Novel Hybrid Heterocycles Based on 1,4-Diphenylpiperazine Moiety: Synthesis via Hantzsch and Biginelli Reactions, Molecular Docking Simulation, and Antimicrobial Activities
In this study, we have developed new hybrid compounds by connecting bis-heterocycles with the 1,4-diphenylpiperazine core. This is performed by combining 4,4'-(piperazine-1,4-diyl)-dibenzaldehyde with the necessary reagents via Hantzsch and Biginelli reactions. The structures of the newly synthesized compounds are determined by elemental analysis, <sup>1</sup>H NMR, <sup>13</sup>C NMR, IR, and mass spectrometry (MS) spectra. The antimicrobial activities of the tested compounds were evaluated. Compounds <b>10</b> and <b>39</b> exhibited notable antibacterial effects, whereas compound <b>15</b> showed antifungal activity, and compound <b>34</b> demonstrated antibacterial and antifungal properties. Molecular docking studies against tyrosinase (UniProt ID: P06845.TYRO_STRGA) revealed that compounds <b>10</b> and <b>39</b> achieved the highest binding affinity (Δ<i>G</i> = - 9.1 kcal/mol), forming 12 and 3 interactions, respectively.
Authors
- Nadeem Raza (ORCID: https://orcid.org/0000-0002-4433-8076)
- Hadeer M. Diab
- Ismail A. Abdelhamid (ORCID: https://orcid.org/0000-0003-1220-8370)
- Mostafa E. Salem (ORCID: https://orcid.org/0000-0003-4341-410X)
- Yassmen A. El-Gabry
- Mervat A. Abdel-Latif (ORCID: https://orcid.org/0000-0002-7996-0121)
- Ahmed H. M. Elwahy (ORCID: https://orcid.org/0000-0002-3992-9488)
- Mona M. Soliman
Institutions
- Cairo University (EG)
- Imam Mohammad ibn Saud Islamic University (SA)
- Institute of Botany (AM)
Publication Details
- Journal
- ACS Omega
- Published
- 2025-08-14
- DOI
- https://doi.org/10.1021/acsomega.5c05245
- Citations
- 6
- Primary Topic
- Synthesis and biological activity
- Type
- article
- Field-Weighted Citation Impact
- 5.62