CS276191B6 - 6- (Bicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) -3-hydroxymethyl-2-benzothiazolione - Google Patents
6- (Bicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) -3-hydroxymethyl-2-benzothiazolione Download PDFInfo
- Publication number
- CS276191B6 CS276191B6 CS903527A CS352790A CS276191B6 CS 276191 B6 CS276191 B6 CS 276191B6 CS 903527 A CS903527 A CS 903527A CS 352790 A CS352790 A CS 352790A CS 276191 B6 CS276191 B6 CS 276191B6
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- dicarboximido
- ene
- hept
- bicyclo
- hydroxymethyl
- Prior art date
Links
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Bol připravený doteraz neznámy 6-/bicyklo ’ /2.2.l/hept-5-en-2,3-dikarboximido/-3-hydroxymetýl-2-benzotiazolíntión. Syntéza uvedenej zlúčeniny sa uskutočňuje reakciou 6-/bicyklo/2.2.l/hept-5-en-2,3-dikarboximido/-2- -benzotiazolíntiónu s formaldehydom v organickom rozpúštadle za varu. Zlúčenina je antibakteriálne účinná proti anaeróbnym sporulujúcim baktériám rodu'Clostridium a zároveň je reaktívnym medziproduktom pre syntézu zlú čenín s předpokládanou biologickou aktivitou.The previously unknown 6-/bicyclo ’ /2.2.l/hept-5-ene-2,3-dicarboximido/-3-hydroxymethyl-2-benzothiazolinethione was prepared. The synthesis of the above compound is carried out by the reaction of 6-/bicyclo /2.2.l/hept-5-ene-2,3-dicarboximido/-2- -benzothiazolinethione with formaldehyde in an organic solvent at boiling temperature. The compound is antibacterially effective against anaerobic sporulating bacteria of the genus Clostridium and is also a reactive intermediate for the synthesis of compounds with presumed biological activity.
Description
Predmetom vynálezu je 6-Zbicyklo/Ž.2. l/hept-5-en-2,3-dikarboximidoZ-3-hydroxymetyl-2-benzotiazolíntión. 'The subject of the invention is 6-Zbicyclo / Z.2. 1 / hept-5-ene-2,3-dicarboximido-2-hydroxymethyl-2-benzothiazolinethione. '
Doteraz bol známy 6-cinnamylidénamino-2-benzotiazolíntión, ktorý prejavil účinnost proti anaeróbnym sporulujúcim baktériám rodu Clostridium.Until now, 6-cinnamylideneamino-2-benzothiazolinethione has been known to be effective against anaerobic sporulating bacteria of the genus Clostridium.
Teraz sme zistili, že doteraz neznáma zlúčenina vzorcaWe have now found that a hitherto unknown compound of the formula
je antibakteriálne účinná proti anaeróbnym sporulujúcim baktériám rodu Clostridium.is antibacterially active against anaerobic sporulating bacteria of the genus Clostridium.
Súčasne bol zistený sposob přípravy uvedenej zlúčeniny reakciou 6-/bicykloZ2.2.17hept-5-en-2,3-dikarboximido/-2-benzotiazolíntiónu (Sidóová, E., Čs. autorského osvedčenia č. 195150 /1979/.) s formaldehydom v etanole zahriatím do varu.At the same time, a method for preparing the title compound by reacting 6- (bicyclo [2.2.17] hept-5-ene-2,3-dicarboximido) -2-benzothiazolinethione (Sidóová, E., Czech Author's Certificate No. 195150 (1979)) with formaldehyde was discovered. in ethanol by heating to boiling.
Nasledujúce příklady bližšie osvetlujú, ale nijako neobmedzujú přípravu a vlastnosti zlúčeniny podlá vynálezu.The following examples illustrate, but do not limit, the preparation and properties of the compound of the invention.
Příklad 1 .Example 1.
