Synthesis, Spectroscopic Characterization, and Biological Evaluation of a Novel Acyclic Heterocyclic Compound: Anticancer, Antioxidant, Antifungal, and Molecular Docking Studies

Alhilal, Mohammad; Alhilal, Suzan; Sabancilar, Ilhan; Gomha, Sobhi M.; Elhenawy, Ahmed A.; Ouf, Salama A.

doi:10.3390/ph18101533

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Synthesis, Spectroscopic Characterization, and Biological Evaluation of a Novel Acyclic Heterocyclic Compound: Anticancer, Antioxidant, Antifungal, and Molecular Docking Studies

by

Mohammad Alhilal

¹

,

Suzan Alhilal

^2,*

,

Ilhan Sabancilar

³

,

Sobhi M. Gomha

^4,*,

Ahmed A. Elhenawy

^5,6

and

Salama A. Ouf

⁷

¹

Department of Nursing, Faculty of Health Sciences, Mardin Artuklu University, Mardin 47200, Turkey

²

Department of Medical Services and Techniques, Vocational School of Health Services, Mardin Artuklu University, Mardin 47200, Turkey

³

Department of Medical Services and Techniques, Vocational School of Health Services, Bitlis Eren University, Bitlis 13100, Turkey

⁴

Department of Chemistry, Faculty of Science, Islamic University of Madinah, Madinah 42351, Saudi Arabia

⁵

Chemistry Department, Faculty of Science, Al-Baha University, Al-Baha 65731, Saudi Arabia

⁶

Chemistry Department, Faculty of Science, Al-Azhar University, Cairo 11884, Egypt

⁷

Botany & Microbiology Department, Faculty of Science, Cairo University, Giza 12613, Egypt

^*

Authors to whom correspondence should be addressed.

Pharmaceuticals 2025, 18(10), 1533; https://doi.org/10.3390/ph18101533 (registering DOI)

Submission received: 24 August 2025 / Revised: 6 October 2025 / Accepted: 10 October 2025 / Published: 12 October 2025

(This article belongs to the Special Issue Heterocyclic Chemistry in Modern Drug Development)

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Abstract

Background/Objectives: This study aimed to synthesize a novel, high-molecular-weight acyclic heterocyclic compound, compound 5, via a one-pot reaction between Trichloroisocyanuric acid (TCCA) and ethanolamine, and evaluate its anticancer, antioxidant, and antifungal activities. Methods: Its complex tetrameric structure, assembled through N-N linkages, was unequivocally confirmed by a full suite of spectroscopic techniques including IR, ¹H & ¹³C NMR, ²D-NMR, and high-resolution mass spectrometry (LC/Q-TOF/MS). The MTT assay was used to assess the anticancer activity of compound 5 against four different human cancer cell lines. Results: The findings indicate that human colon (HT29) and ovarian (OVCAR3) cancer cells were sensitive to the treatment, whereas brain (glioblastoma) (T98G) cancer cells were resistant. The most pronounced cytotoxic effect was observed in pancreatic (MiaPaCa2) cancer cells. Notably, compound 5 exhibited potent antifungal properties, achieving 100% inhibition of the pathogenic water mould Saprolegnia parasitica zoospores at 100 µM after 10 min. Molecular docking studies corroborated the biological data, revealing a high binding affinity for key cancer and fungal targets (Thymidylate Synthase and CYP51), providing a strong mechanistic basis for its observed activities. Conclusions: These findings establish compound 5 as a promising dual-action agent with significant potential as both a targeted anticancer lead and an eco-friendly antifungal for applications in aquaculture.

Keywords: acyclic heterocyclic compound; trichloroisocyanuric acid; anticancer efficacy; antioxidant capacity; antifungal activity; molecular docking study

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MDPI and ACS Style

Alhilal, M.; Alhilal, S.; Sabancilar, I.; Gomha, S.M.; Elhenawy, A.A.; Ouf, S.A. Synthesis, Spectroscopic Characterization, and Biological Evaluation of a Novel Acyclic Heterocyclic Compound: Anticancer, Antioxidant, Antifungal, and Molecular Docking Studies. Pharmaceuticals 2025, 18, 1533. https://doi.org/10.3390/ph18101533

AMA Style

Alhilal M, Alhilal S, Sabancilar I, Gomha SM, Elhenawy AA, Ouf SA. Synthesis, Spectroscopic Characterization, and Biological Evaluation of a Novel Acyclic Heterocyclic Compound: Anticancer, Antioxidant, Antifungal, and Molecular Docking Studies. Pharmaceuticals. 2025; 18(10):1533. https://doi.org/10.3390/ph18101533

Chicago/Turabian Style

Alhilal, Mohammad, Suzan Alhilal, Ilhan Sabancilar, Sobhi M. Gomha, Ahmed A. Elhenawy, and Salama A. Ouf. 2025. "Synthesis, Spectroscopic Characterization, and Biological Evaluation of a Novel Acyclic Heterocyclic Compound: Anticancer, Antioxidant, Antifungal, and Molecular Docking Studies" Pharmaceuticals 18, no. 10: 1533. https://doi.org/10.3390/ph18101533

APA Style

Alhilal, M., Alhilal, S., Sabancilar, I., Gomha, S. M., Elhenawy, A. A., & Ouf, S. A. (2025). Synthesis, Spectroscopic Characterization, and Biological Evaluation of a Novel Acyclic Heterocyclic Compound: Anticancer, Antioxidant, Antifungal, and Molecular Docking Studies. Pharmaceuticals, 18(10), 1533. https://doi.org/10.3390/ph18101533

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Synthesis, Spectroscopic Characterization, and Biological Evaluation of a Novel Acyclic Heterocyclic Compound: Anticancer, Antioxidant, Antifungal, and Molecular Docking Studies

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