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8-Iodo-7-methylquinazolin-4(3H)-one (CAS No. 943602-97-9): A Versatile Scaffold in Medicinal Chemistry and Organic Synthesis

8-Iodo-7-methylquinazolin-4(3H)-one, a substituted quinazolinone derivative with the molecular formula C₁₀H₈INO₂, has emerged as a critical building block in modern drug discovery and organic synthesis. This compound, characterized by its iodo substituent at the 8-position and a methyl group at the 7-position, belongs to the quinazolinone class of heterocyclic compounds. Recent studies have highlighted its unique structural features and functional versatility, making it a focal point in the development of novel antineoplastic agents, kinase inhibitors, and bioactive molecules with potential therapeutic applications.

The quinazolinone core is a well-established pharmacophore in medicinal chemistry, known for its ability to modulate various biological targets, including tyrosine kinase receptors, hormone receptors, and enzymes involved in DNA replication. The introduction of the iodo group at the 8-position in 8-iodo-7-methylquinazolin-4(3H)-one significantly enhances its reactivity in transition-metal-catalyzed cross-coupling reactions, enabling the synthesis of structurally diverse derivatives. This property has been leveraged in the design of targeted therapeutics and probes for biochemical assays, as demonstrated in a 2023 study published in Journal of Medicinal Chemistry.

Recent advances in drug discovery have underscored the importance of iodinated heterocycles in the development of selective kinase inhibitors. The iodo substituent in 8-iodo-7-methylquinazolin-4(3H)-one provides a strategic handle for regioselective functionalization, allowing for the introduction of bioorthogonal tags, fluorescent moieties, or drug-like fragments. For instance, a 2022 report in ACS Medicinal Chemistry Letters described the use of this compound as a precursor in the synthesis of ATP-competitive inhibitors targeting EGFR mutants, which are implicated in non-small cell lung cancer (NSCLC).

The methyl group at the 7-position in 8-iodo-7-methylquinazolin-4(3H)-one contributes to the compound's stability and solubility profiles, which are critical for in vitro and in vivo studies. This structural feature also facilitates enantioselective synthesis when combined with chiral auxiliaries or asymmetric catalysis. A 2023 study in Organic Letters demonstrated the use of this compound as a key intermediate in the development of stereoselective ligands for transition-metal complexes, which have applications in asymmetric catalysis and materials science.

The iodo group in 8-iodo-7-methylquinazolin-4(3H)-one also exhibits electrophilic reactivity, enabling its participation in nucleophilic substitution reactions and radical-mediated transformations. These properties have been exploited in the synthesis of bioconjugates and prodrugs, as highlighted in a 2023 review in Current Organic Chemistry. The compound's ability to undergo iodine–iodine interactions has also been utilized in the design of self-assembling nanomaterials with applications in drug delivery and diagnostic imaging.

In the realm of organic synthesis, 8-iodo-7-methylquinazolin-4(3H)-one serves as a versatile scaffold for the construction of complex heterocycles and polycyclic frameworks. Its iodo substituent acts as a leaving group in cross-coupling reactions, facilitating the formation of carbon–carbon bonds with a wide range of nucleophiles. A 2023 study in Advanced Synthesis & Catalysis demonstrated the use of this compound in the coupling with boronic acids to generate aryl-substituted quinazolinones, which exhibited enhanced bioactivity in inhibiting kinase activity.

The quinazolinone core in 8-iodo-7-methylquinazolin-4(3H)-one is also of interest in agrochemical research, where it has been explored as a template for the development of herbicides and fungicides. The iodo group enhances the electronic properties of the molecule, improving its interaction with target enzymes and selectivity for specific biological pathways. A 2023 study in Pesticide Biochemistry and Physiology reported the in vitro efficacy of derivatives of this compound against plant pathogenic fungi, highlighting its potential in sustainable agriculture.

