Original title: Nové skupiny potenciálních antituberkulotik s thioxo skupinou
Translated title: New groups of potential antituberculotics with thioxo group
Authors: Husáková, Petra ; Waisser, Karel (advisor) ; Kolář, Karel (referee)
Document type: Rigorous theses
Year: 2008
Language: cze
Abstract: [cze] [eng]
9.2. ČESKÝ ABSTRAKT V rigorózní práci byl popsán vliv záměny oxo skupiny za thioxoskupinu v řadě halogenovaných 3-(4-ethylfenyl)benzoxazin-2,4(3H)-dionů a 6-chlor-3-(4-butyfenyl)benzoxazin-2,4(3H)-dionů Výchozí ethyl (nebo butyl) salicylanilidy byly syntetizovány z ethyl (nebo butyl) anilinu a substituované salicylové kyseliny v toluenu za přítomnosti chloridu fosforitého. (Skupina halogenovaných salicylových kyselin: 4-chlor-, 5-chlor-, 5-brom- and 3,5-dibrom salicylová kyselina.) Halogenované 4'-ethylsalicylanilidy reagovaly v suchém pyridinu s methyl- chloroformiatem za vzniku 3-(4-ethylfenyl)benzoxazin-2,4(3H)-dionů. Podobně byly připraveny 6-chlor-3-(4-butylfenyl)benzoxazin-2,3,(4-H)-diony. Směs 3-(4-ethyfenyl)-4-thioxo-2H-1,3- benzoxazin-2(3H)-onu a 3-(4-ethylfenyl)-2H-1,3-benzoxazin-2,4(3H)-dithionu byla připravena reakcí halogenovaných 3-(4-ethylfenyl)- 2H-1,3-benzoxazin-2,4(3H)-dionů se sulfidem fosforečným. Látky byly odděleny chromatograficky. Podobně byl získán 6-chlor-3-(4- butylfenyl)-thioxo-2H-1,3-benzoxazin-2(3H)-on a 6-chlor-3-(4-butylfenyl)-2H-1,3-benzoxazin- 2,4(3H)-dithion. Látky byly hodnoceny in vitro na antimykobakteriální aktivitu vůči Mycobacterium tuberculosis, M. kansasii (dva kmeny) a M. avium. Thioxo (nebo dithioxo) deriváty jsou vysoce aktivními antimykobakteriálními látkami,... . ENGLISH ABSTRACT In the rigorous thesis are described the influence of replacement oxo group for thioxo group in the series of halogenated 3-(4-ethylphenyl)benzoxazine-2,4(3H)-diones and 6-chloro-3- (4-butylphenyl)benzoxazine-2,4(3H)-dione. The starting ethyl (or butyl) salicylanilides were synthesis from substituted salicylic acid and ethyl (or butyl) aniline in toluene by the presence of phosphorus trichloride. (The set of halogenated salicyl acids compounds: 4-chloro-, 5-chloro-, 5- bromo- and 3,5-dibromosalicylic acid). The halogenated 4'-ethylsalicylanilides were reacted in dry pyridine with methyl-chloroformiate to form 3-(4-ethylphenyl)benzoxazine-2,4(3H)-diones. Similar were prepared 6-chloro-3-(4-butylphenyl)benzoxazine-2,4(3H)-diones. The mixture of 3- (4-ethyphenyl)-4-thioxo-2H-1,3-benzoxazine-2(3H)-one and 3-(4-ethylphenyl)-2H-1,3- benzoxazine-2,4(3H)-dithione was prepared by the reaction of the halogenated 3-(4- ethylphenyl)- 2H-1,3-benzoxazine-2,4(3H)-diones with phosphorus pentasulfide. The products were separated by chromatography. The 3-(4-ethylphenyl)-6-chloro-4-thioxo-2H-1,3- benzoxazine-2(3H)-ones and 6-chloro-3-(4-ethylphenyl)-2H-1,3-benzoxazine-2,4(3H)-dithiones were prepared by similar way. The compounds were tested in vitro for antimycobacterial activity against Mycobacterium...

Institution: Charles University Faculties (theses) (web)
Document availability information: Available in the Charles University Digital Repository.
Original record: http://hdl.handle.net/20.500.11956/19306

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