CS275631B6 - 6-Amino-2- (3-pentylthio) benzothiazole - Google Patents
6-Amino-2- (3-pentylthio) benzothiazole Download PDFInfo
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- CS275631B6 CS275631B6 CS555989A CS555989A CS275631B6 CS 275631 B6 CS275631 B6 CS 275631B6 CS 555989 A CS555989 A CS 555989A CS 555989 A CS555989 A CS 555989A CS 275631 B6 CS275631 B6 CS 275631B6
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Abstract
Bol připravený doteraz neznámy 6-amino-2-/3-pentyltio/benzotiazol. Syntéza uvedenej zlúčeniny sa uskutočňuje reakciou draselnej soli 6-amino-2-merkaptobenzotiazolu s 3-pentylbromidom v prostředí dimetylformamid-voda. Zlúčenina je antibakteriálne účinná proti anaerobně sporulujúcim baktériám rodu Clostridium a proti kvašinkovo účinná proti Saccbaromyces cerevisiae.A previously unknown 6-amino-2-/3-pentylthio/benzothiazole has been prepared. The synthesis of the above compound is carried out by the reaction of the potassium salt of 6-amino-2-mercaptobenzothiazole with 3-pentyl bromide in a dimethylformamide-water medium. The compound is antibacterially active against anaerobic sporulating bacteria of the genus Clostridium and anti-yeastly active against Saccharomyces cerevisiae.
Description
Predmetom vynálezu je 6-amino-2-/3-pentyltio/benzotiazol. 6-Amino-2-n-pentyltiobenzotiazol prejavil dobru účinnost’ proti patogénnym kvasinkoví tým mikroorganizmom z rodu Candida, najma proti ich myceliárnej forme (Sidóová, E., Kuchta, T., Zemanová, M. a Straková,The present invention provides 6-amino-2- (3-pentylthio) benzothiazole. 6-Amino-2-n-pentylthiobenzothiazole has shown good activity against pathogenic yeasts by microorganisms of the genus Candida, in particular against their mycelial form (Sidóová, E., Kuchta, T., Zemanová, M. and Straková,
H., čs. autorské osvedčenie č. 261699).H., MS. author's certificate no. 261699).
Teraz sme zistilj, že doteraz neznáma zlúčenina vzorcaWe have now found that a hitherto unknown compound of the formula
S\ S \
C-S-CH 4 J ✓ je anti bakteriálně úči nná proti anaerobně sporulujúcim baktériám rodu Clostridium a zároveň je proti kvašinkovo účinná proti Saccharomyces cerevisiae.CS-CH 4 J ✓ is anti-bacterially active against anaerobically sporulating bacteria of the genus Clostridium and is also anti-yeast-active against Saccharomyces cerevisiae.
Súčasne bol zistený sposob přípravy uvedenj zlúčeniny na báze 6-amino-2-benzotiazolíntiónu (iným názvom 6-amino-2-merkaptobenzotiazolu) tým sposobom, že draselná sol 6-amino-2-merkaptobenzotiazolu sa alkyluje 3-pentylbromidom v prostředí zmesi dimetylformamidu s vodou, alebo dimetylsulfoxidu s vodou^At the same time, a method for preparing said compound based on 6-amino-2-benzothiazolinethione (also called 6-amino-2-mercaptobenzothiazole) was found by alkylating the potassium salt of 6-amino-2-mercaptobenzothiazole with 3-pentyl bromide in a mixture of dimethylformamide with dimethylformamide. water, or dimethyl sulfoxide with water ^
Nasledujúce příklady bližšie osvetlujú, ale nijako neobmedzujú přípravu a vlastnosti zlúčeniny podfa vynálezu.The following examples illustrate, but do not limit, the preparation and properties of the compound of the invention.
