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KMID : 1200820120120020141
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Oriental Pharmacy and Experimental Medicine
2012 Volume.12 No. 2 p.141 ~ p.150
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Application of novel precursors derived from carbazolo condensed azepinones to the direct single step synthesis of corresponding isoxazole and pyrazole annulated analogues of medicinal importance
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Agrawal Meenakshi
Jain Sonika
Agarwal Anshu
Dwivedi Jaya
Sharma Swapnil
Kishore D.
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Abstract
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Exceedingly facile protocols based on the reactivity of corresponding oxoketenedithioacetal (4), 2-(dimethylaminomethylene) ketone (5), β-oxoenolether (6) and α, β-unsaturated ketone (7) resulted from 7-ethyl-3,4 dihydroazepino[3,2-b] carbazole-2,5 (1H,7H)-dione (3) on its reaction with base catalyzed condensation of (a) CS2+ MeI (b) DMF-DMA (c) H-COOEt and (IV) C6H5CHO respectively, has been explored to provide an easy access of their isoxazole and pyrazole annulated analogues (8?13) of medicinal interest. The key compound 3 from which, the synthesis proceeded was in turn realized on the reaction of commercial 3-amino-9-ethyl carbazole (1) with ethyl succinyl chloride, under the conditions of Friedel-Crafts acylation followed by cyclocondensation of the resulting intermediate 2 with PPA. Isoxazolo and pyrazolo annulated analogues of carbazolo condensed azepinone derivatives (8?13) were screened for their in-vitro antimicrobial potential against various bacterial and fungal species. Besides this pyrazole derivative (8) was also evaluated for its CNS depressant potential in mice using photoactometer.
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KEYWORD
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Friedel-Crafts acylations, 3-amino-9-ethyl carbazole, Ethyl ester of succinyl chloride, Oxoketnedithioacetal, 2-(dimethylaminomethylene) ketone, Dimethyl formamide dimethyl acetal, Oxoenolether, Chalcone, Isoxazole, Pyrazole
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