CS277475B6 - 6-Acetamido-2- (2,4-dinitrophenylthio) benzothiazole and its method of preparation - Google Patents
6-Acetamido-2- (2,4-dinitrophenylthio) benzothiazole and its method of preparation Download PDFInfo
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- CS277475B6 CS277475B6 CS897014A CS701489A CS277475B6 CS 277475 B6 CS277475 B6 CS 277475B6 CS 897014 A CS897014 A CS 897014A CS 701489 A CS701489 A CS 701489A CS 277475 B6 CS277475 B6 CS 277475B6
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Abstract
Bol připravenýdoterazneznámy 6-acetamido-2- /2,4-dinitrofenyltio/benzotiazol. Syntéza uvedenej zlúčeniny sa uskutočňuje reakciou 6- amino-2- / 2,4-dinitrofenyltio/benzotiazolu s acetanhydridom pri teplote miestnosti. Zlúčenina je antibakteriálne účinná proti grampozitívnym a gramnegatívnym baktériám, pričom najvyššiu účinnosí prejavila proti Bacillus subtilis a klinickému patogénu Próteus vulgaris.The previously unknown 6-acetamido-2- /2,4-dinitrophenylthio/benzothiazole was prepared. The synthesis of the above compound is carried out by the reaction of 6- amino-2- /2,4-dinitrophenylthio/benzothiazole with acetic anhydride at room temperature. The compound is antibacterially active against gram-positive and gram-negative bacteria, with the highest activity against Bacillus subtilis and the clinical pathogen Proteus vulgaris.
Description
1 CS 277475 B6
Oblast techniky
Vynález sa týká 6-acetamido-2-/2,4-dinitrofenyltio/benzo-tiazolu a spósobu jeho přípravy.
Potěrajší stav techniky
Doteraz boli známe antimykobakteriálne a antihelmintickyúčinné 6-acetamido-2-alkyltiobenzotiazoly /Chem. Zvěsti, 39,1985,Sidóová E., Odlerová Ž. a Špaldonová R., str. 543/.
Podstata vynálezu
Predmetom vynálezu je 6-acetamido-2-alkyltiobenzotiazolvzorca I
ktorý je antibakteriálne účinný proti grampozitívnym a gramnega-tívnym baktériám. Ďalej je predmetom vynálezu spósob přípravyzlúčeniny vzorca I, ktorý sa vyznačuje tým, že 6-amino-2-/2,4-di-nitrofenyltio/benzotiazol reaguje s acetanhydridom pri teplotemiestnosti. Příklad uskutočnenia vynálezu Příprava 6-acetamido-2-/2,4-dinitrofenyltio/benzotiazolu 6-Amino-2-/2,4-dinitrofenyltio/benzotiazol /3,5 g, 0,01 mol/ rea- *5 goval s acetanhydridom /10 cm , 10,85 g, 0,106 mol/ pri teplotemiestnosti 1 hodinu. Potom sa reakčná zmes doplnila vodou na ob-jem 150 cm3, zahriala sa do varu a potom odstavila na 30 minútpri teplote miestnosti. Získal sa tuhý produkt zlatožltej farbys t.t. 241,5 až 253,5 °C v množstve 3,6 g /92,3 %/, ktorý okrem edokladného premývania vodou nevyžadoval ďalsie čistenie. M.h. = 390,40 4
Pre C15H10N4O5S2 vypočítané % : C 46,15 H 2,58 N 14,35 S 16,43 zistené % : 46,12 '2,54 14,32 16,34 Příklad 2
Antibakteriálna účinnost zlúčeniny podía vynálezuBola starjovená antibakteriálna účinnost zlúčeniny podlá vynálezu proti 3 zástupcom grampozitívnych a 3 zástupcom gram-negatívnych baktérií. CS 277475 B6 2
Mikroorganizmy boli kultivované v másopeptonovom bujóne zaintenzívnej aerácie a za optimálnej teploty /37 °C resp. 25 °C/.Mikroorganizmy boli v stálom styku so zlúčeninou podlá vynálezu,ktorá bola přidávaná v koncentrácii 1.10-3, 2.10-4, 4.10-^ a 8.10 mol dm , rozpuštěna v takom množstve dimethylsulfoxidu,aby toto nepřesahovalo 1 % kultivačněj pódy. Účinok bol posudzo-vaný na základe ovplyvnenia rastu a rozmnožovania buniek foto-metrickým meranim zákalu oproti kontrole, v pravidelných časovýchintervaloch. Z nameraných hodnot boli zostrojené rastové křivkya z nich sa matematicko-graficky získali hodnota ED50 a ED100 čo představuje zabrzdenie rastu a rozmnožovania buniek na 50 resp.100 %.