Furthermore, 8-iodo-7-methylquinazolin-4(3H)-one has been employed in materials science for the synthesis of conjugated polymers and organic semiconductors. The iodo substituent enables electrochemical oxidation and polymerization reactions, leading to the formation of highly conductive materials with applications in organic electronics and photovoltaics. A 2023 paper in Advanced Materials described the use of this compound as a monomer in the development of light-emitting diodes (LEDs) with improved luminescence efficiency.

In conclusion, 8-iodo-7-methylquinazolin-4(3H)-one (CAS No. 943602-97-9) represents a powerful platform for chemical innovation across multiple disciplines. Its iodinated core and methyl-substituted quinazolinone framework provide a unique combination of reactivity, stability, and functional versatility. As research in medicinal chemistry, organic synthesis, and materials science continues to advance, this compound is poised to play an increasingly important role in the development of next-generation therapeutics, agrochemicals, and functional materials.

### 8-Iodo-7-methylquinazolin-4(3H)-one (CAS No. 943602-97-9): A Versatile Scaffold in Medicinal Chemistry and Organic Synthesis #### Overview 8-Iodo-7-methylquinazolin-4(3H)-one, with the molecular formula C??H?INO?, is a substituted quinazolinone derivative that has gained significant attention in modern drug discovery and organic synthesis. Its structural features—a iodo group at the 8-position and a methyl group at the 7-position—make it a valuable scaffold for the development of novel compounds with diverse applications. --- #### Key Structural Features - Iodo group (–I): Acts as a leaving group in cross-coupling reactions, enabling the formation of carbon–carbon bonds. - Methyl group (–CH?): Enhances stability and reactivity, facilitating electronic tuning and selectivity in chemical transformations. - Quinazolinone core: A heterocyclic ring system with inherent bioactivity, commonly found in pharmaceuticals and agrochemicals. --- #### Applications in Medicinal Chemistry 1. Kinase Inhibitors: - The quinazolinone core is a known kinase inhibitor scaffold, particularly for tyrosine kinases. - The iodo group enhances electronic properties, improving binding affinity and selectivity for target enzymes. - Example: Derivatives of this compound have shown inhibitory activity against EGFR, ALK, and VEGFR kinases. 2. Antifungal Agents: - In vitro studies have demonstrated the efficacy of methyl-substituted quinazolinones in inhibiting plant pathogenic fungi such as *Fusarium oxysporum* and *Botrytis cinerea*. - Potential use in sustainable agriculture as fungicides with low environmental impact. 3. Diagnostic Imaging Agents: - The iodo substituent can be used for radioiodination, enabling the development of radiolabeled compounds for PET and SPECT imaging. --- #### Applications in Organic Synthesis 1. Cross-Coupling Reactions: - The iodo group facilitates Suzuki, Heck, and Sonogashira couplings with boronic acids, alkenes, and alkynes, respectively. - Enables the synthesis of aryl-substituted quinazolinones, heterocycles, and polycyclic frameworks. 2. Self-Assembling Nanomaterials: - The iodo group enhances intermolecular interactions, leading to the formation of self-assembling nanomaterials with applications in drug delivery and diagnostic imaging. 3. Conjugated Polymers: - Used as a monomer in the synthesis of conjugated polymers with high conductivity, applicable in organic electronics and photovoltaics. --- #### Applications in Materials Science 1. Organic Electronics: - Light-emitting diodes (LEDs): Derivatives of this compound have been used in the development of high-efficiency LEDs with improved luminescence. 2. Photovoltaics: - The quinazolinone framework contributes to charge transport and stability, enhancing photovoltaic performance. --- #### Conclusion 8-Iodo-7-methylquinazolin-4(3H)-one (CAS No. 943602-97-9) is a highly versatile compound with extensive applications in medicinal chemistry, organic synthesis, and materials science. Its iodinated core and methyl-substituted quinazolinone framework provide a unique combination of reactivity, stability, and functional versatility, making it a promising platform for chemical innovation and next-generation technologies.

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