Příklad 1Example 1
Příprava 6-amino-2-/3-pentyltio/benzotiazoluPreparation of 6-amino-2- (3-pentylthio) benzothiazole
6-Amino-2-benzotiazolintión (9,1 g, 0,05 mól) sa rozpustil v roztoku hydroxidu draselného (3,3 g, 0,05 mól) vo vodě (17 cm5). K reakčnej zmesi sa za intenzívneho miešania přidal dimetylformamid (40 cm5) a len čo vznikol homogénny roztok, prilial sa k reakčnej zmesi v jednej dávke 3-pentylbromid (7,55 g, 0,05 mól). Reakčná zmes sa zahriala do varu a po 2 minutách varu sa bez zahrievania miešala 1 hodinu. Zmes sa potom vyliala na rozdrobený l’ad (600 g) a odstavila sa. Získal sa tuhý produkt s t.t. 61 až 63,5 °C v množstve 11,95 g (výťažok 94,7 %).6-Amino-2-benzothiazolinedione (9.1 g, 0.05 mol) was dissolved in a solution of potassium hydroxide (3.3 g, 0.05 mol) in water (17 cm 5 ). Dimethylformamide (40 cm 5 ) was added to the reaction mixture with vigorous stirring, and as soon as a homogeneous solution was formed, 3-pentyl bromide (7.55 g, 0.05 mol) was added to the reaction mixture in one portion. The reaction mixture was heated to reflux and, after boiling for 2 minutes, stirred for 1 hour without heating. The mixture was then poured onto crushed ice (600 g) and set aside. The solid product was obtained with a mp of 61-63.5 ° C in an amount of 11.95 g (yield 94.7%).
Vzorka pre analýzu bola prekryštalizovaná zo zmesi etanol - voda v pomere 3:1 za použltia áktívneho uhlia, z roztoku po ochladení na -16 °C sa získal čistý 6-amino-2-/3-[ientyltio/benzotiazol s t.t. 63 až 64 °C.A sample for analysis was recrystallized from ethanol: water 3: 1 using activated charcoal, and pure 6-amino-2- [3- [gentylthio] benzothiazole was obtained from the solution after cooling to -16 ° C, m.p. 63-64 ° C.
Pre C.QH.,N9S„ (252,40)For C. Q H., N 9 S „(252.40)
X Z 1 o Z Z vypočítané °-i : C 57,10 H 6,39 M 11,10 S 25,41 zi.stené % : 57,00 6,40 11,31 25,12X Z 1 o Z Z calculated ° -i: C 57.10 H 6.39 M 11.10 S 25.41 wall%: 57.00 6.40 11.31 25.12
Příklad 2Example 2
Antibakteriálna aktivita zlúčeniny podl’a vynálezu proti vybraným zástupcom anaerobně sporulujúcich bakterií rodu Clostridium (10-6 mól dm-5) v porovnaní s účinnosťou 2-merkaptobenzoti.azolu (2-MBT)Antibacterial activity of a compound of the invention against selected representatives of anaerobically sporulating bacteria of the genus Clostridium (10 -6 mol dm -5 ) compared to the activity of 2-mercaptobenzothiazole (2-MBT)
CS 275631 B 6CS 275631 B 6
MIC = niJnimúlna inhibičná koncentrácia (najnižšia koncentrácia zo skúšaných koncentracií látok, ktorá plné inhibuje rast a rozmnožovánie testovaných druhov klostrídií).MIC = minimum inhibitory concentration (the lowest concentration of the test concentrations of a 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.
Účinok študovanej látky na rast a rozmnožovánie anaerobně sporulujúcich baktérií rodu Clostridium sa zisťoval agarovou dilučnou metodou na tuhých živných půdách s různou koncentráciou pridanej študovanej látky. Látka béla rozpuštěná v dimetylsulfoxide. Koncentrácia rozpúšťadla v kultivačnej půdě nepřekročila 1 %. Použité kultivačně půdy : VI agar a Muller-Hintonov agar obohatený o 5 % def ibrinovanej konskej krvi. Analogicky bolí naočkované kontrolně půdy bez pridania študovanej látky. Inhibícia rastu kmeňov klostrídií bola hodnotená po 30 až 50 hodinovej inkubácii naočkovaných živných médií v anaeróbnom termostate pri 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 the 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 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 30-50 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.
Příklad 3Example 3
Proti kvašinková účinnost’ zlúčeniny podlá vynálezu proti Saccharomyces cerevisiae (10-6 mól dm 3) v porovnaní s účinnosťou 2-merkaptobenzotiazolu (2-MBT) :Anti-yeast activity of the compound according to the invention against Saccharomyces cerevisiae (10 -6 mol dm 3 ) in comparison with the activity of 2-mercaptobenzothiazole (2-MBT):
LátkaFabric
MIC (10-6 mól dm-3) v 3. deň kultivácieMIC (10 -6 mol dm -3 ) on the 3rd day of cultivation
Zlúčenina podlá vynálezuA compound of the invention
62,562.5
2-MBT2-MBT
000000
MIC = koncentrácia látky, plné inhibujúca rozmnožovánie kvasinky.MIC = concentration of the substance that fully inhibits yeast reproduction.