Příprava 6-/bicyklo/2.2.17hept-5-en-2,3-dikarboximid/-3-hydroxymetyl-2-benzotiazolíntiónuPreparation of 6- (bicyclo) 2.2.17hept-5-ene-2,3-dicarboximide--3-hydroxymethyl-2-benzothiazolinethione
6-/bicykloZ'2.2.17hept-5-en-2,3-dikarboximido/-2-benzotiazolíntión (9,85 g, 0,03 mol) a30 %ný formaldehyd (12 cm , 0,06 mol) bolí spolu zahriate v etanole (150 cm ) do varu až do rozpustenia tuhej fázy. Po odfarbení aktívnym uhlím a ochladení filtrátu na teplotu miestnosti sa vylúčil z roztoku krystalický ó-Zbicyklo/Z . 2.17hept-5-en-2,3-dikarboximidoZ-3-hydroxymetyl-2-benzotiazolíntión v množstve 9,25 g (86,1 %), ktorý nevyžadoval áalšie čistenie.6- [Bicyclo [2.2.17] hept-5-ene-2,3-dicarboximido] -2-benzothiazolinethione (9.85 g, 0.03 mol) and 30% formaldehyde (12 cm, 0.06 mol) were heated together. in ethanol (150 cm) to boiling until the solid dissolves. After decolorization with activated carbon and cooling of the filtrate to room temperature, crystalline δ-Zbicyclo / Z precipitated out of solution. 2.17hept-5-ene-2,3-dicarboximido-2-hydroxymethyl-2-benzothiazolinethione in an amount of 9.25 g (86.1%), which did not require further purification.
M.h. = 358,44M.h. = 358.44
Pre vypočítané %; C 56,97 H 3,94 N 7,82 S 17,89 zistené % : 56,81 3,90 7,64 17,90For calculated%; C 56.97 H 3.94 N 7.82 S 17.89 found%: 56.81 3.90 7.64 17.90
Příklad 2Example 2
Antibakteriálna aktivita zlúčeniny podlá vynálezu proti vybraným zástupcem anaerobně -6 '-3 sporulujúcich baktérií rodu Clostridium (10 mol dm ) v porovnaní s účinnosťou 2-merkaptobenzotiazolu (2-MBT).The antibacterial activity of the compound of the invention against selected representatives of the anaerobically -6 '-3 sporulating bacteria of the genus Clostridium (10 mol dm) compared to the activity of 2-mercaptobenzothiazole (2-MBT).
MIC = minimálna inhibičná koncentrácia Znajnižšia koncentrácia zo skúšaných koncentrácií látok, ktorá plné inhibuje rast a rozmnožovanie testovaných druhov klostrídií.MIC = Minimum Inhibitory Concentration The lowest concentration of 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 rozmnožovanie anaeróbnych sporulujúcich baktérií rodu Clostridium sa zisťoval agarovou metodou na tuhých živných půdách s různou koncentráciou pridanej študovanej látky. Látka bola rozpuštěná v dimetylsulfoxide. Koncentrácia rozThe effect of the study substance on the growth and multiplication of anaerobic sporulating bacteria of the genus Clostridium was determined by the agar method on solid nutrient media with different concentrations of added study substance. The substance was dissolved in dimethyl sulfoxide. Concentration of div
CS 276 191 B6 púšťadla v kultivačnej půdě nepřekročila 1 %. Použité kultivačně půdy: Vl agar a MíillerHintonov agar (komerčně výrobky Imuny, n.p. Šarišské Michal’any), VL agar a Miiller-Hintonov agar obohatený o 5 % def ibrinovanej konskej krvi. Analogicky boli 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.CS 276 191 B6 solvents in the culture medium did not exceed 1%. Culture media used: VL agar and Miller-Hinton agar (commercial products of Imuna, n.p. Šarišské Michal’any), VL agar and Miller-Hinton agar enriched with 5% defibrinated horse blood. Analogously, control soils were inoculated 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 podl’a vynálezu je novej, doteraz neznámej struktury a plné inhibuje rast a rozmnožovanie testovaných anaeróbnych sporulujúcich baktérií rodu Clostridium v koncentrácii 1000. lO^mól drn”2 3. Zvlášť významný je fakt, že zlúčenina podl’a vynálezu obsahuje Cf^OH skupinu na dusíkovom atome heterocyklu a takto představuje nový reaktívny medziprodukt pře syntézu biologicky aktívnych látok, najma Mannichovou reakciou.Important is that the compound of the invention is a new, previously unknown structure and a fully inhibits growth and reproduction of the test sporulated anaerobic bacteria Clostridium 1000 at a concentration of lO ^ mol turf "2 3rd Of particular importance is the fact that the compound of the invention contains a C 1-4 OH group on the nitrogen atom of the heterocycle and thus represents a new reactive intermediate for the synthesis of biologically active substances, in particular by the Mannich reaction.
