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Synthesis, Characterization, and Bioactivity of Novel Bicinnolines Having 1‐Piperazinyl Moieties
Author(s) -
AlQtaitat Malath A.,
ElAbadelah Mustafa M.,
Sabri Salim S.,
Matar Suzan A.,
Hammad Hana M.,
Mubarak Mohammad S.
Publication year - 2019
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3390
Subject(s) - chemistry , piperazine , antimicrobial , candida albicans , staphylococcus aureus , bacteria , yeast , escherichia coli , stereochemistry , biphenyl , in vitro , minimum inhibitory concentration , combinatorial chemistry , organic chemistry , microbiology and biotechnology , biochemistry , genetics , gene , biology
A number of novel bicinnolines containing piperazine moieties, 4a – o , were synthesized via polyphosphoric acid‐catalyzed intramolecular cyclization of the respective acyl amidrazone derivatives ( 3a – o ). On the other hand, the amidrazones ( 3a – o ) were prepared by reaction of N ′, N ″‐(biphenyl‐4,4′‐diyl)bis(2‐oxopropane hydrazonoyl chloride) ( 2 ) with the appropriate cyclic sec ‐amines in the presence of trimethylamine in absolute ethanol. Structures of the newly synthesized compounds were confirmed by NMR and mass spectral data. The antitumor activity of compounds 4a – o was evaluated in vitro on human breast cancer MDA‐231 by a cell viability assay. Results revealed that compounds 4k , 4n , and 4o exhibit potential cytotoxic effects (>70%) on the cancer cells. Additionally, the antimicrobial activity of compounds 4a – o was evaluated against three clinical microbial strains: Escherichia coli (Gram‐negative bacteria), Staphylococcus aureus (Gram‐positive bacteria), and Candida albicans (fungi/yeast). Results revealed that compounds 4e and 4k exhibit good activity against all three strains included in the study and that compound 4d displays excellent activity against S . aureus strain with a minimum inhibitory concentration value of 0.187 mg/mL.