Novel Tricyclic Functionalized Azetidinone Molecules: Synthesis, Characterization and Evaluation of Antidepressant Action

Abstract

In order to assess the depression decreasing effect of the molecules, a forced swim protocol in rats was used to manufacture azetidinone compounds with a tricyclic nucleus. Three different procedures were used in order to synthesize the necessary compounds. Step one involved reacting anthracene-9,10-dione with hydrazine hydrate in the presence of methanol under refluxing conditions to produce 2. Next, several substituted aromatic aldehydes were refluxed with 2 under the influence glacial acetic acid as catalyst to create Schiff bases. Chloracetyl chloride was used under alkaline circumstances to accomplish cyclization in the last stage. The produced compounds 4a-e had a yield range from 61-70% and shown solubility or mild solubility in DMSO, methanol, and chloroform. Using methanol:ethyl acetate (4:6) as the solvent solution, TLC was used to evaluate the purity of the produced compounds. The compounds' Rf values ranged from 0.59 to 0.73. The compounds have a melting temperature range of 172-214°C and were produced as a white to yellow solid. The compounds demonstrated antidepressant activity that was dosage dependent. Compounds 4a, 4b, and 4d had significantly shorter immobility times (p<0.01) than the control group. It became clear that each test chemical may exhibit antidepressant activity when the dosage was increased.