Synthesis, Antibacterial Activities and Theoretical Study of Polyhydroquinoline Derivatives
Muhammad Ismaila b c d✉, Rashid M Ahmadb d, Abdul Latifb d, Adnan Ali Khana b c d, Aftab Alamb d, Fethi Ahmet Özdemire f, Ammara Ammarab d, Mumtaz Alib d✉
- aCentral for Computational Materials Science, Dir Lower P.O. Box 18800 Khyber Pakhtunkhwa Pakistan
- bDepartment of Chemistry University of Malakand, Dir Lower P.O. Box 18800 Khyber Pakhtunkhwa Pakistan
- cCentral for Computational Materials Science, Dir Lower P.O. Box 18800, Khyber Pakhtunkhwa, Pakistan
- dDepartment of Chemistry, University of Malakand, Dir Lower, P.O. Box 18800, Khyber Pakhtunkhwa, Pakistan
- eDepartment of Molecular Biology and Genetics, Faculty of Science and Art Bingol University Bingol P.O. Box 12000 Turkey
- fDepartment of Molecular Biology and Genetics, Faculty of Science and Art, Bingol University, Bingol, P.O. Box 12000, Turkey
- ✉Corresponding author
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Abstract
Abstract In the present study, novel bis ‐Schiff base derivatives of polyhydroquinoline were synthesized through Hantzsch condensation reaction in excellent yields. Initially, a mixture of dimedone, ethyl acetoacetate, ammonium acetate and esterified aldehydes were refluxed in ethanol for 7–9 hrs. Then, hydrazine hydrate was treated with obtained polyhydroquinoline to form bis ‐hydrazide of corresponding polyhydroquinoline. Finally, the bis ‐hydrazide was independently refluxed with substituted aromatic aldehydes to get desired bis ‐Schiff base derivatives of polyhydroquinoline. The new derivatives were confirmed by modern spectroscopic techniques such as 1 H‐NMR, 13 C‐NMR and HR‐ESI‐MS. The targeted compounds were evaluated for their antibacterial activity using disc diffusion method. The derivative with four OH‐group was found more effective against Bacillus megaterium, Bacillus subtilis IM, Bacillus subtilis ATCC, Salmonella enterica and Proteus vulgaris FMC II with zone of inhibition 8.3, 7.6, 7.3, 6.6 and 6.3 mm, respectively. DFT study of targeted compounds were performed on both materials studio and Gaussian 09 package, which showed good agreement with experimental data. The NLO of synthesized compounds were calculated and consider good candidates for NLO. The global reactivity, NBO and 1 H‐NMR correlation were also studied, which showed good agreement. The cheap reagents, short reaction time and excellent yields are some features of current work.