Tabulka a/ k příkladu 2
Antibakteriálna účinnost zlúčeniny podlá vynálezu proti gram-pozitívnym baktériám
Micrococcus luteus 10-3mol dm-3
ED 50 / μg cm'ED100
Bacillus subtilis Staphylococcusaureus 10-3mol dm-3/ μg cm-3 10-3mol dm-3/ μgcm'ED50 ED100 ED50 ED100 1,78 35,50 0,08 0,695 13,86 0,03 0,60 0,40 11,00 0,23 0,16 4,29
Tabulka b/ k příkladu 2
Antibakteriálna účinnost zlúčeniny podlá vynálezu proti gram-negatívnym baktériám
Próteus vulgaris10-3mol dm-3^g cm-3 Pseudomonans aeruginosa10-3mol dm-3^g cm-3 Escherichia coli 10-3mol ed50 dm Aig cmED100 ED50 ED100 ed50 ED100 0,003 0,007 8,91 39,80 0,20 2,51 0,001 0,003 3,48 15,54 0,08 0,98 Významný je fakt, že zlúčenina podlá vynálezu je novej, do-teraz neznámej štruktúry a prejavila antibakteriálnu účinnostproti všetkým testovaným zástupcom grampozitívnych a gramnegatív-nych bakérií. Ďalej významný je fakt, že zlúčenina prejavila vy-sokú účinnost proti G+ baktériám Bacillus subtilis /ED50 =7,58.10"”^mol dm-3 a Εϋ-^θθ = 6,03.10-^mol dm-3/. Zvlášt významný je fakt, že zlúčenina podlá vynálezu je vysoko účinná proti G-baktériám Próteus vulgaris, ktorý sa uplatňuje ako klinický pato-gén /ED50 = 3,02.10-6mol dm-3 a ED100 = 7,08.10-6mol dm-3/.
Zlúčeninu podlá vynálezu možno používat ako účinnú zložkuantibakteriálnych prípravkov a dezinfektantov samostatné, alebov zmesi s inými látkami, alebo ako medziprodukt pre.ďalšie synté-zy·
1 CS 277475 B6
Technical field
The invention relates to 6-acetamido-2- (2,4-dinitrophenylthio) benzothiazole and to a process for its preparation.
The better state of the art
To date, antimycobacterial and antihelmintic-active 6-acetamido-2-alkylthiobenzothiazoles / Chem. Zvěsti, 39, 1985, Sidóová E., Odlerová Ž. and Špaldonová R., p. 543].
