Predmetom vynálezu je 6-oinuamylidé"',amino-2-'sensotiazolíntióa. 6-Maleinimido-2-n-propyltiobenzotiazol, ktorý bol připravený zo 6-amino-2-benzotia-zolíntiónu, prejavil účinnost proti anaerobně sporulujúcim baktériám rodu Clostridium(Sidóová E., Zemanová M., Cigáneková V. a Kallová J,, (CS autorské osvedčenie č. 270 146).

Teraz sme zistili, že iný derivát odvodený tak isto od 6-amino-2-benzotiazolíntiónu,doteraz neznáma zlúčenina vzorca

je antibakteriálne účinná proti anaerobně sporulujúcim baktériám rodu Clostridium. · Súčasne bol zistený sposob přípravy uvedenej zlúčeniny reakciou 6-amino-2-benzotia-zolíntiónu (iným názvom 6-amino-2-merkaptobenzotiazolu) a cinnamaldehydu v zmesi dimetyl-sulfoxidu a etanolu za varu,

Nasledujúce příklady bližšie osvětlujú, ale nijako neobmedzujú přípravu a vlastnostizlúčeniny podlá vynálezuPříklad 1 Příprava 6-cinnamyliděnamino-2-benzotiazolíntiónu 6-amino-2-benzotiazolíntión (3,65 g, 0,02 mol) sa rozpustil v dimetylsulfoxide (20 cm3).K roztoku sa přidal cinnamaldehyd (2,65 g, 0,02 mol) a etanol (50 cm3). Zmes sa zahriala dovaru a po 5 minútaoh varu sa odfarbila sktívnym uhlím. Z filtrátu po ochladení na 5 °C saizoloval 6~cinna®ylidéaamiaO”2~b@nzotia2íslíntiéa a t. 139 až 191 °G v sanožstve 3,65 g(61,6 %). Látka nevyžadovala žialšie čistenie. M. h. = 296,41

Pre C16Hi2N2S2 vypočítané %: C 64,83 H 4,08 N'9,45 S 21,63 zistené% : 64,94 4,14 9,26 21,65 Příklad 2

Antibakteriálna aktivita zlúčeniny podlá vynálezu proti vybraným zástupcom anaerobně sporu-lujúcich baktérií rodu Clostridium (10 mol dm“J) v porovnaní s účinnostou.2-merkapto-benzotiazolu (2-MBT) Látka MIC (10"*6 mol dm"3) Clostridiumperfringenstyp A(CCM 5702) Clostridiumperfringenstyp C(CCM 5705) Clostridiumsporogenes(Cl 15/49 SZU) Clostridium bifermentans Cl 1/46 SZU) Zlúčenina podlávynálezu 1000 1000 1000 1000 2-MBT >1000 >1000 > 1000 >1000 MIC = minimálna inhibičná koncentrácia (najnižšia koncentrácia zo skúšaných koncentráciílátok, ktorá plné inhibuje rast a rozmnožovanie testovaných druhov klostrídií). > = uvedená koncentrácia neáňhibuje rast klostrídií. Účinok študovanej látky na rast a rozmnožovanie anaerobně sporulujúcich baktérií roduClostridium sa zisíoval agarovou dilučnou metodou na tuhých živných pSdach s rožnou kon-centráciou pridanej študovanej látky. Látka bola rozpuštěná v dimetylsulfoxide. Koncentrá-cia rozpúštadla v kultivačnej páde nepřekročila 1 %. Použité kultivačné pody: VL agar

1 CS 276 501 B6

The present invention relates to 6-ominoamylides, amino-2-sulfensothiazole. 6-Maleimimido-2-n-propylthiobenzothiazole, prepared from 6-amino-2-benzothiazolinothione, has shown activity against anaerobic sporulating bacteria of the genus Clostridium (Sido E., Zemanová M., Cigáneková V. and Kallová J ,, (CS Author's Certificate No. 270 146).