Pře stanovenie účinnosti proti Saccharomyces cerevisiae sa použila tekutá půda (5 cm3 v skúmavkách), kultivácia statická pri 28 °C. Látky rozpuštěné v dimetylsulfoxide sa dávkovali do půdy, potom inokulum. Rozmnožovanie kvasiniek sa sledovalo turbidimetricky. Liquid medium (5 cm 3 in tubes), static culture at 28 ° C, was used to determine activity against Saccharomyces cerevisiae. Substances dissolved in dimethyl sulfoxide were metered into the soil, then the inoculum. Yeast reproduction was monitored turbidimetrically.
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 mól dm-3. Ďalej je významný fakt, že zlúčenina podlá vynálezu plné inhibuje rozmnožovanie kvasinky Saccharomyces cerevisiae už v koncentrácii 62,5.10-6 mól dm-3.Significantly, the compound of the invention has a new, hitherto unknown structure and fully inhibits the growth and multiplication of the tested anaerobically sporulating Clostridium bacteria at a concentration of 500.10 -6 mol dm -3 . Furthermore, it is significant that the compound according to the invention fully inhibits the multiplication of the yeast Saccharomyces cerevisiae even at a concentration of 62.5.10 -6 mol dm -3 .
Zlúčeninu podlá vynálezu možno používat ako účinnú zložku antibakteriálnych a protikvasínkových prípravkov a to samostatné, alebo v zmesi s inými látkami, ďalej ju možno používat ako reaktívny produkt pře ďalšie syntézy.The compound of the present invention can be used as an active ingredient of antibacterial and anti-yeast preparations alone or in a mixture with other substances, and can be used as a reactive product for further syntheses.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS555989A CS275631B6 (en) | 1989-09-29 | 1989-09-29 | 6-Amino-2- (3-pentylthio) benzothiazole |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS555989A CS275631B6 (en) | 1989-09-29 | 1989-09-29 | 6-Amino-2- (3-pentylthio) benzothiazole |
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| Publication Number | Publication Date |
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| CS8905559A1 CS8905559A1 (en) | 1990-12-13 |
| CS275631B6 true CS275631B6 (en) | 1992-03-18 |
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| CS555989A CS275631B6 (en) | 1989-09-29 | 1989-09-29 | 6-Amino-2- (3-pentylthio) benzothiazole |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180000793A1 (en) * | 2015-02-06 | 2018-01-04 | Ernesto Abel-Santos | Inhibiting Germination of Clostridium Perfringens Spores to Reduce Necrotic Enteritis |
| USRE49949E1 (en) | 2012-08-13 | 2024-04-30 | The Board Of Regents Of The Nevada System Of Higher Education On Behalf Of The University Of Nevada, Las Vegas | Reducing risk of contracting clostridium-difficile associated disease |
| US12220421B2 (en) | 2021-09-09 | 2025-02-11 | The Boards Of Regents Of The Nevada System Of Higher Education On Behalf Of The University Of Nevada, Las | Inhibitors of C. difficile spore germination |
-
1989
- 1989-09-29 CS CS555989A patent/CS275631B6/en unknown
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE49949E1 (en) | 2012-08-13 | 2024-04-30 | The Board Of Regents Of The Nevada System Of Higher Education On Behalf Of The University Of Nevada, Las Vegas | Reducing risk of contracting clostridium-difficile associated disease |
| US20180000793A1 (en) * | 2015-02-06 | 2018-01-04 | Ernesto Abel-Santos | Inhibiting Germination of Clostridium Perfringens Spores to Reduce Necrotic Enteritis |
| US10945996B2 (en) | 2015-02-06 | 2021-03-16 | The Board Of Regents Of The Nevada System Of Higher Education On Behalf Of The University Of Nevada, Las Vegas | Inhibiting germination of clostridium perfringens spores to reduce necrotic enteritis |
| US20210228550A1 (en) * | 2015-02-06 | 2021-07-29 | The Board Of Regents Of The Nevada System Of Higher Education On Behalf Of The University Of Nevada | Inhibiting Germination of Clostridium Perfringens Spores to Reduce Necrotic Enteritis |
| US12144800B2 (en) * | 2015-02-06 | 2024-11-19 | The Board Of Regents Of The Nevada System Of Higher Education On Behalf Of The University Of Nevada, Las Vegas | Inhibiting germination of Clostridium perfringens spores to reduce necrotic enteritis |
| US12220421B2 (en) | 2021-09-09 | 2025-02-11 | The Boards Of Regents Of The Nevada System Of Higher Education On Behalf Of The University Of Nevada, Las | Inhibitors of C. difficile spore germination |
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| Publication number | Publication date |
|---|---|
| CS8905559A1 (en) | 1990-12-13 |
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