SUMMARY OF THE INVENTION
The present invention relates to 6-acetamido-2-alkylthiobenzothiazolorca I
which is antibacterially active against Gram-positive and Gram-negative bacteria. The present invention further provides a process for the preparation of a compound of formula I, characterized in that 6-amino-2- (2,4-di-nitrophenylthio) benzothiazole is reacted with acetic anhydride at room temperature. Example Preparation of 6-acetamido-2- (2,4-dinitrophenylthio) benzothiazole 6-Amino-2- (2,4-dinitrophenylthio) benzothiazole (3.5 g, 0.01 mol) was reacted with acetic anhydride (10 cm, 10.85 g, 0.106 mol) at a temperature of 1 hour. Then, the reaction mixture was made up to 150 cm 3 with water, heated to boiling, and then set aside for 30 minutes at room temperature. A golden-yellow solid solid product of 241.5 to 253.5 ° C was obtained in an amount of 3.6 g (92.3%), which required no further purification in addition to fine water washing. Mh = 390.40 4
C15H10N4O5S2 calculated%: C 46.15 H 2.58 N 14.35 S 16.43 found%: 46.12 '2.54 14.32 16.34 Example 2
Antibacterial Activity of the Compound of the Invention The antibacterial activity of the compound of the invention against the 3 representatives of Gram-positive and 3 representatives of Gram-negative bacteria was aged. CS 277475 B6 2
Microorganisms were cultured in Butopepton broth with intense aeration and at an optimum temperature of 37 ° C. The microorganisms were in constant contact with the compound of the invention which was added at a concentration of 1.10-3, 2.10-4, 4.10- and 8.10 mol dm in an amount of dimethylsulfoxide to not exceed 1% of the culture grade. The effect was assessed by influencing the growth and multiplication of cells by photometric measurement of haze over control, at regular time intervals. Growth curves were constructed from the measured values, and ED50 and ED100 were mathematically and graphically obtained, representing a growth inhibition and cell multiplication of 50 and 100%, respectively.
Table a / to Example 2
Antibacterial activity of the compound of the invention against gram-positive bacteria
Micrococcus luteus 10-3mol dm-3
ED 50 / μg cm'ED100
Bacillus subtilis Staphylococcusaureus 10-3mol dm-3 / μg cm-3 10-3mol dm-3 / μgcm'ED50 ED100 ED50 ED100 1.78 35.50 0.08 0.695 13.86 0.03 0.60 0.40 11 , 00 0.23 0.16 4.29
Table b / Example 2
Antibacterial activity of the compound of the invention against gram-negative bacteria
Proteus vulgaris10-3mol dm-3 ^ g cm-3 Pseudomonans aeruginosa10-3mol dm-3 ^ g cm-3 Escherichia coli 10-3mol ed50 dm Aig cmED100 ED50 ED100 ed50 ED100 0.003 0.007 8.91 39.80 0.20 2, 51 0.001 0.003 3.48 15.54 0.08 0.98 Significant is the fact that the compound of the invention is a new, up to now unknown structure and has shown antibacterial activity against all tested Gram-positive and Gram-negative bakers. Also noteworthy is that the compound exhibited high activity against G + bacteria Bacillus subtilis (ED 50 = 7.58.10 µmole dm-3 and εϋ-θθ = 6.03.10 µmol dm-3). the fact that the compound of the invention is highly potent against G-bacteria Proteus vulgaris, which acts as a clinical pathogen (ED 50 = 3.02.10-6mol dm-3 and ED100 = 7.08.10-6mol dm-3).
The compound of the present invention can be used as an effective component antibacterial agent and disinfectant alone, or as a mixture with other agents, or as an intermediate for further synthesis.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS897014A CS277475B6 (en) | 1989-12-12 | 1989-12-12 | 6-Acetamido-2- (2,4-dinitrophenylthio) benzothiazole and its method of preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS897014A CS277475B6 (en) | 1989-12-12 | 1989-12-12 | 6-Acetamido-2- (2,4-dinitrophenylthio) benzothiazole and its method of preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS701489A3 CS701489A3 (en) | 1992-11-18 |
| CS277475B6 true CS277475B6 (en) | 1993-03-17 |
Family
ID=5418489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS897014A CS277475B6 (en) | 1989-12-12 | 1989-12-12 | 6-Acetamido-2- (2,4-dinitrophenylthio) benzothiazole and its method of preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS277475B6 (en) |
-
1989
- 1989-12-12 CS CS897014A patent/CS277475B6/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS701489A3 (en) | 1992-11-18 |
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