VB1 Promoted Green Synthesis of Chalcones and its Neuroprotection Potency Evaluation

Abstract

For the first time, thiamine hydrochloride (VB1) has been employed as a catalyst for the synthesis of chalcones by metal-free Claisen–Schmidt condensation. Such an environmentally benign approach has several advantages such as a wide range of functional groups tolerance, a high yield of products, and the recoverability of this catalyst. Moreover, this unprecedented methodology enables the synthesis of the pharmaceutically important molecule 2′,4′-dihydroxy-6′-methoxy-3′,5′-dimethylchalcone (3f) and its derivatives. Moreover, 3f and its derivatives were screened for their preliminary in vitro neuroprotective activity against oxygen-glucose deprivation/reoxygenation (OGD/R)-induced apoptosis in SH-SY5Y cell lines. Most of the compounds exhibited the neuroprotective activity, and one of the prepared chalcones (3s), which incorporates prenyl moiety, showed the most potency by decreasing the expression of cleaved caspase-3, cleaved caspase-9, Bax, and p53 protein.