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

Abstract

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 alpha-glucosidase. Also, we performed molecular docking studies on AChE and BuChE enzymes for therapeutic alzheimer's patients and alpha-glocosidase enzymes for type-2 diabetes patients for enzyme inhibition. Cyclic Sulfate 10 is more active against AChE, BuChE and alpha-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 (alpha-glocosidase) kcal mol(-1), respectively. (C) 2021 Elsevier B.V. All rights reserved.