New Hydrazide-hydrazone Derivatives of Quinoline 3-Carboxylic Acid Hydrazide: Synthesis, Theoretical Modeling and Antibacterial Evaluation

A series of biologically active 3-quinoline carboxylic acid hydrazide-hydrazones has been synthesized from 3-quinoline carboxylic acid hydrazide and a variety of aldehydes, with moderate to good yields. The chemical structures of the new products were confirmed by elemental analysis, IR, and H-1 NMR...

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Published inLetters in organic chemistry Vol. 16; no. 5; pp. 430 - 436
Main Authors Shabeeb, Ihsan, Al-Essa, Luay, Shtaiwi, Majed, Al-Shalabi, Eveen, Younes, Eyad, Okasha, Rouzi, Abu Sini, Mohammad
Format Journal Article
LanguageEnglish
Published SHARJAH Bentham Science Publ Ltd 01.01.2019
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
antibacterial activity
FMO
DFT
theoretical study
Hydrazide-Hydrazone
quinoline 3-Carboxylic acid
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Summary:A series of biologically active 3-quinoline carboxylic acid hydrazide-hydrazones has been synthesized from 3-quinoline carboxylic acid hydrazide and a variety of aldehydes, with moderate to good yields. The chemical structures of the new products were confirmed by elemental analysis, IR, and H-1 NMR, C-13 NMR spectral data. The structural and Frontier Molecular Orbital (FMO) properties and the Density Functional Theory (DFT) calculations were conducted for the new compounds. The new hydrazide-hydrazones exhibited low to moderate antibacterial activity against Staphylococcus aureus and Esherichia coli in comparison with gentamycin. Among the tested compounds, compounds 9 and 13 were found to be the most active. Phthalimide derivative 2 of 3-quioline carboxylic acid hydrazide showed remarkable antibacterial activity.
ISSN:1570-1786
1875-6255
DOI:10.2174/1570178616666181227122326