Synthesis and Molecular Docking Studies of 2-arylideneindan-1,3-diones Derivatives as an Inhibitor of 17β-hydroxysteroid Dehydrogenase Type 1

Abstract

Due to the drawbacks of applying catalysts in the synthesis of α,β-unsaturated structure units and the importance of these materials, electrochemistry has been introduced as an efficient alternative.<br />Therefore, herein a high-yield synthesis of 2-arylideneindan-1,3-diones is proposed. The procedure is carried out in propanol, using electrons as a green catalyst for generating propanol anion as a base, to obtain indandione anion which readily underwent Knovenagel condensation with aromatic aldehydes. The affecting parameters such as current, reagent ratio and anode type were studied and their optimized amounts were observed to be 40 mA/cm2, benzaldehyde / indandion (3/1) and magnesium anode in an undivided cell at room temperature. The proposed method produces 2arylideneindan-1,3-diones directly from initial compounds in a safe and mild condition. All synthesized compounds were screened by molecular docking studies using the crystal structure of 17β-hydroxysteroid dehydrogenase type 1. Among products compound 4a depicted minimum binding energy and good affinity toward the active pocket of 17β-hydroxysteroid dehydrogenase type 1 compared to Equilin as a 17β-hydroxysteroid dehydrogenase inhibitor. <br /><br />