(3aR,4R,5R,6aS)-4-[(1E)-4-(3-Chlorophenoxy)-3-oxo-1-buten-1-yl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one
[CAS# 53872-62-1]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Furan and pyran
• Name: (3aR,4R,5R,6aS)-4-[(1E)-4-(3-Chlorophenoxy)-3-oxo-1-buten-1-yl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one
• Molecular Formula: C₁₇H₁₇ClO₅
• Molecular Weight: 336.77
• CAS Registry Number: 53872-62-1
• SMILES: C1[C@H]([C@@H]([C@@H]2[C@H]1OC(=O)C2)/C=C/C(=O)COC3=CC(=CC=C3)Cl)O

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*, 1.418
• Index of Refraction: 1.637, Calc.^*
• Boiling Point: 537.8±50.0 °C (760 mmHg), Calc.^*
• Flash Point: 279.1±30.1 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovery and Applications

(3aR,4R,5R,6aS)-4-[(1E)-4-(3-chlorophenoxy)-3-oxo-1-buten-1-yl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one is a structurally intriguing compound belonging to the family of bicyclic molecules. This compound has gained attention in the field of medicinal chemistry due to its potential pharmacological applications, particularly in the treatment of ocular conditions.

The discovery of (3aR,4R,5R,6aS)-4-[(1E)-4-(3-chlorophenoxy)-3-oxo-1-buten-1-yl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one is rooted in the exploration of prostaglandin analogs, which are known for their diverse biological activities. The structural configuration of this compound includes a hexahydrocyclopentafuran framework, which is a key feature in determining its biological function. The compound’s stereochemistry, indicated by the R and S notations, is crucial as it influences its interactions with biological targets.

One of the most significant applications of this compound is its potential role as a therapeutic agent in managing ocular hypertension and glaucoma. The incorporation of the 3-chlorophenoxy group and the enone functionality in its structure is believed to enhance its affinity for prostaglandin receptors, promoting increased aqueous humor outflow and subsequently lowering intraocular pressure. This mechanism is analogous to that of other well-known prostaglandin analogs used in ophthalmic formulations.

Furthermore, the presence of the hydroxy group contributes to the compound's hydrophilicity, which is advantageous for formulation as an eye drop solution, enhancing its bioavailability in ocular tissues. As researchers continue to investigate the structure-activity relationship of this compound, it is anticipated that its effectiveness and safety profile can be optimized for clinical applications.

In addition to its use in ocular therapies, (3aR,4R,5R,6aS)-4-[(1E)-4-(3-chlorophenoxy)-3-oxo-1-buten-1-yl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one has potential as a precursor in the synthesis of other biologically active compounds. Its ability to undergo further chemical transformations, owing to its functional groups, makes it a valuable building block in organic synthesis.

In conclusion, (3aR,4R,5R,6aS)-4-[(1E)-4-(3-chlorophenoxy)-3-oxo-1-buten-1-yl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one represents a promising compound in medicinal chemistry with significant implications in ocular pharmacotherapy. As research progresses, it may offer new avenues for the development of effective treatments for conditions such as glaucoma, alongside serving as an important intermediate for synthesizing novel therapeutic agents.

References

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