Zlúčeninu podl’a vynálezu možno používat’ ako účinnú zložku antibakteriálnych prípravkov samostatné, alebo v zmesi s inými látkami, dalej 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, further as an intermediate for further syntheses.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS903527A CS276191B6 (en) | 1990-07-17 | 1990-07-17 | 6- (Bicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) -3-hydroxymethyl-2-benzothiazolione |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS903527A CS276191B6 (en) | 1990-07-17 | 1990-07-17 | 6- (Bicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) -3-hydroxymethyl-2-benzothiazolione |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS352790A3 CS352790A3 (en) | 1992-04-15 |
| CS276191B6 true CS276191B6 (en) | 1992-04-15 |
Family
ID=5375636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS903527A CS276191B6 (en) | 1990-07-17 | 1990-07-17 | 6- (Bicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) -3-hydroxymethyl-2-benzothiazolione |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS276191B6 (en) |
-
1990
- 1990-07-17 CS CS903527A patent/CS276191B6/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS352790A3 (en) | 1992-04-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Chain et al. | An antibacterial substance produced by Penicillium claviforme | |
| Nishimura et al. | Toyocamycin, a new anti-candida antibiotics | |
| Kamalakannan et al. | Synthesis and characterization of cobalt and nickel chelates of 5-dimethylaminomethyl-2-thiouracil and their evaluation as antimicrobial and anticancer agents | |
| Anzai et al. | The new antibiotics, questiomycins A and B | |
| Ikawa et al. | Synthesis and biological activity of homologs of pyridoxal and pyridoxamine | |
| Duclos et al. | Ring opening of thiamine analogs. Role of ring opening in physiological function | |
| JPH044871B2 (en) | ||
| Strelitz et al. | Aklavin, an antibiotic substance with antiphage activity | |
| JPS62181281A (en) | Large ring antibiotic and its production | |
| Happold et al. | The Coli-Tryptophan-Indole Reaction: II. The Non-Production of Tryptophanase in Media Containing Glucose | |
| Raistrick | On a new type of chemical change produced by bacteria. The conversion of histidine into urocanic acid by bacteria of the coli-typhosus group | |
| Wada et al. | A new thiamine derivative, S-benzoylthiamine O-monophosphate | |
| CS276191B6 (en) | 6- (Bicyclo [2.2.1] hept-5-ene-2,3-dicarboximido) -3-hydroxymethyl-2-benzothiazolione | |
| Katznelson | Production of pyruvate from 6-Phospho-gluconate by bacterial plant pathogens and legume bacteria | |
| US4713372A (en) | 2-chloropentostatin compound having adenosine diaminase inhibitory activity | |
| US4005076A (en) | Hydrazones of 3-formylrifamycin SV | |
| Sethunathan | Biodegradation of diazinon in paddy fields as a cause of its inefficiency for controlling brown planthoppers in rice fields | |
| EP0156524A2 (en) | 2'-Chloropentostatin, a pharmaceutical composition comprising the compound and a novel microorganism for producing the compound | |
| CS275632B6 (en) | 6-C3 Nnamylideneamino-2-ethylthienzothiazole | |
| US4959370A (en) | Alkaloids of marine origin | |
| Anzai et al. | A new antibiotic bovinocidin, identified as β-nitropropionic acid | |
| CS276501B6 (en) | 6-Cinnamylideneamino-2-benzothiazolinothion · | |
| BARONE et al. | A 2-Trifluoromethyl Analog of Thiamin1 | |
| US3829417A (en) | Imidazole substituted rifamycins | |
| US3704290A (en) | 6-(1 - substituted aminocycloalkane-carboxamido)-penicillanic acid and salts |