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Updated: Jul 25, 2025
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Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
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Synthesis, Crystal Structure, DFT, and Anticancer Activity of Some Imine-Type Compounds via Routine Schiff Base
Jamal Lasri1, Naser E Eltayeb1, Saied M Soliman2
1Department of Chemistry, Rabigh College of Science and Arts, King Abdulaziz University, P.O. Box 344, Jeddah 21589, Saudi Arabia.
Molecules (Basel, Switzerland)
|June 28, 2023
Summary
Researchers synthesized novel imine compounds and an oxazine derivative, evaluating their anticancer potential. Compound 1 demonstrated the most significant anticancer activity against HepG2 and MCF-7 cell lines, showing promise for drug development.
Area of Science:
- Organic Synthesis and Medicinal Chemistry
- Materials Science and Crystallography
- Computational Chemistry and Molecular Modeling
Background:
- Imine derivatives and heterocyclic compounds are recognized for their diverse biological activities.
- The development of novel anticancer agents is crucial for combating cancer, a leading cause of mortality worldwide.
- Understanding structure-activity relationships is key to designing effective therapeutic compounds.
Purpose of the Study:
- To synthesize and characterize novel imine-type compounds and an oxazine derivative.
- To investigate the anticancer properties of the synthesized compounds against human cancer cell lines.
- To elucidate the structural features and intermolecular interactions influencing crystal packing and properties.
Main Methods:
- Synthesis of oximes and Schiff bases from substituted benzaldehydes and benzil derivatives.
- Structural characterization using single crystal X-ray diffraction and spectroscopic techniques (NMR).
- Evaluation of anticancer activity via cell viability assays (IC50 determination) and computational studies (DFT).
Main Results:
- Four compounds (1-4) were successfully synthesized, with structures 3 and 4 confirmed by X-ray diffraction.
- Hirshfeld analysis revealed significant O…H, N…H, and C…H interactions contributing to crystal stability.
- Compounds 1-4 exhibited anticancer activity against HepG2 and MCF-7 cells, with compound 1 showing the lowest IC50 values.
Conclusions:
- The synthesized imine and oxazine derivatives possess notable anticancer properties.
- Compound 1 is identified as a promising candidate for further development as an anticancer agent.
- Structural and computational analyses provide insights into the molecular basis of their activity and stability.
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
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