We report the novel synthesis of azetidin-2-one derivatives containing aryl sulfonate moiety from the reaction of 2-hydroxy benzaldehyde with p-toluene sulfonyl chloride afforded firstly 2-formylphenyl 4-methylbenzene...We report the novel synthesis of azetidin-2-one derivatives containing aryl sulfonate moiety from the reaction of 2-hydroxy benzaldehyde with p-toluene sulfonyl chloride afforded firstly 2-formylphenyl 4-methylbenzene sulfonate (2). The compound (2) on reaction with p-aminobenzoic acid or 2-aminopyridine gave the corresponding aldimines (3). Furthermore, the aldimines are on reaction with chloroacetyl chloride gives corresponding azetidin-2-ones in good to moderate yield. Among the eight synthesized azetidin-2-ones, five selected compounds have been screened for the an-ti-inflammatory activity, few of them showed good anti-inflammatory activity compared with standard drugs. Anti- microbial activity of all synthesized compounds has been tested and most of the compounds showed good anti-bacterial and anti-fungal activities.展开更多
The most important nitrogen containing heterocycles of pyridine containing substituted phenyl azetidine-2-ones have found pharmacological application such as antibiotics and these compounds also have practical importa...The most important nitrogen containing heterocycles of pyridine containing substituted phenyl azetidine-2-ones have found pharmacological application such as antibiotics and these compounds also have practical importance. The structure of the new derivatives was confirmed by the spectral data and elemental analyses. Out of five new derivatives, three were revealed mild to moderate activity compared with Streptomycin & Fluconazole as a reference standard. Among this new series, 3-chloro-1-(4-fluoro phenyl)/(4-chloro phe-nyl)-4-(pyridine-3-yl) azetidine-2-one (4a & b) were found most activity.展开更多
Syntheses of 4 novel chiral azetidin 2 one derivatives, which were characterized by 1H NMR, IR, specific rotation and elemental analysis, through Staudinger cycloaddition reaction of Schiff base of benzaldehyd...Syntheses of 4 novel chiral azetidin 2 one derivatives, which were characterized by 1H NMR, IR, specific rotation and elemental analysis, through Staudinger cycloaddition reaction of Schiff base of benzaldehyde with chlorine substitution at different position in benzene ring, were described. For the first time, this type of 3 S ,4 R configuration azetidin 2 one mono^crystals with many chiral centers [(3 S ,4 R ) 3 hydroxy N [( S ) (1 phenyl)ethyl ] 4 (2′ chlorophenyl) azetidin 2 one mono^crystal] were obtained, the structures of which were determined by X ray dif fraction analysis. The effects of Schiff base of benzaldehyde with chlorine subs titu tion at different position in benzene ring on stereoselectivity of Staudinger cy cloaddition reaction products were discussed and the results are showed as below : 2 chlorophenyl Schiff base favored to yield 3 S ,4 R configuration prod uct, but 4 chlorophenyl Schiff base favored to yield 3 R ,4 S configuration produc t. The re action orientation of 2,4 dichlorophenyl Schiff base was determined by corporat e effect of 2 and 4 chlorine, and that of the 4 chlorine was more obvious. In co ntrast to 4 chlorophenyl, although the main product was 3 R ,4 S configur ation, 3 chlorophenyl owned lower selectivity.展开更多
文摘We report the novel synthesis of azetidin-2-one derivatives containing aryl sulfonate moiety from the reaction of 2-hydroxy benzaldehyde with p-toluene sulfonyl chloride afforded firstly 2-formylphenyl 4-methylbenzene sulfonate (2). The compound (2) on reaction with p-aminobenzoic acid or 2-aminopyridine gave the corresponding aldimines (3). Furthermore, the aldimines are on reaction with chloroacetyl chloride gives corresponding azetidin-2-ones in good to moderate yield. Among the eight synthesized azetidin-2-ones, five selected compounds have been screened for the an-ti-inflammatory activity, few of them showed good anti-inflammatory activity compared with standard drugs. Anti- microbial activity of all synthesized compounds has been tested and most of the compounds showed good anti-bacterial and anti-fungal activities.
文摘The most important nitrogen containing heterocycles of pyridine containing substituted phenyl azetidine-2-ones have found pharmacological application such as antibiotics and these compounds also have practical importance. The structure of the new derivatives was confirmed by the spectral data and elemental analyses. Out of five new derivatives, three were revealed mild to moderate activity compared with Streptomycin & Fluconazole as a reference standard. Among this new series, 3-chloro-1-(4-fluoro phenyl)/(4-chloro phe-nyl)-4-(pyridine-3-yl) azetidine-2-one (4a & b) were found most activity.
基金ProjectsupportedbytheNationalNaturalScienceofChina (No .2 0 1710 0 8)
文摘Syntheses of 4 novel chiral azetidin 2 one derivatives, which were characterized by 1H NMR, IR, specific rotation and elemental analysis, through Staudinger cycloaddition reaction of Schiff base of benzaldehyde with chlorine substitution at different position in benzene ring, were described. For the first time, this type of 3 S ,4 R configuration azetidin 2 one mono^crystals with many chiral centers [(3 S ,4 R ) 3 hydroxy N [( S ) (1 phenyl)ethyl ] 4 (2′ chlorophenyl) azetidin 2 one mono^crystal] were obtained, the structures of which were determined by X ray dif fraction analysis. The effects of Schiff base of benzaldehyde with chlorine subs titu tion at different position in benzene ring on stereoselectivity of Staudinger cy cloaddition reaction products were discussed and the results are showed as below : 2 chlorophenyl Schiff base favored to yield 3 S ,4 R configuration prod uct, but 4 chlorophenyl Schiff base favored to yield 3 R ,4 S configuration produc t. The re action orientation of 2,4 dichlorophenyl Schiff base was determined by corporat e effect of 2 and 4 chlorine, and that of the 4 chlorine was more obvious. In co ntrast to 4 chlorophenyl, although the main product was 3 R ,4 S configur ation, 3 chlorophenyl owned lower selectivity.