We have now found that another derivative derived from 6-amino-2-benzothiazolinothione, an unknown compound of formula

is antibacterially effective against anaerobic sporulating bacteria of the genus Clostridium. Simultaneously, a method of preparing said compound was found by reacting 6-amino-2-benzothiazolinothione (otherwise named 6-amino-2-mercaptobenzothiazole) and cinnamaldehyde in a mixture of dimethyl sulfoxide and ethanol at boiling,

EXAMPLES Example 1 Preparation of 6-cinnamylideneamino-2-benzothiazolinothione 6-amino-2-benzothiazolinothione (3.65 g, 0.02 mol) was dissolved in dimethylsulfoxide (20 cm 3). cinnamaldehyde (2.65 g, 0.02 mol) and ethanol (50 cm 3) were added. The mixture was warmed up and after 5 minutes boiling was decolorized with charcoal. From the filtrate, after cooling to 5 [deg.] C., 6-cinnamicylideaamia-2 < 2 > The fabric did not require any major cleaning. M. h. = 296.41

For C16H12N2S2 calculated%: C 64.83 H 4.08 N'9.45 S 21.63 found%: 64.94 4.14 9.26 21.65 Example 2

Antibacterial activity of the compound of the invention against selected representatives of anaerobic-defining bacteria of the genus Clostridium (10 mol dm J) compared to the activity of 2-mercapto-benzothiazole (2-MBT) MIC (10 "* 6 mol dm" 3) Clostridiumperfringenstyp A (CCM 5702) Clostridiumperfringenstyp C (CCM 5705) Clostridiumsporogenes (Cl 15/49 SZU) Clostridium bifermentans Cl 1/46 SZU) the lowest concentration from the concentrations tested, which fully inhibits the growth and multiplication of the tested species of clostridia). > = said concentration does not inhibit clostridial growth. 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 broths with a concentration of added study substance. The substance was dissolved in dimethyl sulfoxide. The concentration of solvent in the culture drop did not exceed 1%. Culture media used: VL agar

Claims (2)

CS 276 501 B6 a Můller-Hintonov agar (komerčně výrobky Imuny, n. p., Šarišské Michaiany), VL· agar a Mtil-ler-Hintonov agar obohatený o 5 % defibrinované j koňskéj krvi. Analogicky boli naočkovanékontrolně pody bez pridania študovanej látky. Inhibícia rastu kmeňov klostrídií bola hod-notená po 30 a 50 hodinovéj inkubácii naočkovaných živných médií v anaeróbnom termostatepri 37 °C, kedy kontroly (p3dy naočkované testovanými kmeňmi klostrídií bez pridania štu-dovanej látky) dosiahli maximálny rast. Významný je fakt, že zlúčenina pódia vynálezu je novej, doteraz nezhámej štruktúrya plné inhibuje rast a rozmnožovanie testovaných anaerobně sporulujúcich baktérií roduClostridium v koncentrácii 1000.10“θ mol dm“·^. Zlúčeninu pódia vynálezu možno používat ako účinnú zložku antibakteriálnych príprav-kov samostatné, alebo v zmesi s inými látkami, Stale j ako medziprodukt pře clalšie syntézy. PATENTOVÉ N A E OKY1. 6-Cinnamylidénamino-2-benzotiazolíntión vzorcaCS 276 501 B6 and Muller-Hinton agar (commercially manufactured by Imuny, N. p., Sarisske Michaiany), VL · agar and Mtiler-Hinton agar enriched with 5% defibrinated horse blood. Analogously they were inoculated with podes without addition of study substance. Growth inhibition of clostridial strains was evaluated after 30 and 50 hours incubation of the inoculated nutrient media in an anaerobic thermostate at 37 ° C, when the controls (inoculated with the test strains of clostridia without the addition of the drug) reached maximum growth. Significantly, the compound of the invention is a new, hitherto uninhibited structure and fully inhibits the growth and multiplication of test anaerobic sporulating bacteria of the genus Clostridium at a concentration of 1000.10 "θ mol dm" ·. The compound of the invention may be used as an active ingredient of antibacterial preparations alone or in admixture with other agents, still as an intermediate for more convenient synthesis. PATENT N AND E O1. 6-Cinnamylideneamino-2-benzothiazolinothione of the formula 2. SpSsob přípravy zlúčeniny pódia bodu 1, vyznačujúci sa tým, že sa nechá reagovat6-amino-2-benzotiazolíntión s cinnamaldehydom v zmesi dimetylsulfoxidu a etanolu za varu.2. A process for the preparation of a compound according to claim 1, characterized in that 6-amino-2-benzothiazolinothione is reacted with cinnamaldehyde in a mixture of dimethyl sulfoxide and ethanol at reflux.
CS555889A 1989-09-29 1989-09-29 6-Cinnamylideneamino-2-benzothiazolinothion · CS276501B6 (en)

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