7-(4H-1,3-dioxin-2-yl)-8-hydroxy-9-methoxy-3-methyl-4H-chromeno[3,4-c]pyridin-5-one
[CAS# 2361297-58-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound
• Name: 7-(4H-1,3-dioxin-2-yl)-8-hydroxy-9-methoxy-3-methyl-4H-chromeno[3,4-c]pyridin-5-one
• Synonyms: D-F07
• Molecular Formula: C₁₈H₁₇NO₆
• Molecular Weight: 343.33
• CAS Registry Number: 2361297-58-5
• SMILES: CN1CC2=C(C=C1)C3=CC(=C(C(=C3OC2=O)C4OCC=CO4)O)OC

Discovory and Applicatios

7-(4H-1,3-dioxin-2-yl)-8-hydroxy-9-methoxy-3-methyl-4H-chromeno\[3,4-c]pyridin-5-one is a synthetic or semi-synthetic heterocyclic compound incorporating multiple fused ring systems and functional groups. The molecular structure includes a chromeno\[3,4-c]pyridin-5-one core, which consists of a fused chromene and pyridone ring, functionalized with hydroxy, methoxy, methyl, and dioxin substituents. This structural complexity contributes to the compound’s potential utility in medicinal chemistry, particularly in the exploration of pharmacological scaffolds with anti-inflammatory, anticancer, or neuroactive properties.

The chromeno\[3,4-c]pyridine skeleton is recognized in medicinal chemistry as a privileged scaffold, meaning it frequently appears in biologically active molecules across various therapeutic classes. Compounds containing this framework have demonstrated diverse biological properties, including inhibition of kinases, modulation of neurotransmitter receptors, and interference with inflammatory pathways. The fusion of a chromene ring with a pyridine often imparts enhanced binding affinity and specificity for enzyme active sites or receptor domains.

The 8-hydroxy and 9-methoxy substituents on the chromeno ring system can engage in hydrogen bonding and modulate electronic distribution, influencing the molecule's reactivity and interaction with biological targets. The presence of the methyl group at position 3 further affects the compound’s steric properties, which may impact selectivity or bioavailability in drug development contexts.

One of the most distinctive features of this compound is the presence of a 4H-1,3-dioxin-2-yl moiety at position 7. The 1,3-dioxin ring, being a six-membered heterocycle containing two oxygen atoms, is relatively rare in natural products and pharmaceuticals but is sometimes incorporated into synthetic molecules to improve solubility, metabolic stability, or receptor affinity. This moiety may also serve as a prodrug element or as a masked functional group that can undergo chemical transformation under physiological conditions.

Although no direct therapeutic agents based specifically on 7-(4H-1,3-dioxin-2-yl)-8-hydroxy-9-methoxy-3-methyl-4H-chromeno\[3,4-c]pyridin-5-one have been approved or widely studied in clinical contexts, its structure aligns with ongoing efforts to develop multifunctional molecules for complex disease targets. In academic and industrial research settings, such derivatives are often synthesized for screening against panels of enzymes or receptors, particularly those implicated in cancer, inflammation, or neurodegenerative disorders.

The synthesis of this compound typically involves multistep organic synthesis, starting from substituted chromene or pyridine intermediates. Key reactions may include cyclization, electrophilic aromatic substitution, and ring-closure processes that integrate the dioxin unit. Such synthetic efforts aim to explore structure-activity relationships and optimize physicochemical properties relevant to biological testing.

In summary, 7-(4H-1,3-dioxin-2-yl)-8-hydroxy-9-methoxy-3-methyl-4H-chromeno\[3,4-c]pyridin-5-one represents a complex heterocyclic compound of potential interest in medicinal chemistry. Its combination of electron-donating and electron-withdrawing substituents, along with a fused polycyclic scaffold, positions it as a candidate for further research in drug design, particularly in the early-stage identification of lead compounds with novel modes of action.