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Synthesis and antibacterial activity of N 1-(carbazol-3-yl)amidrazones incorporating piperazines and related congeners

Synthesis and antibacterial activity of N 1-(carbazol-3-yl)amidrazones incorporating piperazines... Abstract A selected set of N 1-(4-chloro-9-ethylcarbazol-3-yl)amidrazones ( 7a–n ) has been synthesized by reacting the respective hydrazonoyl chloride 5 derived from 3-amino-9-ethylcarbazole ( 3 ), with an appropriate sec -cyclic amine ( 6a–n ) in ethanol in the presence of triethylamine. Unexpectedly, aromatic ring chlorination occurred at C-4 of 3 during its conversion to 6 as evidenced by analytical and spectral data and further confirmed by single crystal X-ray structure determination of the amidrazone 7n . Compounds 7a–n were tested for their in vitro antibacterial activity. Among the tested bacterial strains, methicillin-resistant Staphylococcus aureus was the most susceptible to 7f and Bacillus cereus to 7b both with a minimum inhibitory concentration value of 1.56 µg mL −1 . Compounds 7c , 7f , and 7h could be useful as lead structures for further development of new antibacterial agents against Gram-positive and Gram-negative pathogens. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Zeitschrift für Naturforschung B de Gruyter

Synthesis and antibacterial activity of N 1-(carbazol-3-yl)amidrazones incorporating piperazines and related congeners

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References (27)

Publisher
de Gruyter
Copyright
Copyright © 2016 by the
ISSN
0932-0776
eISSN
1865-7117
DOI
10.1515/znb-2016-0043
Publisher site
See Article on Publisher Site

Abstract

Abstract A selected set of N 1-(4-chloro-9-ethylcarbazol-3-yl)amidrazones ( 7a–n ) has been synthesized by reacting the respective hydrazonoyl chloride 5 derived from 3-amino-9-ethylcarbazole ( 3 ), with an appropriate sec -cyclic amine ( 6a–n ) in ethanol in the presence of triethylamine. Unexpectedly, aromatic ring chlorination occurred at C-4 of 3 during its conversion to 6 as evidenced by analytical and spectral data and further confirmed by single crystal X-ray structure determination of the amidrazone 7n . Compounds 7a–n were tested for their in vitro antibacterial activity. Among the tested bacterial strains, methicillin-resistant Staphylococcus aureus was the most susceptible to 7f and Bacillus cereus to 7b both with a minimum inhibitory concentration value of 1.56 µg mL −1 . Compounds 7c , 7f , and 7h could be useful as lead structures for further development of new antibacterial agents against Gram-positive and Gram-negative pathogens.

Journal

Zeitschrift für Naturforschung Bde Gruyter

Published: Aug 1, 2016

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