Startseite In silico DFT and molecular modeling of novel pyrazine-bearing thiazolidinone hybrids derivatives: elucidating in vitro anti-cancer and urease inhibitors
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In silico DFT and molecular modeling of novel pyrazine-bearing thiazolidinone hybrids derivatives: elucidating in vitro anti-cancer and urease inhibitors

  • Shoaib Khan ORCID logo , Rafaqat Hussain EMAIL logo , Yousaf Khan ORCID logo , Tayyiaba Iqbal , Saeed Anwar EMAIL logo , Tariq Aziz ORCID logo und Metab Alharbi
Veröffentlicht/Copyright: 1. Oktober 2024
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Abstract

In the present work, one of the leading health issues i.e. cancer was targeted by synthesizing and biologically investigating the potential of pyrazine-based thiazolidinone derivatives (1–13). The basic structure of the synthesized compounds was determined using a variety of spectroscopic techniques, including 1H NMR, 13C NMR, and HREI-MS. These scaffolds were studied for their biological profiles as anti-cancer as well as anti-urease agents. The biological effectiveness of these compounds was compared using the reference tetrandrine (IC50 = 4.50 ± 0.20 µM) and thiourea (IC50 = 5.10 ± 0.10 µM), respectively. Among novel compounds, scaffold 3, 6, 7 and 10 demonstrated an excellent potency with highest inhibitory potential (IC50 = 1.70 ± 0.10 and 1.30 ± 0.20 µM), (IC50 = 4.20 ± 0.10 and 5.10 ± 0.30 µM), (IC50 = 2.10 ± 0.10 and 3.20 ± 0.20 µM) and (IC50 = 2.70 ± 0.20 and 4.20 ± 0.20 µM), respectively, out of which scaffold 3 emerged as the leading compound due to the presence of highly reactive –CF3 moiety which interacts via hydrogen bonding. Molecular docking investigations of the potent compounds was also carried out which revealed the binding interactions of ligands with the active sites of enzyme. Moreover, the electronic properties, nucleophilic and electrophilic sited of the lead compounds were also studied under density functional theory (DFT).

Keywords: pyrazine; thiazolidinone; anti-urease; anticancer; DFT and molecular docking
Corresponding author: Rafaqat Hussain, Department of Chemistry, Hazara University, Mansehra, 21120, Pakistan, E-mail: ; and Saeed Anwar, Department of Chemistry, Abbottabad University of Science and Technology (AUST), Abbottabad, 22500, Pakistan, E-mail:

Acknowledgments

The authors greatly acknowledge and express their gratitude to the Researchers Supporting Project number (RSP2024R462), King Saud University Riyadh Saudi Arabia.

  1. Research ethics: The conducted research is not related to either human or animal use.

  2. Informed consent: Not applicable.

  3. Author contributions: Shoaib Khan: writing – original draft. Rafaqat Hussain: writing – review and editing. Yousaf Khan: methodology and investigation. Tayyiaba Iqbal: visualization and software. Saeed Anwar: characterization. Tariq Aziz & Metab Alharbi: writing – review and editing.

  4. Use of Large Language Models, AI and Machine Learning Tools: None declared.

  5. Conflict of interest: The authors declare no conflict of interest.

  6. Research funding: None declared.

  7. Data availability: Not applicable.

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Supplementary Material

This article contains supplementary material (https://doi.org/10.1515/znc-2024-0103).

Received: 2024-04-23
Accepted: 2024-09-05
Published Online: 2024-10-01
Published in Print: 2025-05-26

© 2024 Walter de Gruyter GmbH, Berlin/Boston

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  2. Review Articles
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  4. Exploring the functionality of fluorescent liposomes in cancer: diagnosis and therapy
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  7. Characterization and antimicrobial activity of essential oils extracted from lemongrass (Cymbopogon flexuosus) using microwave-assisted hydro distillation
  8. In silico DFT and molecular modeling of novel pyrazine-bearing thiazolidinone hybrids derivatives: elucidating in vitro anti-cancer and urease inhibitors
  9. Molecular mechanisms of the anticancer action of fustin isolated from Cotinus coggygria Scop. in MDA-MB-231 triple-negative breast cancer cell line
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https://doi.org/10.1515/znc-2024-0103
Schlagwörter für diesen Artikel
pyrazine; thiazolidinone; anti-urease; anticancer; DFT and molecular docking

Artikel in diesem Heft

  1. Frontmatter
  2. Review Articles
  3. Nourishment beyond grains: unveiling the multifaceted contributions of millets to United Nations Sustainable Development Goals
  4. Exploring the functionality of fluorescent liposomes in cancer: diagnosis and therapy
  5. Research Articles
  6. In vitro antibacterial activities, DPPH radical scavenging, and molecular simulation of isolated compounds from the leaves of Rhus ruspolii
  7. Characterization and antimicrobial activity of essential oils extracted from lemongrass (Cymbopogon flexuosus) using microwave-assisted hydro distillation
  8. In silico DFT and molecular modeling of novel pyrazine-bearing thiazolidinone hybrids derivatives: elucidating in vitro anti-cancer and urease inhibitors
  9. Molecular mechanisms of the anticancer action of fustin isolated from Cotinus coggygria Scop. in MDA-MB-231 triple-negative breast cancer cell line
  10. Green synthesized AgNPs of the Anchusa arvensis aqueous extract resulting in impressive protein kinase, antioxidant, antibacterial, and antifungal activities
  11. Phytochemical composition, antimicrobial, antioxidant, and wound healing activities of Thermopsis turcica
  12. Molecular detection of Coxiella burnetii infection (Q fever) in livestock in Makkah Province, Saudi Arabia
  13. Spermidine protects cellular redox status and ionic homeostasis in D-galactose induced senescence and natural aging rat models
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