Structural analysis of halogenated bicyclo[4.2.0] inositols, biological activities and molecular docking studies

The halogenated bicyclo[4.2.0] inositols (chiro-, scyllo- and muco-inositol derivatives) and a cyclic sulfate were obtained using cyclooctatetraene (COT). One of these structures (tetrol 12) was resolved by X-ray diffraction and the stereochemistry of the structure was determined. The antioxidant, anti-inflammatory and enzyme inhibition potentials of the six compounds were investigated. While all compounds show moderate antioxidant activity, they have a highly effective anti-inflammatory effect when compared to the standard drug ibuprofen. In addition, most of the compounds have considerable inhibitory potential on cholinesterase enzymes, although much more pronounced on α-glucosidase. Also, we performed molecular docking studies on AChE and BuChE enzymes for therapeutic alzheimer's patients and α-glocosidase enzymes for type-2 diabetes patients for enzyme inhibition. Cyclic Sulfate 10 is more active against AChE, BuChE and α-glocosidase, with calculated binding energies of -8.22, -7.58, and -6.59 kcal mol−1 respectively as compared to galantamine and acarbose standard for which the binding energy was calculated to be -8.14 (AChE), -7.53 (BuChE) and -4.84 (α-glocosidase) kcal mol−1, respectively.