Oriental Pharmacy and Experimental Medicine

, Volume 12, Issue 2, pp 141–150 | Cite as

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

  • Meenakshi Agrawal
  • Sonika Jain
  • Anshu Agarwal
  • Jaya Dwivedi
  • Swapnil Sharma
  • D. Kishore
Research Article
First Online:
Received:
Accepted:

Abstract

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.

Keywords

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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Notes

Acknowledgement

Authors are grateful to the Director CDRI Lucknow (India) (for providing the spectral data of the compounds), to the Head Department of Bioscience and Biotechnology, of Banasthali University (for providing the results of the antimicrobial screening) and to the Head Department of Bioscience and Biotechnology, of PBRI Bhopal (India) (for providing the results of CNS depressant activity). Authors are thankful to Department of Science and Technology (DST) New-Delhi (India) for providing financial assistance to (Banasthali Centre for Education and Research in Basic Sciences) under their CURIE (Consolidation of University Research for innovation and Excellence in Women University) programme.

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Copyright information

© Institute of Oriental Medicine, Kyung Hee University 2012

Authors and Affiliations

  • Meenakshi Agrawal
    • 1
  • Sonika Jain
    • 1
  • Anshu Agarwal
    • 1
  • Jaya Dwivedi
    • 1
  • Swapnil Sharma
    • 2
  • D. Kishore
    • 1
  1. 1.Department of ChemistryBanasthali UniversityBanasthaliIndia
  2. 2.Department of PharmacyBanasthali UniversityBanasthaliIndia

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