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Vol. 35 No. 4 (2023): Vol 35 Issue 4, 2023

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Curcumin-Based Heterocycles: Synthesis, Antimicrobial Genotoxicity and Molecular Docking

https://doi.org/10.14233/ajchem.2023.26950
Rola Al-Kerm
Department of Chemistry, College of Science, An-Najah National University, Nablus, Palestine
Hisham Qrareya
Department of Chemistry, Arab American University, Jinin, Palestine
Othman Hamed
Department of Chemistry, College of Science, An-Najah National University, Nablus, Palestine
https://orcid.org/0000-0003-1074-2887
Ghaleb Adwan
Department of Biology, College of Science, An-Najah National University, Nablus, Palestine
Rana Al-Kerm
Department of Chemistry, College of Science, An-Najah National University, Nablus, Palestine
Omar Dagdag
Centre for Materials Science, College of Science, Engineering and Technology, University of South Africa, Johannesburg 1710, South Africa
https://orcid.org/0000-0002-9723-1344
Ashraf Sawafta
Department of Biology, College of Science, An-Najah National University, Nablus, Palestine

Corresponding Author(s) : Othman Hamed

ohamed@najah.edu

Asian Journal of Chemistry, Vol. 35 No. 4 (2023): Vol 35 Issue 4, 2023

Abstract

Curcumin is a natural compound with numerous biological activities and a precursor for many drugs. Development of a convenient one pot synthetic method for synthesizing curcumin-based diazepines and diazoles having antibacterial activities is focussed in this study. A one pot condensation process was developed for synthesizing a novel class of curcumin-based diazoles and diazepines by reacting curcumin with 2-diamino compounds and hydrazines in presence of sulfuric acid as catalyst. IR and 1H NMR were used to characterize the molecular composition of the synthesized curcumin derivatives. The synthesized derivatives were tested for their in vitro antibacterial efficacy against Gram-negative and Gram-positive bacteria. The MIC concentrations ranged from 1.56 to 200 μg/mL. Ampicillin exhibited synergistic effects with compounds C1, C3, C4 and C8. In the genotoxicity test, compound C3 was found to have no effect on the DNA molecules of E. coli strains, suggesting that it is not mutagenic and/or genotoxic. Compound C2 had the strongest interaction with the investigated protein receptor sites when blind molecular docking was conducted on all compounds. Since both H-donating and H-accepting sites of this molecule interact efficiently during the docking. In addition, absorption, distribution, metabolism and excretion (ADME) study showed that compound C2 do not contradict the Lipinski’s rule of drug likeness and showed a low level of passive human gastrointestinal absorption. The results indicated that C2 could be most promising among the studied compounds.

Keywords

Ampicillin Antimicrobial Benzodiazepine Curcumin Diazole Genotoxicity Molecular docking
Al-Kerm, R., Qrareya, H., Hamed, O., Adwan, G., Al-Kerm, R., Dagdag, O., & Sawafta, A. (2023). Curcumin-Based Heterocycles: Synthesis, Antimicrobial Genotoxicity and Molecular Docking. Asian Journal of Chemistry, 35(4), 951–960. https://doi.org/10.14233/ajchem.2023.26950
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